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Justus Lipsius
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Deepak Chopra
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Stephen Breyer
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Bernard Madoff
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Donald Cressey
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Todd Haugh*
“So why did Mr. Gupta do it?” That question was at the heart of Judge
Jed Rakoff’s recent sentencing of Rajat Gupta, a former Wall Street titan
and the most high-profile insider-trading defendant of the past thirty years.
The answer, which the court actively sought by inquiring into Gupta’s
psychological motivations, resulted in a two-year sentence, eight years less
than the government requested. What was it that Judge Rakoff found in
Gupta that warranted such a lenient sentence? While it was ultimately
unclear to the court exactly what motivated Gupta to commit such a
“terrible breach of trust,” it is exceedingly clear that Judge Rakoff’s search
for those motivations impacted the sentence imposed.
This search by judges sentencing white collar defendants—the search to
understand the “why” motivating defendants’ actions—is what this Article
When judges inquire into defendants’ motivations, they
necessarily delve into the psychological mechanisms defendants employ to
free themselves from the social norms they previously followed, thereby
allowing themselves to engage in criminality. These “techniques of
neutralization” are precursors to white collar crime, and they impact
courts’ sentencing decisions. Yet the role of neutralizations in sentencing
has been largely unexamined. This Article rectifies that absence by
drawing on established criminological theory and applying it to three
recent high-profile white collar cases. Ultimately, this Article concludes
that judges’ search for the “why” of white collar crime, which occurs
primarily through the exploration of offender neutralizations, is legally and
normatively justified. While there are significant potential drawbacks to
judges conducting these inquiries, they are outweighed by the benefits of
increased individualized sentencing and opportunities to disrupt the
mechanisms that make white collar crime possible.
* Visiting Assistant Professor of Law, IIT Chicago-Kent College of Law; 2011–2012
Supreme Court Fellow, Supreme Court of the United States. I would like to thank Douglas
Berman, Richard Beirshbach, Carissa Hessick, Michael Benson, J.C. Oleson, Christopher
Buccafusco, Steven Hayman, Kimberly Bailey, Wendy Epstein, Valerie Gutmann Koch,
David Schwartz, and Christopher Schmidt, as well as the participants of the “Punishment
and the Constitution” panel at the 2013 Law and Society Association’s Annual Conference,
the Chicago Law Schools’ Junior Faculty Workshop, and IIT Chicago-Kent’s Junior Faculty
roundtables, for comments and encouragement on early drafts.
[Vol. 82
INTRODUCTION ........................................................................................ 3144
A. Rajat Gupta............................................................................. 3150
B. Peter Madoff ........................................................................... 3153
C. Allen Stanford ......................................................................... 3157
II. NEUTRALIZATIONS AND WHITE COLLAR CRIME............................... 3160
A. Neutralization Theory ............................................................. 3160
B. A Taxonomy of White Collar Neutralizations ......................... 3165
SENTENCING ................................................................................. 3172
A. Legal Justification for Judicial Inquiry into Offender
Neutralizations ...................................................................... 3173
1. Evolution of White Collar Sentencing ............................. 3173
2. Pepper’s Impact on White Collar Sentencing.................. 3176
B. Normative Justification for Judicial Inquiry into
Offender Neutralizations....................................................... 3180
1. Increased Individualized Sentencing ............................... 3180
2. Disrupting the Mechanisms That Make
White Collar Crime Possible ........................................... 3186
CONCLUSION ........................................................................................... 3188
As he peered over his bench, Judge Jed Rakoff, Senior District Judge for
the Southern District of New York, faced one of the most high-profile
defendants of his long career. Rajat Gupta, the former managing director of
the global investment bank Goldman Sachs, the former head of the global
management consulting firm McKinsey & Company, and a former board
member of Proctor & Gamble, stood before the court to be sentenced.
Gupta, wearing a slight frown, looked haggard after his month-long trial
and conviction for passing inside information to hedge fund manager Raj
Rajaratnum, including about a $5 billion investment in Goldman by Warren
Buffet’s Berkshire Hathaway that allowed Rajaratnum to make millions in
illegal trades in less than two days.1 “After carefully weighing all . . .
relevant factors,” stated Judge Rakoff, “the Court concludes that the
sentence that most fulfills all requirements . . . is two years in prison.”2
Although he gave no visible reaction to the sentence, only rocking back
slightly on his heels, Gupta should have been relieved. He was the most
high-profile defendant in a four-year-long investigation of insider trading
1. See Michael Rothfeld & Dan Strumpf, Gupta Gets Two Years for Leaking Inside
Tips, WALL ST. J., Oct. 25, 2012, at A1; Peter Lattman, Ex-Goldman Director To Serve 2
Years in Insider Case, N.Y. TIMES DEALBOOK (Oct. 24, 2012, 4:17 PM), http://dealbook.
2. Sentencing Memorandum and Order at 14–15, United States v. Gupta, No. 11 CR
907 (S.D.N.Y. Nov. 9, 2012), ECF No. 128.
on Wall Street that had already seen sixty-eight others plead guilty or be
convicted, thirty-seven of whom would be serving prison time, including an
eleven-year sentence for Rajaratnum.3 The Federal Sentencing Guidelines
called for a much longer term, between six-and-a-half and eight years.4 The
government, citing Gupta’s “special responsibility that came with being in
such an extraordinary position of trust,” wanted ten.5
What was it that Judge Rakoff found in Gupta that warranted such a
lenient sentence? While the answer undoubtedly involves a “large complex
of facts and factors,”6 at least part of the reason rests on the court’s search
for the “why” of Gupta’s crimes. Throughout the sentencing hearing, Judge
Rakoff struggled to understand what motivated Gupta’s actions. Why had
an incredibly wealthy man in the uppermost echelon of American
financiers, who by all accounts had lived an exemplary life and given so
much to “humanity writ large,”7 committed a crime that provided him no
direct benefit? The court put it bluntly: “So why did Mr. Gupta do it?”8 In
attempting to answer that question, Judge Rakoff probed the statements
Gupta had made during his sentencing hearing, letters from his supporters,
and submissions from his attorneys, speculating about a host of possible
reasons why this “good man” committed such a “terrible breach of trust.”9
While it was ultimately unclear to the court exactly what motivated Gupta
to commit the crimes he did, it is exceedingly clear that Judge Rakoff’s
search for those motivations impacted the sentence imposed.10
3. See Rothfeld & Strumpf, supra note 1.
4. For an overview of the Federal Sentencing Guidelines and an explanation of how
they operate to calculate a defendant’s sentence, see Frank O. Bowman III, Pour Encourager
Les Autres?: The Curious History and Distressing Implications of the Criminal Provisions
of the Sarbanes-Oxley Act and the Sentencing Guidelines Amendments That Followed, 1
OHIO ST. J. CRIM. L. 373, 380–82 (2004).
5. Government’s Sentencing Memorandum, at 6, 12, Gupta, No. 11 CR 907, ECF No.
124. Most sentencing pundits predicted a sentence of four or five years. See, e.g., Douglas
A. Berman, Any Early Federal Sentencing Predictions After Quick Conviction in
Gupta Insider Trading Case?, SENT’G L. & POL’Y BLOG (June 16, 2012, 11:44 AM),
the “over/under betting line for Gupta’s sentencing at around 5 years’ imprisonment” and
then revising it to four years).
6. Sentencing Memorandum and Order, supra note 2, at 1.
7. Id. at 11.
8. Id. at 12. The government’s contention that Gupta was motivated by simple greed
did not seem plausible to Judge Rakoff given Gupta’s estimated net worth of $130 million
and that he received no direct benefit from the insider trades. See Peter Lattman & Azam
Ahmed, Rajat Gupta Convicted of Insider Trading, N.Y. TIMES DEALBOOK (June 15,
2012, 12:05 PM),
9. Lattman, supra note 1, at 1 (quoting Judge Rakoff).
10. See Sentencing Memorandum and Order, supra note 2, at 10 (“Thus, at the very
outset, there is presented the fundamental problem of this sentence, for Mr. Gupta’s personal
history and characteristics starkly contrast with the nature and circumstances of his
crimes.”); see also David A. Kaplan, Jed Rakoff: The Judge Who Rules on Business,
FORTUNE, Feb. 4, 2013, at 107, 108 (quoting Judge Rakoff as saying, “But also because of
what I think is an appropriate way to look at sentencing, which is, there are defendants who
are good people who have nevertheless done some bad things.”).
[Vol. 82
The search by judges sentencing white collar defendants—the search to
understand the “why” motivating defendants’ actions—is what this Article
aims to explore. When Judge Rakoff sought to understand Gupta’s
motivations, he necessarily delved into the psychological mechanisms white
collar defendants employ to free themselves from the social norms they
have previously followed, thereby allowing themselves to engage in
Criminologists call these mechanisms “techniques of
neutralization,” and they are precursors to white collar crime.11 Whether he
was aware of it or not, Judge Rakoff’s search to understand Gupta’s
motivations resulted in a judicial evaluation of the neutralization techniques
Gupta employed. The court’s crediting of these neutralizations as
mitigating sentencing factors was key to Gupta’s lenient punishment.
For example, in arriving at the two-year sentence, Judge Rakoff found
Gupta’s record of philanthropy to be a mitigating sentencing factor. After
listening to Gupta’s recitation of his prior good works during the sentencing
hearing and reading hundreds of supportive letters, Judge Rakoff concluded
that he had “never encountered a defendant whose prior history suggests
such an extraordinary devotion . . . to individual human beings in their
times of need.”12 While crediting a defendant’s good deeds at sentencing is
common in white collar cases, Judge Rakoff did something uncommon—he
suggested Gupta’s extensive good works may have played a role in
allowing his criminal behavior to go forward.13 By doing so, the court
identified and validated a neutralization technique common to white collar
offenders called the “metaphor of the ledger,”14 in which a defendant—
prior to engaging in the criminal act—internally catalogs his good works
and compares them to his potential future criminal conduct.15 This allows
11. See generally Shadd Maruna & Heith Copes, What Have We Learned from Five
Decades of Neutralization Research?, 32 CRIME & JUST. 221, 228–34 (2005) (providing an
overview of neutralization theory and its place in criminology); Gresham M. Sykes & David
Matza, Techniques of Neutralization: A Theory of Delinquency, 22 AM. SOC. REV. 664, 667
(1957) (originally positing neutralization theory and setting out five types of neutralizations).
12. Sentencing Memorandum and Order, supra note 2, at 12–13 (calling Gupta’s
behavior “aberrant”); see also Michael Rothfeld, Dear Judge, Gupta Is a Good Man, WALL
ST. J. (Oct. 12, 2012),
7804578052990875489744 (describing and linking to letters submitted on Gupta’s behalf);
Rajat Gupta’s Full Statement in Court, NDTV (Oct. 25, 2012),
13. See Sentencing Memorandum and Order, supra note 2, at 12–13 (“Gupta, for all his
charitable endeavors, may have felt frustrated . . . .”).
2004) (describing the metaphor-of-the-ledger neutralization and nine others that have been
identified as “free[ing] the delinquent from the moral bind of law so that he or she may now
choose to commit the crime”).
15. Much has been made in the criminological literature regarding whether offenders’
explanations of their behavior are after-the-fact rationalizations or pre-act neutralizations.
See Maruna & Copes, supra note 11, at 271 (calling this sequencing issue the “most
significant stumbling point for neutralization theory”). However, as explained in Part II.A
through II.B, infra, this is ultimately a false dichotomy. Any postoffense rationalization
offered by an offender, what we commonly call an “excuse,” is premised on beliefs drawn
from “society rather than something created de novo” by the offender. Maruna & Copes,
supra note 11, at 230 (quoting Sykes & Matza, supra note 11, at 669). Therefore, offenders’
the defendant to rationalize his future antinormative behavior, thereby
“blunt[ing] the moral force of the law” and allowing his criminal behavior
to proceed.16 Gupta’s use of this technique may have allowed him to see
himself as someone who had done more good in life than bad, thereby
reconciling the criminal acts he was committing with his self-image as an
upstanding member of society, a critical step in the process of committing a
white collar crime.17
The court’s identification and acceptance of Gupta’s neutralization and
the positive impact that had at sentencing raises a host of questions. For
one, how large an impact did crediting this single neutralization have on the
final sentence? Did the court consider other neutralizations Gupta may
have employed?18 If so, were they credited or rejected by the court and to
what degree? More broadly, do judges’ considerations of neutralizations
favor particular groups of defendants? Does this lead to unwarranted
sentencing disparity? Broader still, what are the potential costs and benefits
of basing sentencing decisions on inquiries into defendants’ neutralizations?
What place, if any, does this type of inquiry have in white collar sentencing,
or sentencing as a whole?
These questions, and the associated normative implications, have been
largely unexamined in legal scholarship.19 This is particularly troubling
because judges’ search for what motivates defendants to commit white
collar crime necessarily confronts offender neutralizations. Although this
Article does not endeavor to address all the questions raised above, it does
attempt to rectify the absence in scholarship by drawing on established
postoffense rationalizations express their pre-act rationalizations.
These pre-act
rationalizations—neutralizations—allow the illegal act to proceed. Id. at 271. Put another
way, “neutralizations [in general] might start life as after-the-fact rationalizations but
become the rationale . . . facilitating future offending.” Id. Given that very few white collar
crimes are single acts, but instead are made up of many small acts occurring over time, any
rationalization offered by an offender at the time of sentencing likely reflects that offender’s
pre- and inter-act thinking. See id.
16. Maruna & Copes, supra note 11, at 230; see also Michael L. Benson, Denying the
Guilty Mind: Accounting for Involvement in a White-Collar Crime, 23 CRIMINOLOGY 583,
584 (1985) (analyzing neutralizations used by four groups of white collar offenders).
17. See Benson, supra note 16, at 584.
18. See infra Part II.B for a taxonomy of white collar neutralization techniques.
19. While some fascinating work has been done regarding the role of motive in criminal
law and punishment, see, e.g., Carissa Byrne Hessick, Motive’s Role in Criminal
Punishment, 80 S. CAL. L. REV. 89 (2006), there has been almost no discussion of how
judges use evidence of motive to make sentencing decisions, let alone the more specific
issue of judicial inquiry into white collar offender neutralizations. See Ellen S. Podgor, The
Challenge of White Collar Sentencing, 97 J. CRIM. L. & CRIMINOLOGY 731, 747–48 (2007)
(discussing how motive may be, although often is not, a factor in punishment). As more
fully developed in Part II, infra, the neutralization processes defendants undertake, and on
which courts appear to base part of their sentencing determinations, are distinct from
motives. A white collar defendant’s motive is broader than the neutralizations he employs,
although both are related to the mental process facilitating the offense. Neutralizations are
accounts or verbalizations that allow an offender to act on his or her motivations. See Donald
R. Cressey, The Respectable Criminal, 3 CRIMINOLOGICA 13, 14–15 (1965) (describing an
offender’s motivation to commit a crime as involving three “essential kinds of psychological
processes,” one of which is a neutralization).
[Vol. 82
criminological theory and applying it to three recent high-profile white
collar cases.
Ultimately, this Article concludes that judges’ search for the why of
white collar crime, which occurs primarily through the exploration of
neutralizations that defendants employ, is legally and normatively justified.
While there are significant potential drawbacks to these inquiries, they are
outweighed by the benefits of increased individualized sentencing, the
importance of which has been recently reaffirmed by the U.S. Supreme
Court in Pepper v. United States.20 And, although counterintuitive,
neutralization inquiries may even disrupt the future commission of white
collar crime. Because when judges inquire into how defendants neutralize
their criminal behavior, but then reject those neutralizations as sentencing
mitigators (or treat them as aggravators), this lessens the ability of future
potential offenders to use those neutralizations to free themselves from the
moral bind of the law.21 Yet for these benefits to be realized in a fair and
transparent way, judges must be better educated as to the etiology of white
collar crime, understand how neutralizations are used by defendants,
consider the costs and benefits of basing sentencing decisions on
defendants’ neutralizations, and explain their decisionmaking processes.
Part I of this Article analyzes the sentencings of three high-profile white
collar offenders—Rajat Gupta, Peter Madoff, and Allen Stanford—
highlighting the courts’ inquiries into what motivated the defendants’
conduct. Part II draws on established criminological theory to provide a
framework for understanding the role of neutralizations in white collar
sentencing. It also provides a new taxonomy of neutralization techniques
specific to white collar crime that are at the heart of these judicial inquiries.
Part III addresses the legal and normative implications of courts taking
defendants’ neutralizations into account at sentencing, concluding that the
practice is justified yet not without potential costs.
Sentencing is not easy. This we know.22 Part of the reason sentencing is
so difficult is that it compels a judge to try and understand what motivated a
20. 131 S. Ct. 1229 (2011).
21. As explained in Part II.A, infra, white collar offenders must neutralize their future
criminal conduct in order to commit their offenses, otherwise they “could not free
themselves of the potential harm to their self-concept.” Maruna & Copes, supra note 11, at
22. Justice Kennedy, during a recent oral argument, stated the following: “The hardest
thing—as we know in the judicial system, one of the hardest things is sentencing.”
Transcript of Oral Argument at 46, Dorsey v. United States, 132 S. Ct. 2321 (2012) (No. 115683), available at But see MARVIN E. FRANKEL, CRIMINAL SENTENCES: LAW WITHOUT ORDER 15
(1973) (noting that while “[j]udges are commonly heard to say that sentencing is the
grimmest and most solemnly absorbing of their tasks,” they actually spend little time talking,
reading, or writing about sentencing issues).
defendant to commit the crimes charged.23 Sometimes there is an obvious
reason—addiction, mental health problems, an extensive social history of
abuse and neglect.24 But more often, a defendant’s motivations are less
clear, forcing the court to delve into the defendant’s personal history and
statements made at sentencing.25
The court’s inquiry is particularly difficult in white collar cases,26 in
which a judge is often faced with a seemingly successful and heretofore
law-abiding defendant who has nonetheless committed a serious crime.27
In these instances, the judge’s search for the defendant’s motivations
necessarily confronts the defendant’s expressed reasons for his conduct—
his rationalizations.28 The following descriptions of three recent white
23. In theory, judges could avoid this inquiry by basing sentencing decisions only on the
harm caused by defendants. However, even judges taking a strictly retributivist approach to
sentencing must confront defendants’ motivation to correctly assess blameworthiness, a
central focus of the retributivist when determining the proper level of just punishment. See
Hessick, supra note 19, at 112–13. Most federal judges consider a combination of
retributivist and consequentialist purposes when sentencing. See U.S. SENTENCING COMM’N,
2010 tbl.13 (2010), available at
24. See generally Todd Haugh, Can the CEO Learn from the Condemned? The
Application of Capital Mitigation Strategies to White Collar Cases, 62 AM. U. L. REV. 1
(2012) (discussing the use of social history investigations in white collar cases).
25. The main tool by which courts investigate defendants’ motivations is through the
Presentence Investigation Report (PSR) completed by the U.S. Probation Office. See OFFICE
(2006), available at PSRs are confidential documents prepared for the
sentencing judge detailing the offense conduct, impact to victims, defendant’s criminal
history, and defendant’s personal characteristics. Id. Letters submitted to the court are
another way a judge learns about the defendant.
26. There is a longstanding debate concerning the definition of “white collar crime.” See
Gilbert Geis, White-Collar Crime: What Is It?, in WHITE-COLLAR CRIME RECONSIDERED 31,
31–48 (Kip Schlegel & David Weisburd eds., 1992) (explaining the origins of various
definitions); Stuart P. Green, The Concept of White Collar Crime in Law and Legal Theory,
8 BUFF. CRIM. L. REV. 1, 3–13 (2004). Because the focus of this Article is on sentencing
white collar offenders, it adopts the definition used by the U.S. Sentencing Commission. See
White Collar Sentencing Data: Fiscal Year 2005—Fiscal Year 2009, 22 FED. SENT’G REP.
127, 127 (2009) (including most offenses punished under the fraud, antitrust, and tax
guidelines, but excluding offenses such as simple theft, shoplifting, failure to pay child
support, etc.).
27. Seventy-one percent of fraud offenders, which includes the vast majority of white
collar offenders, have little or no criminal history. See Selected Sentencing, Guideline
Application, and Demographic Information for § 2B1.1 Offenders, Fiscal Year 2012, U.S.
SENT’G COMM’N (Sept. 18, 2013),
28. Although the criminological literature often uses the terms motivation,
rationalization, and justification interchangeably, see, e.g., Maruna & Copes, supra note 11,
at 234–39, this Article treats the terms as distinct. As used here, motivation refers to what
inspires an offender to commit an illegal act; rationalization refers to the explanatory account
an offender offers of his illegal behavior (ex ante or ex post). Given its legal and normative
“baggage,” the term justification, which refers to the attempt by an offender to demonstrate
the correctness of his illegal behavior, is avoided when possible. However, as seen in Part
II.A, infra, neutralization theory blurs these distinctions.
[Vol. 82
collar sentencings demonstrate that judges are not only trying to understand
offender motivations, but they are crediting some rationalizations as
sentencing mitigators and rejecting others. The sentencings of Rajat Gupta
for insider trading, Peter Madoff for aiding his brother’s Ponzi scheme, and
Allen Stanford for fraud and money laundering highlight this judicial
inquiry and its variable effects on white collar sentences.29
A. Rajat Gupta
Indicted in October 2011, Gupta was the most high-profile defendant
charged with insider trading since junk bond–king Michael Milkin in the
1980s.30 The charges against Gupta centered around his alleged leaking of
boardroom secrets about Goldman and Procter & Gamble to Rajaratnam,
cofounder of the hedge fund Galleon Group and Gupta’s longtime friend
and business associate.31 According to the government, Rajaratnum gained
over $15 million in illegal trades based on Gupta’s tips.32 The government
alleged that Gupta was “motivated to assist” Rajaratnum and others at
Galleon because Gupta shared business interests with the hedge fund.33 A
jury ultimately found Gupta guilty of providing confidential information
related to two trades that Rajaratnum made.34 At sentencing, the
government asked for a prison term of 97 to 121 months, the range
prosecutors argued was required by the U.S. Sentencing Guidelines.35
29. The three sentencing “case studies” offered here are not intended to serve as a
substitute for a more robust qualitative or quantitative analysis of white collar sentencing or
judicial decisionmaking. Instead, the descriptions, drawn from cases that vary in terms of
offense conduct, geographic location, and procedural posture, are intended only to highlight
the inquiries judges undertake in white collar sentencings. Whether they are representative
of a broader range of white collar sentencings will depend on the results of a more
comprehensive review. That said, based on the author’s study of many white collar
sentencings, and his decade of experience defending white collar clients, these courts’
inquiries do appear to be typical in white collar cases.
30. See generally Sealed Indictment, United States v. Gupta, No. 11 CR 907 (S.D.N.Y.
Nov. 9, 2012), ECF No. 1 (charging Gupta with six counts of securities fraud and conspiracy
to commit securities fraud). The government filed a superseding indictment, expanding its
allegations of securities fraud in January 2013. Superseding Indictment, Gupta, No. 11 CR
907; see also Michael Bobelian, The Obscure Insider Trading Case That Started It All,
FORBES (Nov. 30, 2012, 11:52 AM),
31. See Superseding Indictment, supra note 30, at 6; Patricia Hurtado et al., ExGoldman Director Gupta Indicted on Fraud Charges, BLOOMBERG (Oct. 26, 2011, 1:03
32. Sentencing Memorandum and Order, supra note 2, at 9. Judge Rakoff ultimately
rejected this amount, finding Gutpa’s tips generated only $5 million in illegal gains.
33. Government’s Sentencing Memorandum, supra note 5, at 3–4 (contending that
Gupta invested tens of millions of dollars with Galleon-related entities and stood to make
substantial profits if the hedge fund was successful).
34. Chris Isidore, Gupta Convicted of Insider Trading, CNNMONEY (June 15, 2012,
4:33 PM), The
jury rejected the defense’s contention that there were legitimate reasons for Gupta and
Rajaratnum to be communicating. Gupta was also acquitted of two counts. Id.
35. Government’s Sentencing Memorandum, supra note 5, at 12. The range was driven
primarily by the monetary gain to Rajaratnum caused by Gupta’s tips. See Sentencing
Gupta, not surprisingly, argued for a much different sentence. On the
basis of over 400 letters submitted to the court, including by Bill Gates,
Kofi Annan, Deepak Chopra, and other luminaries in medicine, finance, and
government, the defense sought a sentence of probation with a significant
community service component.36 In letter after letter, writers detailed
Gupta’s extensive humanitarian efforts, including as chairman of three
international organizations.37 Gupta’s attorney called his client’s removal
from these organizations and various company boards a “fall from grace of
Greek tragic proportions,” contending that Gupta had “suffered punishment
far worse than prison already.”38 Gupta’s family members also submitted
letters to the court, relating personal stories of Gupta’s individual acts of
Gupta addressed the court at his sentencing hearing. He began by
focusing on the harm caused to his reputation “built over a lifetime” and the
“devastation” to his family by the verdict.40 Gupta also spoke of his many
good deeds, highlighting his individual acts of philanthropy.41 While not
citing the defense letters specifically, Gupta stated he was grateful for
family and friends that continued to support him.42 Notably, Gupta never
Memorandum and Order, supra note 2, at 9 (explaining that the gain amount was calculated
by the probation department and adopted by the government). According to the government,
a ten-year prison sentence was necessary to “reflect the seriousness of Gupta’s crimes and to
deter other corporate insiders in similar positions of trust from stealing corporate secrets and
engaging in a crime that has become far too common.” Government’s Sentencing
Memorandum, supra note 5, at 1. The government further argued that despite Gupta’s
apparent “deviation from an otherwise law-abiding life,” his two-year conspiracy to tip
Rajaratnum “displayed an above-the-law arrogance.” Id. at 6, 8.
36. Government’s Reply Sentencing Memorandum, United States v. Gupta, No. 11 CR
907 (S.D.N.Y. Nov. 9, 2012), ECF No. 26. Gupta’s sentencing memorandum and the
accompanying letters to the court were filed under seal; however, some letters and excerpts
from the defense memorandum were reported by the media. See Rothfeld & Strumpf, supra
note 1 (noting that Gupta’s attorneys argued for a sentence of probation and “rigorous”
community service in rural Rwanda).
37. See Letter from Kofi Annan to Jed S. Rakoff, Judge, U.S. Dist. Court for the S. Dist.
of N.Y. (Sept. 21, 2012), available at
letters-from-gates-and-annan-offer-support-for.pdf; Letter from Bill Gates to Jed S.
Rakoff, Judge, U.S. Dist. Court for the S. Dist. of N.Y. (July 24, 2012), available at Gupta served as chairman of the Global Fund to Fight AIDS, Tuberculosis, and
Malaria; the Public Health Foundation of India; and the United Nations Association of
America. The letters also referenced Gupta’s involvement with the Pratham Foundation,
which provides education to underprivileged children in India, and the Rockefeller
Foundation. See Sentencing Memorandum and Order, supra note 2, at 10.
38. Rothfeld & Strumpf, supra note 1, at 2.
39. See, e.g., Letter from Anita Gupta to Jed S. Rakoff, Judge, U.S. Dist. Court for the S.
Dist. of N.Y. (Sept. 4, 2012), available at
40. Rajat Gupta’s Full Statement in Court, supra note 12.
41. Id. Gupta stated: “I mentored many young people, and many more view me as a
role model,” and “I also often thought in particular about three not-for-profit organizations
that I was fortunate to help create.” Id.
42. Id.
[Vol. 82
admitted wrongdoing. The most he offered was that “the overwhelming
feelings in [his] heart [were] of acceptance of what ha[d] happened.”43
From the outset of Judge Rakoff’s remarks, it was clear he would not be
imposing a sentence within the Guidelines range. He began by rejecting the
Guidelines’ heavy reliance on monetary gain to establish the sentencing
range for an insider-trading offense.44 He reasoned that the heart of
Gupta’s offense, the abuse of his position of trust, was given too little
weight by the Guidelines.45 Equally as important, he found, the Guidelines
range did not “rationally square with the facts of this case.”46 Judge Rakoff
appeared to be searching for something more than what was expressed in
the Guidelines when making his sentencing decision.
The discussion then turned to the nature and circumstances of the offense
and Gupta’s personal history.47 Judge Rakoff speculated about the
motivations underlying Gupta’s crimes, acknowledging a “fundamental
problem” in many white collar cases: how to sentence a defendant who was
a “good man,” but who had committed a bad act.48 In an effort to reconcile
this duality, the judge rhetorically asked why Gupta “did it.”49
Judge Rakoff offered two possible reasons. One was that Gupta felt
frustrated in “not finding new business worlds to conquer,” allowing
himself to be enticed into sharing information with Rajaratnum, a fellow
South Asian executive on Wall Street who offered excitement and new
opportunities.50 The second reason is less clear. Hinting at information
presented to the court under seal, Judge Rakoff speculated that Gupta had
“begun to loosen his self-restraint in ways that clouded his judgment.”51
Judge Rakoff suggested, based on an “implicit suggestion,”52 that Gupta
43. Id. It is not surprising Gupta did not admit wrongdoing, as he had maintained his
innocence throughout the trial and filed an appeal of his conviction immediately after the
44. See Sentencing Memorandum and Order, supra note 2, at 4–9 (calling reliance on
gain “arbitrary” and “unsupported by any empirical data,” and calling into question the
“huge increase” in sentencing ranges for economic crimes since 1987). Judge Rakoff has
long-held views on the flaws in guidelines sentencing. See Nate Raymond, U.S. Commission
Reviews White-Collar Sentences, REUTERS (Sept. 17, 2013),
/2013/09/17/us-financial-crime-sentences-idUSBRE98G1D020130917 (stating that Judge
Rakoff “called for the guidelines to be ‘scrapped in their entirety’”).
45. See Sentencing Memorandum and Order, supra note 2, at 2.
46. Id. at 9.
47. See id. Section 3553 of the Sentencing Reform Act, the “bedrock of all federal
sentencing” according to Judge Rakoff, see id., requires judges to consider the nature and
circumstances of the offense and the history and characteristics of the defendant. 18 U.S.C.
§ 3553(a)(1) (2012).
48. Sentencing Memorandum and Order, supra note 2, at 10. Although not stated in the
written memorandum, it was widely reported that Judge Rakoff called Gupta’s crime
“disgusting in its implications.” Rothfeld & Strumpf, supra note 1.
49. Sentencing Memorandum and Order, supra note 2, at 12.
50. See id. at 12 (Judge Rakoff called Rajaratnum a “clever cultivator of persons with
information”); see also Every Bloody Indian Co-operated To Nail Me: Raj, TELEGRAPH
(Oct. 28, 2011),
51. Sentencing Memorandum and Order, supra note 2, at 12.
52. Id. Although unclear, this suggestion likely came from Gupta’s sentencing
memorandum filed under seal or letters from family members.
may have acted improperly because he “longed to escape the straightjacket
of overwhelming responsibility.”53 While Judge Rakoff ultimately could
not pinpoint what “was operating in the recesses of [Gupta’s] brain,” he
believed Gupta’s criminal acts were motivated by the prospect of “future
benefits, opportunities, and even excitement.”54
His inquiry into Gupta’s motivations complete, Judge Rakoff briefly
discussed additional sentencing factors and then imposed a two-year
sentence.55 Although Gupta did not receive probation,56 the sentence was
still strikingly lenient given the Guidelines range and the government’s
request.57 Exactly to what extent Judge Rakoff’s inquiry into Gupta’s
motivations impacted the final sentence is difficult to quantify, but the
judge’s statements indicate there was an impact. In fact, Judge Rakoff
appeared to directly credit two of Gupta’s expressed rationalizations as
mitigating sentencing factors: his relationship with and feelings of loyalty
to Rajaratnum, and his extensive good works compared to his aberrant
criminal behavior.58 In addition, Judge Rakoff intimated that he also found
Gupta’s suggestion that he had earned the right to engage in risky or
unethical behavior based on his many years of doing the right thing by
caring for others—the “loosen[ing] of self-restraint,” as the judge put it—to
be mitigating.59 In Gupta’s case, then, the court’s sentencing determination
appears to have been directly impacted by the rationalizations offered by
the defendant. Those rationalizations were credited by the court, resulting
in a sentence that was well below the Guidelines range.
B. Peter Madoff
If Gupta’s case demonstrates how a defendant’s rationalizations of his
crimes may be credited by the court at sentencing, Peter Madoff’s case
demonstrates how a court may credit some rationalizations and reject
others, resulting in little net impact at sentencing. The story of Peter
Madoff’s brother, Bernard, and his massive Ponzi scheme is well known.60
Beginning in the 1970s and ending in December 2008, Bernie Madoff,
founder of Bernard L. Madoff Investment Securities, ran the largest Ponzi
scheme in history, bilking thousands of individual and institutional
53. Id.
54. Id.
55. Id. at 13–15.
56. Rothfeld & Strumpf, supra note 1 (rejecting the idea of rigorous international
community service in place of imprisonment as “a kind of ‘Peace Corps for insider traders’”
(quoting Judge Rakoff)).
57. See Larry Neumeister, Ex-Goldman Exec’s 2-Year Sentence Draws Scrutiny,
ASSOCIATED PRESS (Oct. 25, 2012),
58. See Sentencing Memorandum and Order, supra note 2, at 12–13.
59. Id. at 12.
60. For a comprehensive analysis of Bernie Madoff’s scheme and the lies he told
[Vol. 82
investors out of billions of dollars.61 In June 2009, the seventy-one-yearold former chairman of the NASDAQ was sentenced to 150 years in prison
and ordered to forfeit $170 billion.62 The sentencing judge called his
crimes “extraordinarily evil.”63
While public outrage over the Madoff fraud focused on Bernie, questions
arose about who else knew his investment company was a sham. 64 At the
time of his arrest, Bernie told investigators that only he was to blame.65 But
three years later, Peter, the company’s chief compliance officer, pleaded
guilty to falsifying investment records and tax returns that enabled the
fraud.66 Peter also admitted to Judge Laura Swain that he prepared over
$300 million in investment redemptions to select employees, family, and
friends after his brother’s confession—three days before going to
prosecutors.67 However, Peter denied knowing that Bernie had been
operating a Ponzi scheme until he confessed.68 Pursuant to a plea
agreement, Peter consented to a $143.1 billion forfeiture order and a tenyear prison sentence.69
Because he had entered a plea agreement stipulating his punishment,
Peter’s statements and submissions to the court were aimed at ensuring that
Judge Swain accepted the agreed-upon sentence.70 Beginning with his plea
61. See Steve Fishman, The Madoff Tapes, N.Y. MAG., Mar. 7, 2011, at 24. Madoff’s
crimes are considered the “largest, longest and most widespread Ponzi scheme in history.”
Diana B. Henriques, Madoff, Apologizing, Is Given 150 Years, N.Y. TIMES, June 30, 2009, at
62. Henriques, supra note 61; Patricia Hurtado, Peter Madoff, Bernie’s Brother, To
Plead Guilty, BLOOMBERG (June 28, 2012),
63. Transcript of Sentencing Hearing at 47, United States v. Madoff, No. 09 CR 213
(S.D.N.Y June 29, 2009), available at
64. See Bernie Madoff: Lord of the Lies, ECONOMIST, May 21, 2011, at 87 (recounting
journalist Diana Henriques’s search for who else knew of Madoff’s fraud).
65. Hurtado, supra note 62.
66. See Peter Lattman & Ben Protess, In Guilty Plea, Peter Madoff Says He Didn’t
Know About the Fraud, N.Y. TIMES DEALBOOK (June 29, 2012, 8:16 PM), http://dealbook.
67. See Transcript of Plea Hearing at 38–39, United States v. Madoff, No. 10 Cr. 228
(S.D.N.Y. Dec. 21, 2012), available at
transcriptpetermadoffpleaproceeding%20.pdf; Lattman & Protess, supra note 66.
68. See Transcript of Plea Hearing, supra note 67, at 30 (“[I]t is important for your
Honor to know that at no time before December 2008 was I ever aware that my brother
Bernard Madoff, or anyone else at BLMIS, was engaged in a Ponzi scheme.”).
69. Id. at 22, 46. The $143.1 billion forfeiture amount does not reflect what Madoff
could pay, only the amount of money that passed through the investment company. Even the
widely reported $65 billion figure is misleading, because it includes the paper profits victims
believed they held in the fund. According to bankruptcy trustee Irving Picard, Madoff
customers had actual cash losses of $17.3 billion. See Peter Lattman & Diana B. Henriques,
Peter Madoff Is Sentenced to 10 Years for His Role in Fraud, N.Y. TIMES DEALBOOK (Dec.
20, 2012, 5:59 PM),
70. Despite a plea agreement between the defendant and the government, the sentencing
judge is the final arbiter of the sentence. See 18 U.S.C. § 3553(a) (2012); FED. R. CRIM. P.
11(c). Peter Madoff’s plea agreement acknowledged that the court was not bound by the
allocution and throughout the sentencing hearing, Peter took responsibility
for his crimes.71 However, he did offer a series of rationalizations. Stating
that he wanted to make the court aware of “some important background
facts that do not excuse my conduct, but that may help [the court]
understand why I am here today,” Peter described his relationship with his
brother.72 He explained that he always admired and looked up to Bernie,
who was seven years his senior, and believed him to be a “brilliant
securities trader.”73 He said he trusted Bernie “implicitly” during the
almost forty years he worked for him.74 But he also described how Bernie
controlled and demeaned him, personally and professionally.75 Numerous
letters from family, friends, and business associates confirmed that even
though Bernie was often “abus[ive]” to him, Peter “seemed to be blind to
his brother’s flaws.”76 Peter stated that after Bernie told him of the fraud,
he was “shocked and devastated, but nevertheless I did as my brother said,
as I consistently had done for decades.”77
Peter also highlighted his extensive good deeds. Through his sentencing
submissions, Peter recounted how he used his experiences as a cancer
survivor to help family members fight the disease, including his son and a
young niece and nephew.78 He also detailed his service to a facility aiding
agreement between the parties and the final sentence would be determined “solely” by Judge
Swain. Letter Agreement at 5, Madoff, No. 10 Cr. 228, available at
71. See Transcript of Plea Hearing, supra note 67, at 29–30 (“Your Honor, I am here
today to plead guilty to conspiracy and falsifying records of an investment adviser and to
accept responsibility for what I have done.”); see also Sentencing Memorandum at 3,
Madoff, No. 10 Cr. 228, ECF No. 296 (on file with Fordham Law Review) (“Peter Madoff
acknowledges without reservation that his offense conduct was wrong, is deeply ashamed,
and struggles to comprehend his circumstances and his own conduct.”); Transcript of
Sentencing Hearing at 22, Madoff, No. 10 Cr. 228, available at
usao/nys/madoff/cckfmads.pdf (“I accept full responsibility for my actions that have brought
me before your Honor today and I am here to accept my punishment from this Court.”).
72. Transcript of Plea Hearing, supra note 67, at 30.
73. Id. at 30.
74. Id. at 32–33. Peter explained how he convinced other family members to invest
millions in Bernie’s investment fund, which was lost when the fund collapsed. Id.
75. See id. at 33. The most obvious way was Bernie’s refusal to give Peter a financial
interest in the company he had helped build; another was Bernie’s criticism of Peter’s family
and religious devotion. See Sentencing Memorandum, supra note 71, at 21. Peter also
recounted that “Bernie was the boss,” and “[w]hen it came to business, no one could
question Bernie; Bernie would always have the last say: ‘My name is on the door.’” Id.
76. Sentencing Memorandum, supra note 71, at 21. One letter, which Peter stressed at
sentencing, is particularly telling of the relationship between the Madoffs:
When he spoke about Bernie, it sometimes sounded as if Peter was a young boy,
speaking about his idol. . . . I only knew Bernie as seen through Peter’s eyes. He
was the older brother who, when it came down to it, Peter worked for. The brother
Peter always wanted to please, the brother who would never really let Peter in, the
brother with the power. . . . Peter wanted to please others, and couldn’t see
himself as anything but the younger fat brother looking for approval from his idol.
Id. at 22.
77. Transcript of Plea Hearing, supra note 67, at 38–39.
78. See Sentencing Memorandum, supra note 71, at 24.
[Vol. 82
the elderly and to many causes related to the Jewish community.79 Peter’s
statements were buttressed by sixty-three letters from family and friends
describing his individual good deeds.80 This was in stark contrast to
Bernie’s sentencing, in which not a single supporting letter was submitted, a
fact Peter made clear to the court.81 Peter concluded by saying he was a
“good man” who made serious mistakes.82
Although not as explicitly as Judge Rakoff, Judge Swain also searched
for an explanation as to what motivated Peter to commit his crimes. In
determining whether the ten-year sentence was appropriate, Judge Swain
discussed at length the duality of Peter’s life.83 Alternatively applauding
him for his devotion to family and scolding him for enabling his brother’s
fraud, Judge Swain ultimately found Peter’s behavior “remarkable, but not
unique.”84 She suggested that only Peter could truly know the “story”
behind his actions, and she urged him to share it as a way to make amends
for his behavior.85 Judge Swain even suggested that Peter should become
more introspective so that he might understand the motivations underlying
his own criminal conduct.86
Judge Swain’s search for Peter’s motivations did not translate into a
lower sentence, however. The judge imposed the ten-year term as agreed to
by the parties.87 Yet it does appear Judge Swain credited at least two of
Peter’s rationalizations as sentencing mitigators. The first was his
subservient relationship with his brother. Judge Swain stated explicitly that
the court “underst[ood] that Peter Madoff’s relationship with his brother
Bernard was unhealthy.”88 Second was Peter’s extensive history of good
works compared to his criminal acts. The court found “much that [was]
good in [his] life,” specifically referencing his combination of community
work and devotion to family.89
At the same time, the court rejected Peter’s contention that he was not
responsible for his brother’s fraud because he had been misled. Calling him
a “sophisticated person who knew and knows right from wrong,” Judge
Swain found Peter’s contention that he did not know of the Ponzi scheme
79. See id. at 34–35 (calling Peter a “selfless and dedicated” board member of the Old
Westbury Hebrew Congregation, a “trusted participant” of the Central Synagogue in
Manhattan, and a “steady hand” on the board of the Lower East Side Tenement Museum).
80. See Reed Albergotti, Support for Madoff Brother, WALL ST. J., Dec. 18, 2012, at C3
(describing letters).
81. See Lattman & Protess, supra note 66.
82. Sentencing Memorandum, supra note 71, at 42.
83. See Transcript of Sentencing Hearing, supra note 71, at 29.
84. Id. at 29.
85. Id. at 29, 30.
86. See id. at 29–30 (recording Judge Swain as stating, “I recognize that you want to
understand what has happened,” and urging him to look inward to do so).
87. Id. at 32.
88. Id. at 28. The court was quick to state that the brothers’ relationship “cannot excuse
Peter Madoff’s conduct.” Id.
89. Id. at 31.
implausible.90 Judge Swain then challenged him to “be honest about all
that you have done and all that you have seen, in other words, about all that
you know.”91 In addition, Judge Swain rejected an implicit rationalization
that Peter appeared to be making—that his fraudulent acts were minor and
somehow acceptable when compared to the enormity of his brother’s Ponzi
As with the Gupta case, the exact impact of the court’s inquiry on Peter’s
final sentence is unclear. It is evident, however, that the judge grappled
with understanding Peter’s motivations and rationalizations. Judge Swain’s
acceptance of the ten-year sentence, despite conducting a lengthy inquiry
into Peter’s motivations, suggests she may have viewed his rationalizations
as offsetting. She may have credited two of Peter’s rationalizations (his
relationship with his brother and his prior good works), but offset them by
rejecting two others (denial of full responsibility and claim of relatively
acceptable conduct), resulting in no net change to the agreed-upon sentence.
C. Allen Stanford
The sentencing of Allen Stanford provides a third example of a court’s
consideration of a white collar defendant’s rationalizations of his conduct,
albeit with a much different result. Stanford, a brash Texas financier and
former chairman of Stanford Financial Group, was convicted in March
2012 of orchestrating a twenty-year-long scheme selling high-interest
certificates of deposit.93 Although his attorneys portrayed him as a
“visionary entrepreneur,” evidence at trial showed Stanford’s financial
empire that stretched from the United States to Latin America and the
Caribbean was a sham.94 Stanford used money invested in CDs issued by
his Antigua-based bank to fund a string of bad business ventures and real
estate deals, while at the same time buying multimillion-dollar yachts, a
fleet of jets, and a professional cricket team. 95 Following a six-week trial, a
jury found Stanford guilty of defrauding nearly 30,000 investors in 113
countries out of $7 billion.96 Repeatedly invoking comparisons to Bernie
90. Id. at 25. The court said Peter’s claim that he lacked knowledge of the scheme was
“beneath the dignity of the former vice chairman of NASD, governor of the National Stock
Exchange and corporate director, community pillar and family paradigm about whom I have
read so much.” The court added, “It is also, frankly, not believable.” Id. at 27–28.
91. Id. at 30.
92. See id. at 28; Sentencing Memorandum, supra note 71, at 20–23 (drawing
comparisons between Peter and Bernie Madoff).
93. See Nathan Vardi, Allen Stanford Convicted in $7 Billion Ponzi Scheme, FORBES
(Mar. 6, 2012, 1:49 PM),
94. See Juan A. Lozano, Allen Stanford Sentenced to 110 Years in Prison
for $7 Billion Ponzi Scheme, HUFFINGTON POST (June 14, 2012, 6:15 PM),
95. See id.
96. Clifford Krauss, Jury Convicts Stanford of 13 Counts in $7 Billion Ponzi Fraud,
N.Y. TIMES, Mar. 7, 2012, at B1. The government alleged that at the height of the fraud,
Stanford was stealing $1 million a day from the bank to prop up his failing personal
[Vol. 82
Madoff, prosecutors sought a prison term of 230 years.97 Stanford asked
for time served.98
If Peter Madoff provides an example of a defendant accepting
responsibility for his conduct, Stanford provides the counterexample.
Through his sentencing submissions, Stanford vehemently denied that he
operated a Ponzi scheme.99 He contended his company “actually made
investments” and had real value.100 In fact, he asserted the company would
have been able to fully meet its liabilities but for the government’s
intervention.101 In addition, he argued that he never actually promised
depositors he would make them profits or that any profits made would
come directly from their deposits.102 Stanford’s sentencing submissions
also attacked the government, accusing it of causing the company’s
downfall, of “spinning” the evidence to suggest a nonexistent Ponzi
scheme, and of engaging in “double-talk.”103 Finally, Stanford suggested
the government had targeted him to deflect attention away from its failure
to “uncover[] the shenanigans of the banks and other financial institutions
in 2008 and 2009.”104
At his sentencing hearing, in what can only be described as a “rambling”
address, Stanford denied that he had defrauded investors, attacking the
government for over forty minutes.105 He explained to Judge David Hittner
that he “was not a thief”; instead, it was the government’s “Gestapo tactics”
and insistence on making him a “scapegoat” for the “worldwide economic
collapse” that “destroyed a business that had real value.”106 He stated that
businesses. See David Benoit, Allen Stanford Sentencing: The Arguments From Both Sides,
WALL ST. J. (June 14, 2012, 1:10 PM),
97. United States’ Sentencing Memorandum at 1, United States v. Stanford, No. 4:09CR-00342-1 (June 14, 2012), ECF No. 866. The first line of the government’s sentencing
memorandum read, “Robert Allen Stanford is a ruthless predator responsible for one of the
most egregious frauds in history, and he should be sentenced to the statutory maximum
sentence of 230 years’ imprisonment.” Id; see also Transcript of Sentencing Proceedings at
40, Stanford, No. 4:09-CR-00342-1 (on file with Fordham Law Review) (presenting a victim
advocate’s argument that Stanford is more culpable than Madoff).
98. United States’ Sentencing Memorandum, supra note 97, at 1.
99. See Defendant’s Response to the Government’s Sentencing Memorandum at 2,
Stanford, No. 4:09-CR-00342, ECF No. 875 (on file with Fordham Law Review).
100. Id. at 3–4 (contending that Stanford Financial Group held, among other things, an
equity interest in Liat Airline).
101. See id. at 4 (“The fact is that right up to the intervention by the United States the
Bank had sufficient assets to meet its liabilities when taking into account liquid and nonliquid assets.”).
102. See id. at 5.
103. Id.
104. Id. at 6.
105. Krauss, supra note 96, at B1. At one point, the sentencing judge called a sidebar,
saying, “All right. I want to get this on the record. Mr. Stanford now is starting to ramble.”
Transcript of Sentencing Proceedings, supra note 97, at 40. Stanford explained at the
hearing’s outset that he had trouble organizing his thoughts after being severely injured in a
prison brawl and developing an addiction to painkillers. See id. at 26–29 (calling his ability
to remember events “Swiss cheese”).
106. Transcript of Sentencing Proceedings, supra note 97, at 31.
he “worked tirelessly and honestly” for thirty years building a “world class
financial services global company,” and that his bank was no different than
“the big banks whose CEOs and chairmen sit on the board of directors of
the Federal Reserve.”107 In addition, Stanford suggested he had been
singled out for prosecution because of his lack of political connections.108
He concluded by saying he was “at peace” with the way he “conducted
[him]self in business.”109 In response, the government called Stanford’s
version of events “obscene,” commenting that the “best argument for a
guideline sentence of 230 years just came from Allen Stanford.”110
Judge Hittner did not pause long before imposing sentence. He said the
evidence at trial demonstrated Stanford committed his crimes with the
“precise aim of amassing billions of dollars to fund a personal business
empire and to support an extraordinarily lavish lifestyle.”111 He then
sentenced Stanford to 110 years in prison.112 While not addressing
Stanford’s allocution in detail, it is evident that Judge Hittner rejected
Stanford’s rationalizations of his conduct.113 By framing Stanford’s
motivations as driven solely by greed,114 Judge Hittner dismissed three of
Stanford’s rationalizations: that others were responsible for investor losses,
that his investors were sophisticated and he was the real victim, and that the
government wrongly targeted him. Stanford also appeared to be offering a
fourth rationalization by suggesting that he had achieved much good in life
by building a successful international business, which Judge Hittner also
Stanford’s sentencing offers an example of a court considering but
rejecting the defendant’s proffered rationalizations for his conduct, leading
to an extremely lengthy sentence. This is in stark contrast to Rajat Gupta’s
sentencing, in which the court credited the defendant’s rationalizations
(even independently suggesting some) to impose a lenient sentence. Peter
Madoff’s sentencing falls somewhere in between—the court accepted some
rationalizations and rejected others, which likely had a negligible net impact
107. Id. at 30–31, 37.
108. See id. at 42 (“I was a formerly very rich, colorful, maverick Texan living in the
Caribbean who was a target and an easy target . . . not part of the Wall Street crowd. . . .
What I’ve seen very now close and personal is how that really works more so than I ever
thought. It’s who you know.”).
109. Id. at 43.
110. Id. at 44, 46.
111. Id. at 71.
112. Id. at 71–72. This places Stanford fourth on the list of the longest white collar
sentences, one below Madoff. See Liz Moyer, It Could Have Been Worse for Madoff,
FORBES (June 29, 2009, 10:25 AM), (describing the longest sentences of white
collar offenders).
113. Through his questioning of the government’s counsel and Stanford’s attorney at
various times during the sentencing hearing, Judge Hittner appears to have considered
Stanford’s rationalizations as they were raised, but quickly rejected each of them. See, e.g.,
Transcript of Sentencing Proceedings, supra note 97, at 47–52 (questioning whether
Stanford’s fraudulent conduct met the definition of a Ponzi scheme and how much
knowledge depositors possessed).
114. Id. at 53.
[Vol. 82
at sentencing. Common among each of these cases, however, is the court’s
inquiry into the defendant’s motivations and rationalizations, and that the
inquiry impacted the sentencing calculus. Assuming this is occurring in
other white collar cases, the next task is to understand exactly what judges
are searching for and what they may be finding that affects their sentencing
decisions. Criminological theory concerning the etiology of white collar
crime offers a compelling framework through which to analyze this aspect
of white collar sentencing.
A judge’s search for the why underlying a defendant’s white collar crime
necessarily begins with an inquiry into what motivated the defendant’s
actions. Prosecutors, such as those in the Stanford case, tend to argue that
white collar defendants are driven by simple, overwhelming greed.115 This
explanation, while having broad public appeal, is simplistic.116 Judges
realize, as evidenced by their willingness to consider many factors at
sentencing, including defendants’ motivations, that what causes—or
allows—a person to commit a white collar crime is varied and nuanced.
Criminological theory provides a framework to understand these causes. In
turn, neutralization theory helps illuminate what judges may be finding
during their sentencing inquiries that impact the sentences imposed.
A. Neutralization Theory
Understanding neutralization theory and how it helps explain white collar
crime and sentencing begins with the work of criminologist Donald
Cressey. Cressey, a former student of Edwin H. Sutherland, whose
groundbreaking work “invented the concept” of white collar crime, used a
study of embezzlers to develop a social psychological theory regarding the
etiology of “respectable” crime.117 Building on Sutherland’s theory of
differential association, which posited that criminal behavior involves
“motives, drives, rationalizations, and attitudes favorable to the violation of
law,”118 Cressey determined that three key elements are necessary for
115. See id. (noting the government’s argument that Stanford was “one of the greediest
criminals ever to appear for sentencing in a criminal case”). Professor Craig Haney has
identified this type of argument as part of the “crime master narrative” adopted by
prosecutors to sway sentencers. Craig Haney, Evolving Standards of Decency: Advancing
the Nature and Logic of Capital Mitigation, 36 HOFSTRA L. REV. 835, 841 (2008). While
greed undoubtedly plays a part in white collar crime, the “narrative” is a nuanced one. See,
PERSPECTIVE 71–72 (2009) (discussing research showing many white collar crimes are
committed not out of drive for additional material success, but out of the fear of losing
116. See Bowman, supra note 4, at 431–35 (describing the public and legislative reaction
to the Enron, WorldCom, and Tyco corporate scandals).
PSYCHOLOGY OF EMBEZZLEMENT, at x, 12 (1973); Cressey, supra note 19, at 13.
118. See Sykes & Matza, supra note 11, at 664; see also EDWIN H. SUTHERLAND, WHITE
COLLAR CRIME 240 (1983).
violations of a financial trust—the essence of white collar crime—to
First, Cressey theorized that an individual must possess a nonshareable
financial problem, i.e., a financial problem the individual feels cannot be
solved by revealing it to others.120 Second, the individual must believe that
the financial problem can be solved in secret by violating a trust, typically
by appropriating funds to which the individual has access through her
employment.121 Third, the individual must verbalize the relationship
between the nonshareable financial problem and the illegal solution in
“language that lets [her] look on trust violation as something other than
trust violation.”122 Put another way, the individual uses words and phrases
during an internal dialogue that makes the behavior acceptable in her mind
(such as by telling herself she is “borrowing” the money and will pay it
back), thus keeping her perception of herself as an honest citizen intact.123
Cressey called the verbalizations described in his third element “the crux
of the problem.”124 According to him, the words that the potential white
collar offender uses during her conversations with herself are “actually the
most important elements in the process which gets [her] into trouble, or
keeps [her] out of trouble.”125 Cressey did not view these verbalizations as
simple, after-the-fact excuses that offenders use to relieve their culpability
upon being caught.
Instead, he found the verbalizations were
“[v]ocabularies of motive,” words and phrases not invented by the offender
“on the spur of the moment,” but that existed as group definitions labeling
deviant behavior as appropriate.126 This meant, he suggested, that an
offender’s rationalizations were created before acting. “The rationalization
is [her] motivation”—it not only justifies her behavior to others, but it
makes the behavior intelligible, and therefore actionable, to herself.127
119. See Cressey, supra note 19, at 14.
120. See id. Cressey explained that the problem may not seem dire from the outsider’s
perspective, but “what matters is the psychological perspective of the potential [white collar
criminal].” Id. Thus, problems may vary in type and severity, from gambling debts to
business losses, which the individual is ashamed to reveal. Cressey’s definition of a
nonshareable problem encompasses notions of greed. See JAMES WILLIAM COLEMAN, THE
CRIMINAL ELITE 195 (5th ed. 2002) (arguing that of Cressey’s three elements, the first is the
“most questionable, for there appears to be no necessary reason why an embezzlement must
result from a nonshareable problem instead of a simple desire for more money”).
121. See LANIER & HENRY, supra note 14, at 168; Cressey, supra note 19, at 14–15.
122. Cressey, supra note 19, at 15.
123. See id.
124. Id.
125. Id.
126. See id. Cressey’s discussion of vocabularies of motives drew from the work of C.
Wright Mills’s and Edwin Sutherland’s “definitions favorable to violations of law.”
CRESSEY, supra note 117, at viii.
127. CRESSEY, supra note 117, at 94, 95. Cressey explained that his interviews of
embezzlers revealed “significant rationalizations were always present before the criminal act
took place, or at least at the time it took place, and, in fact, after the act had taken place the
rationalization often was abandoned.” Id. at 94.
[Vol. 82
Cressey explained that verbalizations permit behavior that would otherwise
be unavailable or unacceptable to the offender.128
Shortly after Cressey published his theories, Gresham Sykes and David
Matza advanced a sophisticated theory of delinquency focused on how
juvenile delinquents rationalize their behavior. Their influential study
found that great flexibility exists in criminal law; values and norms appear
not as absolutes, but as qualified guides for action.129 Pointing to the
various defenses to criminal liability, such as necessity, insanity, and selfdefense, they argued that this flexibility allows offenders to avoid moral
culpability and negative societal sanctions by demonstrating to themselves
their lack of criminal intent.130 Sykes and Matza believed that most
antinormative behavior was based on “what is essentially an unrecognized
extension of defenses to crimes, in the form of justifications for deviance
that are seen as valid by the delinquent but not by the legal system or
society at large.”131 In other words, delinquents justify or rationalize their
behavior to fit it within a “defense” they deem valid but that larger society
may not.132
Like Cressey, Sykes and Matza found that while rationalizations may
occur following deviant behavior, they also precede behavior and make it
possible.133 By rationalizing their conduct ex ante, thus creating pre-act
defenses, offenders are able to neutralize the “[d]isapproval flowing from
internalized norms and conforming others in the social environment.”134
Sykes and Matza called these rationalizations “techniques of
neutralization,” and they believed they explained the episodic nature of
delinquent behavior more completely than competing theories.135
Neutralizations explained how offenders could “remain[] committed to
society’s dominant normative system,” yet qualify that system’s
imperatives in a way to make periodic violations “‘acceptable’ if not
‘right.’”136 Neutralization theory and its core idea—that the mechanisms
128. See id. at 153. Cressey conducted interviews with inmates at three penitentiaries
who were incarcerated for crimes defined as “the criminal violation of financial trust.” Id. at
22. One hundred and thirty-three inmates were interviewed multiple times and for multiple
hours to understand the motivations underlying their crimes. Id. at 25. Although
criminological studies such as Cressey’s often rely on such qualitative interviews, concerns
regarding sample selection and generalizability should not be ignored. See Maruna & Copes,
supra note 11, at 260–70 (discussing the pros and cons of interview-based, survey-based,
and quantitative neutralization research).
129. See Sykes & Matza, supra note 11, at 666.
130. Id.
131. Id.
132. Id.
133. See id.
134. Id.
135. Id. at 667. For a list mainstream criminology’s theoretical approaches to
understanding the causes of crime, see FRANK E. HAGAN, INTRODUCTION TO CRIMINOLOGY:
136. Sykes & Matza, supra note 11, at 667. Key to neutralization theory is the concept of
“drift,” which Matza developed in his solo work. The idea is that offenders are able to drift
in and out of delinquency by using neutralization techniques that “free[] the individual from
the moral bind of law and order.” Maruna & Copes, supra note 11, at 231.
offenders use to rationalize their behavior are a critical component in the
etiology of criminal behavior—has greatly influenced the study of crime.137
Although neutralization theory was specifically developed in the context
of juvenile delinquency, it has particular force in explaining white collar
crime. As an initial matter, neutralization theory has its roots in the study
of “respectable” crime. The theory stems from Cressey’s ideas regarding
the verbalizations that trust-violators employ, which he identified as the
most important of the elements necessary for white collar crime.138 Indeed,
Sykes and Matza recognized that neutralization techniques might be used
not only by juveniles, but also by adults engaged in general forms of
deviance, including those committing crimes in the workplace.139
More fundamentally, neutralization theory is especially applicable in
describing the etiology of white collar crime because “almost by definition
white-collar offenders are more strongly committed to the central normative
structure.”140 They are older, more educated, better employed, and have
more assets than other offenders.141 These factors suggest that white collar
offenders are able to conform to normative roles and have a self-interest in
doing so—they have a “greater ‘stake’ in conformity” than many other
offenders.142 It is therefore reasonable to assume that white collar offenders
must rationalize their behavior through “elaborate neutralization processes
prior to their offenses.”143 Without employing neutralizations, white collar
offenders would be unable to “bring [their] actions into correspondence
with the class of actions that is implicitly acceptable in . . . society.”144 Not
137. See Maruna & Copes, supra note 11, at 222. Shadd Maruna and Heith Copes state
that the “influence of this creative insight has been unquestionable.” Id. Indeed, Sykes and
Matza’s article is one of the most-cited explanations of criminal behavior in the first part of
the twenty-first century, and their theories have been applied in a variety of contexts. Id. at
222–23 (“It is clear that neutralization theory ‘transcends the realm of criminology.’”
(quoting Moshe Hazani, The Universal Applicability of the Theory of Neutralization:
German Youth Coming to Terms with the Holocaust, 15 CRIME L. & SOC. CHANGE 135, 146
138. See Cressey, supra note 19, at 14, 16. While acknowledging his theories were
developed only to fit the crime of embezzlement, Cressey believed “the verbalization
section . . . will fit other types of respectable crime as well.” Id. at 16. This makes sense
given that Cressey’s theories arose out of Sutherland’s work on white collar crime. Sykes
and Matza cite to both Sutherland and Cressey in their seminal article. See Sykes & Matza,
supra note 11, at 664 n.1, 669 n.14.
139. See William A. Stadler & Michael L. Benson, Revisiting the Guilty Mind: The
Neutralization of White-Collar Crime, 37 CRIM. JUST. REV. 494, 496 (2012) (explaining the
applicability of Sykes and Matza’s theories to white collar offending).
140. Benson, supra note 16, at 587. Of course, defining what exactly is society’s central
normative structure is problematic. As used here, it means only a law-abiding structure.
141. See BENSON & SIMPSON, supra note 115, at 51–52.
142. Scott M. Kieffer & John J. Sloan III, Overcoming Moral Hurdles: Using Techniques
of Neutralization by White-Collar Suspects As an Interrogation Tool, 22 SEC. J. 317, 324
143. Benson, supra note 16, at 587.
144. Id. at 588.
[Vol. 82
surprisingly, numerous studies have documented the use of neutralizations
by white collar criminals.145
In addition, neutralization theory is particularly compelling in the context
of white collar crime because of where neutralizations originate.
Criminologists believe that the rationalizations offenders use are not created
in a vacuum; instead, offenders find the “vocabularies” they use to
neutralize their future criminal behavior from their environment.146
Cressey explained that these rationalizations are “taken over” from “popular
ideologies that sanction crime in our culture.”147 Sykes and Matza
suggested that neutralizations are learned from the legal system itself. With
its reliance on lack of intent defenses, they contended, “[t]he law contains
the seeds of its own neutralization.”148 This seems particularly true for
white collar crimes. Intent is almost always an offense element and most
defenses are premised on its alleged absence.149 Also, the environments in
which white collar offenders operate provide a source of learned
neutralizations. This could be the corporate capitalist environment
generally,150 or a specific occupational subculture in which an offender
145. See Maruna & Copes, supra note 11, at 223; see also Benson, supra note 16, at 591–
98 (finding antitrust, tax, financial trust, fraud, and false statements offenders were “nearly
unanimous” in neutralizing their criminal conduct by “denying basic criminality”); Petter
Gottschalk, Rotten Apples Versus Rotten Barrels in White Collar Crime: A Qualitative
Analysis of White Collar Offenders in Norway, 7 INT’L J. CRIM. JUST. SCI. 575, 580–81
(2012) (applying neutralization theory in a study of Norwegian white collar offenders);
Kieffer & Sloan, supra note 142, at 318–24 (arguing that neutralizations are particularly
important for white collar offenders); Stadler & Benson, supra note 139, at 495–98 (listing
the domains in which researches have explored the use of neutralizations, including
occupational deviance, corporate crime, and other forms of white collar offending); Paul
Michael Klenowski, “Other People’s Money”: An Empirical Examination of the
Motivational Differences Between Male and Female White Collar Offenders, at iv (May
2008) (unpublished Ph.D. dissertation, Indiana University of Pennsylvania) (on file with
Fordham Law Review) (studying neutralization techniques employed by male and female
white collar trust violators).
146. LANIER & HENRY, supra note 14, at 169–70; Cressey, supra note 19, at 15. Michael
Benson stated it this way: “[T]he offender . . . must bring his actions into correspondence
with the class of actions that is implicitly acceptable in his society. For this reason, accounts
should not be thought of as solely individual inventions.” Benson, supra note 16, at 588.
147. Cressey, supra note 19, at 15.
Cressey argued that once antinormative
verbalizations, such as “‘[a]ll people steal when they get in a tight spot,’” are assimilated and
internalized by an individual, they take on a more personal bent, allowing the individual to
act without disrupting her self-perception as an honest individual. Id.
supra note 14, at 170; Sykes & Matza, supra note 11, at 666.
149. See, e.g., Dan Markel, Retributive Damages: A Theory of Punitive Damages As
Intermediate Sanction, 94 CORNELL L. REV. 239, 314 (2009) (describing “ambiguous areas
of moral wrongdoing sometimes associated with white-collar misconduct”); Q&A with
Morgan Lewis’ Eric Sitarchuk, LAW360 (Feb. 28, 2013),
418509/q-a-with-morgan-lewis-eric-sitarchuk (“In white collar cases . . . the issue is often
whether a crime even occurred—which often turns on a careful analysis of what the
circumstantial says about criminal intent . . . .”).
150. See Benson, supra note 16, at 588 (“The widespread acceptance of such concepts as
profit, growth, and free enterprise makes it plausible for an actor to argue that governmental
regulations run counter to more basic societal values and goals. Criminal behavior can then
be characterized as being in line with other higher laws of free enterprise.”).
works.151 These environments provide its “members with a set of
appropriate rationalizations . . . [and] help to isolate them from contact with
those who would pass harsher judgment on their criminal activities.”152
While it is certainly true that many types of offenders rationalize their
criminal behavior, neutralization theory’s relevance in understanding white
collar crime is especially strong.
B. A Taxonomy of White Collar Neutralizations
Given neutralization theory’s strength in explaining white collar crime, it
follows that white collar offenders must neutralize their illegal conduct in
order to effectuate their crimes. This Article identifies eight neutralization
techniques employed by white collar criminals, some of which will be
familiar from the discussion of the Gupta, Madoff, and Stanford cases.153
The discussion below also provides insight into which neutralizations
judges may be crediting or rejecting as part of the sentencing process.
Denial of Responsibility. Called the “master account,” the denial of
responsibility neutralization entails the offender defining his conduct in a
way that relieves him of responsibility, thereby mitigating “both social
disproval and a personal sense of failure.”154 Generally, offenders deny
responsibility by claiming their behavior is accidental or due to forces
outside their control.155 White collar offenders deny responsibility by
pleading ignorance, suggesting they were acting under orders, or
contending larger economic conditions caused them to act illegally.156 The
complexity of laws regulating many white collar crimes and the hierarchical
151. See COLEMAN, supra note 120, at 199; Benson, supra note 16, at 591–98 (describing
occupational cultures that promote specific neutralization techniques); Kieffer & Sloan,
supra note 142, at 324 (“[A] group in which the offender has membership may sanction a
particular trust violation, and the offender may then take that general acceptance, apply it to
his or her own situation, and thus rationalize it because the group sanctioned it. This
concept is especially applicable to white-collar crime, where learning neutralizations may
take place as part of routine professional socialization processes that occur in complex
152. COLEMAN, supra note 120, at 199.
153. Sykes and Matza originally identified five major types of neutralization techniques.
See Sykes & Matza, supra note 11, at 667–70. These “famous five” neutralizations are the
first five discussed below. As neutralization theory has progressed, some criminologists
have criticized the list as not conceptually distinct enough, thereby causing problems for
future research. See Maruna & Copes, supra note 11, at 284 (arguing that the original list of
five techniques are not theoretically precise). Currently, researchers have identified between
fifteen and twenty techniques. It is difficult to make a definitive count because some
techniques appear to overlap or are described inconsistently by researchers. See Maruna &
Copes, supra note 11, at 234; Stadler & Benson, supra note 139, at 496–98.
154. Maruna & Copes, supra note 11, at 231–32.
155. See id. at 232; Sykes & Matza, supra note 11, at 667 (“By learning to view himself
as more acted upon than acting, the delinquent prepares the way for deviance from the
dominant normative system without the necessity of a frontal assault on the norms
156. See Kieffer & Sloan, supra note 142, at 320–21 (explaining how white collar
offenders blame violations on personal problems, such as alcoholism, drug addiction, or
perceived financial difficulties); Maruna & Copes, supra note 11, at 232; Sykes & Matza,
supra note 11, at 667.
[Vol. 82
structure of companies offer offenders numerous ways to diffuse their
responsibility.157 Both Peter Madoff and Allen Stanford appear to have
neutralized their conduct by denying responsibility—Madoff by asserting
his brother misled him and Stanford by asserting the global financial
downturn and government intervention caused investor losses. Neither
Judge Swain nor Judge Hittner appears to have accepted this neutralization
as a mitigating sentencing factor.158
Denial of Injury. This neutralization technique focuses on the injury or
harm caused by the illegal act.159 White collar offenders may rationalize
their behavior by asserting that no one will “really” be harmed.160 If an
act’s wrongfulness is partly a function of the harm it causes, an offender can
excuse or mollify his behavior if no clear harm exists.161 The classic use of
this technique in white collar crime is an embezzler describing his actions
as “borrowing” the money—by the offender’s estimation, no one will be
hurt because the money will be paid back.162 Offenders may also employ
this neutralization when the victim is insured or the harm is to the public or
market as a whole, such as in insider trading or antitrust cases.163 Although
seemingly available to him given his offense conduct, it does not appear
that Rajat Gupta neutralized his conduct by denying his acts caused
157. See Maruna & Copes, supra note 11, at 232 (describing how an engineer at B.F.
Goodrich failed to inform his supervisor of the reporting of false documents because he
“learned a long time ago not to worry about things over which [he has] no control”); see also
Benson, supra note 16, at 594 (reporting an income tax offender referring to criminal
behavior as “mistakes” resulting from ignorance or poor bookkeeping).
158. As the “master account,” the denial of responsibility neutralization necessarily
encompasses aspects of all neutralization techniques. For example, descriptions of the
defense of necessity neutralization in the white collar context are very similar to the denial of
responsibility neutralization. See COLEMAN, supra note 120, at 196–97 (describing different
versions of the defense of necessity technique).
159. Sykes & Matza, supra note 11, at 667.
160. Maruna & Copes, supra note 11, at 232.
161. See id.
162. See Cressey, supra note 19, at 15; Kieffer & Sloan, supra note 142, at 321–22.
163. See COLEMAN, supra note 120, at 196 (providing an example of a price fixing
offender asserting that while his conduct may have been “illegal,” it was not “criminal”
because “criminal action meant damaging someone, and we did not do that”); Benson, supra
note 16, at 598 (providing an example of a bank fraud offender arguing there was no harm
because “[t]he bank didn’t lose any money . . . . What I did was a technical violation.”
(second alteration in original)).
164. Why Gupta did not neutralize his conduct this way, even though it would seem
particularly appealing to do so given his offense, is an interesting question. It could be that
Gupta did neutralize his conduct by denying there was an identifiable victim, but he did not
make that known to the court. In other words, he may have made an after-the-fact decision
to hide his pre-act rationalization because he believed Judge Rakoff would reject it is as a
mitigating sentencing factor (and possibly even view it as an aggravator). On the other hand,
it could be that Gupta did not neutralize his conduct this way because he understands that
insider trading does cause injury to the market and other investors. Thus, the denial of injury
verbalization did not offer him a pre-act “defense” and would have had no neutralizing effect
to lessen the disconnect between his contemplated illegal behavior and his self-perception as
an upstanding citizen. This inquiry highlights some of the challenges in determining the
neutralizations that offenders employ, but also some of the benefits. If potential offenders
can be made aware that a neutralization is not valid, it ceases to be the critical component
Denial of the Victim. Even if a white collar offender accepts
responsibility for his conduct and acknowledges that his conduct is harmful,
he may insist that the injury was not wrong by denying the victim in order
to neutralize the “moral indignation of self and others.”165 Denying the
victim takes two forms. One is when the offender argues that the victim’s
actions were inappropriate and therefore he deserved the harm.166 The
offender claims rightful retaliation or punishment, and then denies the
victim aggrieved status.167 The second is when the victim is “absent,
unknown, or abstract,” which is often the case with property and economic
crimes.168 In this instance, the offender may be able to minimize his
internal culpability because there are no visible victims “stimulat[ing] the
offender’s conscience.”169
White collar offenders may use this
neutralization in frauds against the government, such as false claims or tax
evasion cases, and other crimes in which the true victim is abstract.170
Stanford appears to have rationalized his conduct by denying the victim.
He asserted that depositors knew the risks of investing and therefore were
not innocent victims, and that he was the true victim of the economic
Judge Hittner rejected both of Stanford’s proffered
Condemnation of the Condemners. White collar offenders may also
neutralize their behavior by shifting attention away from their conduct on to
the motives of other persons or groups, such as regulators, prosecutors, and
government agencies.171 By doing so, the offender “has changed the
subject of the conversation”; by attacking others, “the wrongfulness of his
own behavior is more easily repressed.”172 This neutralization technique
takes many forms in white collar cases: the offender calls his critics
hypocrites, argues they are compelled by personal spite, or asserts they are
motivated by political gain.173 The claim of selective enforcement or
prosecution is particularly prominent in this neutralization.174 In addition,
white collar offenders may point to a biased regulatory system or an
anticapitalist government.175 Stanford’s sentencing allocution provides a
study in the use of this neutralization technique. In his forty-minute speech,
allowing white collar crime to proceed. Put another way, by neutralizing the neutralizations,
crime can be prevented. See infra Part III.B.2.
165. Sykes & Matza, supra note 11, at 668.
166. Maruna & Copes, supra note 11, at 232.
167. See Kieffer & Sloan, supra note 142, at 322 (describing physicians committing
Medicare fraud as claiming the excess reimbursements they submitted were “only what they
rightfully deserved for their work”); Sykes & Matza, supra note 11, at 668 (“By a subtle
alchemy the delinquent moves himself into the position of an avenger and the victim is
transformed into the wrong-doer.”).
168. Maruna & Copes, supra note 11, at 233; Sykes & Matza, supra note 11, at 668.
169. Maruna & Copes, supra note 11, at 233.
170. Kieffer & Sloan, supra note 142, at 322.
171. Maruna & Copes, supra note 11, at 233; Sykes & Matza, supra note 11, at 668.
172. Sykes & Matza, supra note 11, at 668.
173. See Kieffer & Sloan, supra note 142, at 323.
174. See id.
175. See id.
[Vol. 82
Stanford attacked the government for causing his bank to fold, argued he
was being made a scapegoat for the financial collapse, and suggested his
prosecution was a result of his lack of political clout. The court summarily
rejected these rationalizations.
Appeal to Higher Loyalties. The appeal to higher loyalties neutralization
occurs when an individual sacrifices the normative demands of society for
that of a smaller group to which the offender belongs.176 The offender does
not necessarily reject the norms he is violating; rather, he sees other norms
that are aligned with his group as more compelling.177 In the white collar
context, the group could be familial, professional, or organizational.
Offenders rationalizing their behavior as necessary to provide for their
families, protect a boss or employee, shore up a failing business, or
maximize shareholder value are employing this neutralization technique.178
Notably, female white collar offenders have been found to appeal to higher
family loyalties more than their male counterparts.179 Both Gupta and
Madoff expressed higher loyalties when rationalizing their crimes. Gupta
suggested his long-time personal and business relationship with Rajaratnum
facilitated his behavior; Madoff suggested his brother’s domineering
relationship over him influenced his conduct. The judges in both cases
appeared to credit these rationalizations as mitigating sentencing factors.
Metaphor of the Ledger.
White collar offenders may accept
responsibility for their conduct and acknowledge the harm it caused, yet
still rationalize their behavior by comparing it to all previous good
behaviors.180 By creating a “behavior balance sheet,” the offender sees his
current negative actions as heavily outweighed by a lifetime of good deeds,
both personal and professional, which minimizes moral guilt.181 It seems
likely that white collar offenders employ this technique, or at least have it
available to them, as evidenced by current sentencing practices—almost
every white collar sentencing is preceded by a flood of letters to the court
supportive of the defendant and attesting to his good deeds.182 It appears
that Gupta and Madoff used this technique to rationalize their actions, and
176. Sykes & Matza, supra note 11, at 669.
177. See Maruna & Copes, supra note 11, at 233.
178. See Kieffer & Sloan, supra note 142, at 323 (describing an antitrust offender who
justified his conduct by saying, “I thought . . . we were more or less working on a survival
basis in order to try to make enough to keep our plant and our employees” (quoting JOHN E.
CONKLIN, CRIMINOLOGY 187 (8th ed. 2004))).
179. Compare Kathleen Daley, Gender and Varieties of White-Collar Crime, 27
CRIMINOLOGY 769 (1989) (finding female embezzlers were twice as likely to justify their
conduct based on family needs than male embezzlers), with Klenowski, supra note 145, at
233 (finding appeal to higher loyalties “with even greater frequency” for males than female
participants, calling the finding “one of the most salient discoveries” of his study).
797 (2005); Klenowski, supra note 145, at 54.
181. 2 SALINGER, supra note 180, at 797.
182. See, e.g., Ron Kampeas, Sharansky, 173 Others Plead Leniency for Libby,
JWEEKLY.COM (June 8, 2007), (describing the Scooter Libby sentencing, in which Libby
submitted 174 letters appealing for leniency when facing just a thirty-seven-month sentence).
Gupta, of course, submitted over 400 letters; Peter Madoff submitted sixty-three.
both of their judges found it compelling. However, Judge Hittner appeared
to reject Stanford’s attempts to rationalize his conduct based on a record of
business achievements alone.183
Claim of Entitlement. Under the claim of entitlement neutralization,
offenders rationalize their conduct on the grounds they deserve the fruits of
their illegal behavior.184 This neutralization is particularly common in
employee theft and embezzlement cases, but is also seen in public
corruption cases.185
Although he based it only on an “implicit
suggestion,”186 Judge Rakoff appears to have at least partially credited
Gupta’s rationalization that he earned the right to engage in unethical
behavior because he had cared for others for so many years.
Claim of Relative Acceptability/Normality. The final white collar
neutralization technique entails an offender justifying his conduct by
comparing it to the conduct of others. If “others are worse” or “everybody
else is doing it,” the offender, although acknowledging his conduct, is able
to minimize the attached moral stigma and view his behavior as aligned
with acceptable norms.187 In white collar cases, this neutralization
technique is often used by tax violators and in real estate and accounting
frauds.188 Both Madoff and Stanford implicitly rationalized their conduct
by comparing it to others. By referencing his brother’s fraud, Peter Madoff
drew a distinction between his relatively minor offenses and Bernie’s
massive Ponzi scheme. Stanford, on the other hand, seemed to be asserting
that his bank was doing nothing different than other international lenders.
Neither Judge Swain nor Judge Hittner found these rationalizations to be
mitigating sentencing factors.
The above discussion highlights a few additional points about
neutralization theory. First, although there seems to be a compulsion
among criminologists to categorize neutralization techniques (one this
Article indulges in), that there are differing types of neutralizations is not all
that remarkable. In fact, if it is true as some argue that rationalizing bad
behavior is “part of being human,”189 it follows that the list of
neutralization techniques will continue to grow as researchers study more
offenders in differing occupations. Put another way, “[w]hat is interesting
about neutralization theory is . . . what the neutralizations do,” and “not the
flavors it comes in.”190
183. This may suggest that different types of “credits” on the ledger carry different
weights with sentencers.
184. COLEMAN, supra note 120, at 198.
185. See id. (describing a former city councilman who explained his involvement in
corruption as due to his low salary and lack of staff); Klenowski, supra note 145, at 209–10.
186. Sentencing Memorandum and Order, supra note 2, at 12.
187. COLEMAN, supra note 120, at 197–98; Klenowski, supra note 145, at 67, 209–10.
188. See COLEMAN, supra note 120, at 197 (describing a real estate agent rationalizing
fraud as rampant); Benson, supra note 16, at 594 (describing tax offenders claiming that
“everybody cheats somehow on their taxes”).
189. Maruna & Copes, supra note 11, at 285 (quoting STANLEY COHEN, STATES OF
DENIAL 37 (2001)).
190. Id. at 284 (emphasis added).
[Vol. 82
That said, if there are demographic differences in the use of
neutralizations, that may provide insight into offenders’ differing selfnarratives and would be very valuable information.191 For example,
antitrust offenders neutralize their conduct differently than embezzlers.192
Women embezzlers neutralize their conduct differently than male
embezzlers.193 It is possible that women embezzlers of different ages,
races, and socioeconomic backgrounds neutralize their conduct differently.
A judge that understands the neutralization techniques employed by specific
types of white collar offenders would be a better-educated sentencer (and
arguably a more accurate one) in those cases. This highlights the need for
additional study of how and why white collar offenders neutralize their
Second, neutralizations are not “one size fits all.” Offenders employ
neutralizations in different degrees, combine them with other
neutralizations, and use them at different times. Moreover, the exact
verbalizations an offender uses to neutralize his behavior will be specific to
his circumstances, because they are part of his internal dialogue influenced
by his unique environment.195 The above list demonstrates that many of the
neutralization techniques partially overlap, and offenders may use multiple
techniques. For example, Madoff appears to have used at least four
neutralizations to minimize his guilt; Stanford may have used five or more.
Some of these are of the same category, but they are tailored to the
individual defendant. Thus, understanding offender behavior requires a
broad view of possible neutralizations, as well as a close view of the
offender’s specific conduct and circumstances.
Relatedly, the “toxicity” of neutralizations may vary.
neutralizations are sometimes described as being universally “bad” because
they facilitate criminal behavior, the issue is likely not so black and white.
It may be that neutralization techniques are arranged on a gradient, from
mostly benign to highly criminogenic.196 Some neutralizations appear to be
particularly offensive because they dehumanize victims or convert shame
into anger, both of which may suggest aggressive future offending.197
191. See id. (arguing that future research should investigate the nature of neutralizations
in contrasting situations, circumstances, contexts, and cultures). Michel Benson’s research
finding that white collar offenders use different neutralization techniques depending on the
type of offense committed is just this type of work. See Benson, supra note 16, at 591.
192. Benson, supra note 16, at 602–05.
193. Klenowski, supra note 145, at 233–35.
194. See Maruna & Copes, supra note 11, at 289–300 (listing areas of study for the “next
generation of neutralization research”).
195. See LANIER & HENRY, supra note 14, at 169–70.
196. See Maruna & Copes, supra note 11, at 290 (describing that the “working
assumption” in neutralization research is that all neutralizations are bad, but suggesting a
gradient from benign to “most toxic”).
197. See id. at 290. For example, the “denial of humanity” neutralization identified in the
context of the crime of genocide is seen as “the worst of the worst” because it promotes and
allows for further atrocities. Id.; see also Alexander Alvarez, Adjusting to Genocide: The
Techniques of Neutralization and the Holocaust, 21 SOC. SCI. HIST. 139, 166 (1997)
(studying the techniques of neutralization and the Holocaust).
Other neutralizations may be more innocuous, suggesting only episodic
offending and even allowing for eventual strengthened normative
behavior.198 This could explain why judges are willing to credit some
offender neutralizations as sentencing mitigators, but reject others and even
view them as aggravators. If, for example, the appeal to higher loyalties
neutralization is relatively benign, that could be why Judges Rakoff and
Swain viewed it as a mitigating explanation of Gupta’s and Madoff’s
conduct.199 Likewise, if condemning one’s condemners is more “toxic,”
that may explain why Judge Hittner rejected it in Stanford’s case. While an
in-depth exploration of this issue is outside this Article’s scope, the
possibility of a neutralizations gradient suggests that judges must not only
fully understand the underlying theory but also how specific offenders are
using neutralizations to facilitate their criminal conduct.200 It also suggests
a need for further research into the relative harmfulness of neutralizations
and if that corresponds with how judges credit or reject neutralizations at
Finally, there remains a nagging question concerning neutralizations:
how can researchers—and judges evaluating their theories—determine
whether an offender’s rationalizations are occurring prior to the criminal
act, making them true neutralizations, or after the act, rendering them mere
excuses?201 Although this question persists in the criminological literature,
it need not be answered directly because it creates a false dichotomy. As
explained by criminologists Shadd Maruna and Heith Copes, even if white
collar offenders commit criminal acts “in the absence of definitions
favorable to them” (i.e., without using verbalizations that minimize moral
guilt), those definitions “get applied retroactively to excuse or redefine the
initial deviant acts. To the extent that they successfully mitigate . . . selfpunishment, they become discriminative for repetition of the deviant acts
198. Maruna & Copes, supra note 11, at 290. Some argue that denying responsibility by
labeling oneself as an addict helps offenders by allowing them to see their past actions as
symptoms of a disease, rather than a lifelong character flaw, which reduces future offending.
Id. at 291. Critics contend that such labels “come[] at too high a cost” because they allow
for perpetual relapse into negative behavior patterns. Id.
199. An even more recent example of the appeal-to-higher-loyalties neutralization being
credited at sentencing is in the Kenneth Miller kidnapping case. Although Judge William
Sessions sentenced Miller, a Mennonite pastor, to twenty-seven months in prison for aiding a
born-again Christian woman in kidnapping her daughter from a former same-sex partner, the
judge said he admired Miller for the depth of his convictions. See Wilson Ring, Virginia
Pastor Credits ‘the Mercy of God’ in Custody Dispute at Sentencing,
Sessions then released Miller while his appeal was pending, despite Miller saying “he
couldn’t promise he would not again aid in international parental kidnapping.” Id.
200. Maruna and Copes suggest that the importance of neutralization theory is not
necessarily that neutralizations occur, or occur often, but that they occur in some instances to
allow for offending and not in others. They suggest that neutralizations may be thought of
not as direct causes of criminality, but as explanations of the persistence or desistence of
crime. Maruna & Copes, supra note 11, at 271. Under their view, whether certain
neutralization techniques allow for the persistence of crime more than others is an open
question that demands further research. Id. at 290.
201. See id. at 271 (calling this the “lingering ‘chicken-or-the-egg’ debate”).
[Vol. 82
and, hence, precede the future commission of the acts.”202 In other words, a
neutralization may start off as an after-the-fact rationalization, but
necessarily becomes the rationale that facilitates future offending.203
Because almost no white collar offenses are truly singular acts, but instead
are made up of a number of smaller acts occurring over time, there is little
concern that a defendant may be employing an after-the-fact rationalization
as an excuse that did not somehow neutralize his course of criminal
The preceding discussion demonstrates that a white collar defendant’s
sentence will likely be impacted by the court’s inquiry into what motivated
the defendant’s conduct. Judges appear to credit some rationalizations as
mitigators and deem others aggravators, all of which factors into the final
The court’s evaluation of a defendant’s rationalizations
necessarily confronts the neutralization techniques employed by that
defendant, techniques that have particular salience in white collar cases.
Yet the broad question posed at the outset of this Article remains: what
place, if any, does all of this have in white collar sentencing?
The answer requires a two-part analysis. The first addresses whether
judicial inquiry into offender neutralizations is consistent with current
sentencing doctrine. The Supreme Court’s recent decision in Pepper v.
United States,205 which reestablishes the importance of individualized
sentencing under the Sentencing Reform Act, indicates that it is. The
second part of the analysis addresses the more difficult normative question
of whether judicial inquiry into offender neutralizations is appropriate.
While there are significant potential drawbacks, neutralization inquiries
increase individualized sentencing and even, counterintuitively, provide
opportunities to disrupt white collar crime—benefits that weigh in favor of
the practice.
60 (3d ed. 1985)).
203. Id.; see also supra note 15.
204. That said, human thinking is undoubtedly complex; pinpointing precisely when a
thought enters a person’s mind and whether it changes over time is difficult, if not
impossible. Therefore, this “sequencing” question will likely remain open for some time.
Compare Robert Agnew, The Techniques of Neutralization and Violence, 32 CRIMINOLOGY
555 (1994) (engaging in a longitudinal study supporting neutralization theory’s sequencing),
with Paul Cromwell & Quint Thurman, The Devil Made Me Do It: Use of Neutralizations by
Shoplifters, 24 DEVIANT BEHAV. 535 (2003) (“No one . . . has yet been able to empirically
verify the existence of preevent [as opposed to postevent] neutralizations . . . .”).
205. 131 S. Ct. 1229 (2011).
A. Legal Justification for Judicial Inquiry into Offender Neutralizations
The Supreme Court’s Pepper opinion provides a strong jurisprudential
justification for judges inquiring into offender neutralizations. Before
discussing Pepper in detail, however, it is necessary to understand the
evolution of white collar sentencing.
1. Evolution of White Collar Sentencing
For the twenty years prior to 2005, federal sentences were determined
almost exclusively by the U.S. Sentencing Guidelines.206 Promulgated
under the authority of the Sentencing Reform Act of 1984,207 the
Guidelines had the goal of creating honesty in sentencing and reducing
unwarranted sentencing disparities prevalent in the indeterminate, parolebased scheme operating at the time.208 The Guidelines replaced the
indeterminate system with one in which judicial sentencing discretion was
significantly reduced by establishing narrow sentencing ranges based on a
series of factors, including the type of offense, adjustments related to
characteristics of the victim and offender, and the defendant’s criminal
From their inception, the Guidelines were heavily criticized. One of the
primary arguments against the Guidelines was that they were too rigid.210
Part of that rigidity came from the Guidelines’ sharp limitations on the
factors judges could consider at sentencing. Dozens of Guidelines
provisions directed judges to consider a range of aggravating factors, but to
ignore many in mitigation.211 While departures outside the calculated
sentencing range were contemplated by the Guidelines, they were only
allowed when the circumstances of a case were not adequately taken into
consideration by the Guidelines (i.e., when the case was outside the
206. See Bowman, supra note 4, at 379–80.
207. Pub. L. No. 98-473, 98 Stat. 1837 (codified in scattered sections of 18 and 28
COURTS 38–77 (1998) (providing a comprehensive history of federal sentencing); Paul J.
Hofer & Mark H. Allenbaugh, The Reason Behind the Rules: Finding and Using the
Philosophy of the Federal Sentencing Guidelines, 40 AM. CRIM. L. REV. 19, 20 (2003).
209. See U.S. SENTENCING COMM’N, supra note 208, § 1B1.1, at 16; Stephen Breyer, The
Federal Sentencing Guidelines and the Key Compromises Upon Which They Rest, 17
HOFSTRA L. REV. 1, 6–8 (1988).
210. J.C. Oleson, Blowing Out All the Candles: A Few Thoughts on the Twenty-Fifth
Birthday of the Sentencing Reform Act of 1984, 45 U. RICH. L. REV. 693, 723–28 (2011).
211. See, e.g., U.S. SENTENCING COMM’N, supra note 208, §§ 5H1.2, at 445, 5H1.4–.6, at
446–47, 5H1.10–.12, at 449 (explaining specific offender characteristics not ordinarily
relevant in sentencing); see also Stephen Breyer, Federal Sentencing Guidelines Revisited,
11 FED. SENT’G REP. 180, 183–84 (1999) (explaining that compromises by the Sentencing
Commission resulted in leaving out mitigating personal characteristics of the defendant in
favor of using criminal history to increase sentences).
[Vol. 82
“heartland” of typical cases).212 Departures were rarely granted, and when
they did begin to increase, Congress attempted to limit their use.213
Another criticism of the Guidelines was that they were too harsh.214
Particularly as to white collar offenders, the Guidelines operated as a oneway “upward ratchet,” continually driving sentencing ranges higher.215
Indeed, one of the compromises “embodied in the Guidelines” concerned
increased penalties for white collar defendants.216 Between 1987 and 2001,
sentencing ranges climbed from those initially elevated levels, as the “loss
table,” the main determiner of offense level for white collar crimes, was
repeatedly adjusted upward.217 A series of aggravating specific offense
characteristics was also added to the economic crime guidelines, which
increased sentencing ranges even more.218 This trend continued in the early
2000s, as Congress, through its Sarbanes-Oxley legislation, directed
heightened penalties for economic crimes in the wake of the Enron,
WorldCom, and Tyco corporate scandals.219 The result was a set of
guidelines for white collar offenders that limited probation, increased
average sentences, and exposed high-loss defendants to decades of
212. Koon v. United States, 518 U.S. 81, 96 (1996); U.S. SENTENCING COMM’N, supra
note 208, § 5K2.0(a)(4), at 452–56.
213. See Oleson, supra note 210, at 713, 724 (“At one point, House Majority Whip Tom
DeLay threatened, “‘The judges need to be intimidated. . . . They need to uphold the
Constitution.’ If they don’t behave, ‘we’re going to go after them in a big way.’” And in
what sometimes seemed like a battle between branches of government, some legislators
threatened to strip judges of all discretion, enacting broad slates of mandatory minimums.”
(quoting Joan Bikuspic, Hill Republicans Target ‘Judicial Activism’; Conservatives Block
Nominees, Threaten Impeachment and Term Limits, WASH. POST, Sept. 14, 1997, at A1)).
214. Id. at 707–14.
215. See James E. Felman, The Need To Reform the Federal Sentencing Guidelines for
High-Loss Economic Crimes, 23 FED. SENT’G REP. 138, 138 (2010).
216. See Breyer, supra note 209, at 18, 20; Alan Ellis et al., At a “Loss” for Justice,
CRIM. JUST., Winter 2011, at 34, 36. While the sentencing ranges for most crimes were
determined by analyzing pre-Guidelines sentences and then establishing sentencing ranges
based on past practices, the sentencing ranges for economic crimes were set higher than in
the past based on policy decisions made by the Sentencing Commission. See U.S.
SENTENCING COMM’N, supra note 208, at 4–5.
217. See Ellis et al., supra note 216, at 36. The loss table increases the offense level as
the loss to the victim increases. The current table has fifteen two-level increases, up to thirty
offense levels for a loss of more than $400 million. Each increase of six offense levels
approximately doubles the sentence. See U.S. SENTENCING COMM’N, supra note 208,
§ 2B1.1(b)(1), at 79.
218. See Bowman, supra note 4, at 387–91.
219. See id. at 432–35.
220. See Frank O. Bowman III, Sentencing High-Loss Corporate Insider Frauds After
Booker, 20 FED. SENT’G REP. 167, 168–69 (2008) (charting increases to a hypothetical
corporate defendant’s sentence from 1987 to 2007). These increases continue today. In a
series of amendments taking effect in November 1, 2012, the Commission increased
penalties for “organized” insider trading offenses and added an upward departure provision
for offenses that risk a significant disruption of a national financial market. See U.S.
id. at 5 (adding departure language applicable when the cumulative impact of the loss table
and the victims table overstates the seriousness of an offense). However, the Commission
has recently considered proposals by the American Bar Association that would likely reduce
Then, in 2004, the entire landscape shifted. In Blakely v. Washington, the
Supreme Court found that any sentencing increase based on judge-found
facts that took a sentence beyond the presumptive guideline range violated
the Sixth Amendment.221 The Court held that any fact, other than a prior
conviction, that raises the penalty “beyond the prescribed statutory
maximum must be submitted to a jury, and proved beyond a reasonable
doubt.”222 A year later, in United States v. Booker, the Court found that the
Sentencing Guidelines also violated the Sixth Amendment.223 Because the
Guidelines were mandatory, thereby requiring judges to increase a
defendant’s “statutory maximum for Apprendi purposes” based on factual
findings not submitted to a jury, they were unconstitutional.224 The Court
remedied this infirmity by excising two provisions of the Sentencing
Reform Act, thereby rendering the Guidelines advisory.225
Suffice it to say, the Booker decision drastically altered federal
sentencing. Instead of simply following the mandatory Guidelines, under
Booker, district judges must now follow a three-step process when
sentencing a defendant.226 First, the judge must calculate the applicable
Guidelines range.227 Then, the judge must determine whether to depart
from the sentencing range in situations falling outside the “heartland” of
cases to which the Guidelines were intended to apply.228 Third, after the
sentences for many economic crime offenders. See A REPORT ON BEHALF OF THE AMERICAN
CRIMES, available at
(proposing to restructure the fraud guideline to reduce reliance on loss and incorporate more
individual culpability factors).
221. Blakely v. Washington, 542 U.S. 296, 313–14 (2004). The decision in Blakely was
an extension of principles set forth in Apprendi v. New Jersey, 530 U.S. 466, 490 (2000).
declared unconstitutional a New Jersey hate crime enhancement that enabled a
sentencing judge to impose a sentence higher than the otherwise available statutory
maximum for various crimes based on a finding by a preponderance of the
evidence that an offense involved racial animus. The Apprendi Court asserted the
hate crime sentencing enhancement was constitutionally problematic because,
“[o]ther than the fact of a prior conviction, any fact that increases the penalty for a
crime beyond the prescribed statutory maximum must be submitted to a jury, and
proved beyond a reasonable doubt.”
Douglas A. Berman, Foreword: Beyond Blakely and Booker: Pondering Modern
Sentencing Process, 95 J. CRIM. L. & CRIMINOLOGY 653, 672 (2005) (alteration in original)
(quoting Apprendi, 530 U.S. at 490).
222. See Blakely, 542 U.S. at 301.
223. United States v. Booker, 543 U.S. 220, 226–27 (2005).
224. Id. at 232 (internal quotation marks omitted).
225. See id. at 245. Because the now advisory Guidelines did not create “statutory
maximums” under Apprendi and Blakely, no Sixth Amendment concerns were implicated.
See id. at 264–65. Thus, the Court remedied the constitutional infirmities of the Guidelines
without completely destroying the federal sentencing scheme that had been in place for the
past twenty years.
226. See Rita v. United States, 551 U.S. 338, 351 (2007) (setting out the three-step
227. See id.; Gall v. United States, 552 U.S. 38, 49 (2007) (“The Guidelines should be the
starting point and the initial benchmark [at sentencing].”).
228. Rita, 551 U.S. at 351.
[Vol. 82
sentencing range is calculated, the judge must then consider “all of the
[Sentencing Reform Act’s] § 3553(a) factors to determine whether they
support the sentence requested.”229 It is here that a judge is free to provide
a “variance” if she decides an outside-Guidelines sentence is warranted.230
2. Pepper’s Impact on White Collar Sentencing
While Blakely and Booker recrafted federal sentencing into an advisory
guidelines system, not until Pepper did the Court unequivocally establish
the breadth of district courts’ sentencing discretion.231 This wide discretion
allows courts to inquire into defendants’ neutralizations at sentencing.
In Pepper, the issue before the Court was whether a district court could
consider evidence of a defendant’s postsentencing rehabilitation at
resentencing.232 Jason Pepper had originally been sentenced, pursuant to a
large downward departure under the Guidelines, to twenty-four months’
imprisonment for conspiracy to distribute methamphetamine.233 The
government appealed, arguing the departure was too great.234 After a
Booker remand,235 the district court resentenced Pepper to the original
sentence, this time based partly on his postsentencing rehabilitation, which
included successful drug treatment, a straight-A performance as a full-time
college student, steady employment, and strong family support.236 The
government appealed again. The Eighth Circuit determined that “evidence
of postsentencing rehabilitation ‘is not relevant and will not be permitted at
resentencing,’” and the case was once again remanded.237 Without the
benefit of his postsentencing rehabilitation arguments, Pepper was
resentenced to sixty-five months’ imprisonment.238 Pepper appealed again;
this time the Eighth Circuit sustained the sentence.239
229. Gall, 552 U.S. at 49–50.
230. Id. at 50.
231. See Pepper v. United States, 131 S. Ct. 1229, 1235 (2011).
232. See id. at 1235–36.
233. See id. at 236.
234. See id.
235. Booker remands occurred in cases that were pending when the Booker decision was
decided, necessitating a remand to determine if the court had enhanced the applicable
sentence through judge-found facts not agreed to by the parties. See, e.g., United States v.
Goldberg, 406 F.3d 891, 892, 894 (7th Cir. 2005) (discussing procedures and pitfalls under
Booker remands).
236. Pepper, 131 S. Ct. at 1236–37.
237. Id. at 1237 (quoting United States v. Pepper, 486 F.3d 408, 413 (8th Cir. 2007))
(stating that a policy statement in the Guidelines against considering postsentencing
rehabilitation, § 5K2.19 (“Post-Sentencing Rehabilitative Efforts”), formed the basis of the
Eighth Circuit’s decision).
238. Id. at 1238. Because he had already served his original twenty-four-month sentence,
Pepper would have had to surrender to the Bureau of Prisons for an additional forty-one
months, likely losing his job and apartment in the process.
239. Id. Pepper had an intervening trip up to the Eighth Circuit and back down for
resentencing; all told, the case was before the Eighth Circuit four times and the Supreme
Court twice. Id. at 1238–39.
Justice Sotomayor, writing for the majority, overturned the Eighth
Circuit’s decision. The Court’s opinion began by recognizing the right of
each defendant to be sentenced individually:
It has been uniform and constant in the federal judicial tradition for the
sentencing judge to consider every convicted person as an individual and
every case as a unique study in the human failings that sometimes
mitigate, sometimes magnify, the crime and the punishment to ensue. 240
The Court said it was “‘essential’”241 that the district court “consider the
widest possible breadth of information about a defendant” to ensure that the
sentence “‘will suit not merely the offense but the individual.’”242
The Court found that the language of the Sentencing Reform Act
surviving after Booker did not constrain judicial sentencing discretion;
indeed, it “preserved the traditional discretion of sentencing courts to
‘conduct an inquiry broad in scope, largely unlimited’” in the kind of
information that may be considered.243
In determining the sentence to impose within the guideline range, or
whether a departure from the guidelines is warranted, the court may
consider, without limitation, any information concerning the background,
character and conduct of the defendant, unless otherwise prohibited by
The Court therefore held that a district court may consider a defendant’s
postsentencing rehabilitation at resentencing and grant a downward
variance when appropriate as part of the court’s consideration of the
Sentencing Reform Act’s § 3553(a) factors.245 Because this conclusion
conflicted with a statutory provision that precluded a court on resentencing
from “imposing a sentence outside the Guidelines range except upon a
‘ground of departure’ that was expressly relied upon in the prior
sentencing,”246 the Court invalidated the provision as inconsistent with
Pepper provides strong doctrinal support for judicial inquiry into
offender neutralizations. Most fundamentally, as the Booker-throughPepper line of cases explains, courts now have almost unrestrained
discretion to impose a sentence. This means there is no more forced
“rigidity” in sentencing. Pepper reconfirms that Booker eliminated the
required adherence to the Guidelines and their proscription on considering
certain offender characteristics.248 Pursuant to Booker, strict adherence to
the Guidelines was replaced with discretion bounded only by the broad
Id. at 1239–40 (citation omitted).
Id. at 1240 (quoting Williams v. New York, 337 U.S. 241, 247 (1949)).
Id. (quoting Wasman v. United States, 468 U.S. 559, 564 (1984)).
Id. (quoting United States v. Tucker, 404 U.S. 443, 446 (1972)).
Id. (quoting U.S. SENTENCING GUIDELINES MANUAL § 1B1.4 (2010)).
See id. at 1246.
Id. at 1243.
Id. at 1247, 1249.
Id. at 1241–42, 1247.
[Vol. 82
statutory sentencing factors underlying the Sentencing Reform Act.249 And
that language, contained in § 3553(a), makes clear that judges are permitted
to consider defendants’ neutralizations.
Section 3553(a) begins with an overarching mandate: “[C]ourt[s] shall
impose a sentence sufficient, but not greater than necessary, to comply with
the purposes [of the statute].”250 The statute goes on to direct courts to
consider almost anything related to the defendant or his potential
The court, in determining the particular sentence to be imposed, shall
(1) the nature and circumstances of the offense and the history and
characteristics of the defendant;
(2) the need for the sentence imposed—
(A) to reflect the seriousness of the offense, to promote respect
for the law, and to provide just punishment for the offense;
(B) to afford adequate deterrence to criminal conduct;
(C) to protect the public from further crimes of the defendant;
(D) to provide the defendant with needed educational or
vocational training, medical care, or other correctional
treatment in the most effective manner;
(3) the kinds of sentences available;
(4) the kinds of sentence and the [Guidelines] sentencing range . . .
(5) any pertinent policy statement [contained in the Guidelines] . . .
(6) the need to avoid unwarranted sentence disparities . . . ; and
(7) the need to provide restitution to any victims of the offense.251
In addition, a companion provision states that, “[n]o limitation shall be
placed on the information concerning the background, character, and
conduct of a person convicted of an offense which a court of the United
States may receive and consider for the purpose of imposing an appropriate
sentence.”252 Accordingly, courts have essentially “no boundaries” under
current federal law that would constrain their inquiries at sentencing,
249. See Amy Baron-Evans, Rita, Gall and Kimbrough: A Chance for Real Sentencing
Improvements (2008) (unpublished manuscript), available at
250. 18 U.S.C. § 3553(a) (2012). This provision embodies the “parsimony principle,”
which has been described as requiring “a sentencing court when handing down a sentence
[to] be stingy enough to avoid one that is too long, but also that it be generous enough to
avoid one that is too short.” United States v. Irey, 612 F.3d 1160, 1197 (11th Cir. 2010); see
also Nancy Gertner, Federal Sentencing Guidelines: A View from the Bench, 29 HUM. RTS.
6, 6 (2002).
251. 18 U.S.C. § 3553(a) (emphasis added).
252. Id. § 3661.
including inquiries into the neutralization techniques defendants may be
Indeed, the “shall consider” language of § 3553(a) suggests courts are
compelled to consider defendants’ motivations, which necessarily include
the neutralizations employed. How a defendant neutralizes his criminal
behavior so that it may proceed touches on at least three of § 3553(a)’s
factors. The type of neutralization a defendant employs is part of the nature
and circumstances of the offense and the history and characteristics of the
defendant—it is the psychological mechanism that makes the offense
possible.254 A defendant’s use of neutralizations also impacts the need for
the sentence imposed, particularly when courts are considering the four
traditional purposes of punishment outlined in the statute.255 Finally, if
some judges are inquiring into offender neutralizations and factoring them
in to sentencing determinations (which the Gupta, Madoff, and Stanford
cases demonstrate they are), the need to avoid unwarranted sentence
disparities consideration is also implicated.
Pepper supports judicial inquiry into offender neutralizations in another,
less direct way. Pepper’s holding has the practical effect of refocusing
sentencing on the § 3553(a) factors, but the normative basis of the Court’s
opinion is also important. Justice Sotomayor began her analysis by
recognizing the traditional right of each defendant to be sentenced as an
individual.256 Underlying this tradition, she found, was the principle that
punishment should be tailored to the offender, not just the crime. 257 This
principle, which “justice generally requires,” stems directly from the
Court’s prior rejection of determinate sentencing schemes and is consistent
with the now widely accepted view of sentencing as being “most just” when
it contemplates both the offense and the offender.258 This requires judges
253. See Sean D. O’Brien, When Life Depends on It: Supplementary Guidelines for the
Mitigation Function of Defense Teams in Death Penalty Cases, 36 HOFSTRA L. REV. 693,
713 (2008) (“[T]he scope of mitigation evidence [is] ‘potentially infinite’ and . . . ‘anything
under the sun’ can be tendered by the defense in mitigation of punishment” (quoting Ayres
v. Belmontes, 549 U.S. 7, 21 (2006); Lockett v. Ohio, 438 U.S. 586, 631 (1978) (Rehnquist,
J., concurring in part and dissenting in part))). Of course, there are bounds to what evidence
an advocate may introduce at a sentencing hearing. See FED. R. CRIM. P. 32(i)(2).
254. See Sykes & Matza, supra note 11, at 667.
255. See 18 U.S.C. § 3553(a)(2)(A)–(D); see also infra Part III.B.1.
256. Pepper v. United States, 131 S. Ct. 1229, 1239–40 (2011).
257. Id. at 1240. The Court cited Williams v. New York, 337 U.S. 241, 246 (1949), which
relied on a number of social science texts extolling the virtues of individualized sentencing.
See, e.g., Sheldon Glueck, Principles of a Rational Penal Code, 41 HARV. L. REV. 453, 463–
64 (1928) (“In a word, individualization is necessary on the part of the court and other
institutions dealing with the offender; and effective individualization is not based on
guesswork, mechanical routine, ‘hunches,’ political considerations, or even (as so many
judges seem to think) on past criminal record alone. It must rest on a scientific recognition
and evaluation of those mental and social factors involved in the criminal situation which
make each crime a unique event and each criminal a unique personality.”).
258. Pepper, 131 S. Ct. at 1240. But see id. at 1252 (Breyer, J., concurring) (contending
that individualized sentencing is not the only relevant tradition: “A just legal system seeks
not only to treat different cases differently but also to treat like cases alike. Fairness requires
sentencing uniformity as well as efforts to recognize relevant sentencing differences.”).
[Vol. 82
to consider, “without limitation,”259 any mitigating or aggravating evidence
concerning the defendant in order to achieve a sentence “sufficient, but not
greater than necessary.”260 Evidence of how and why a defendant
neutralizes his behavior, which allows the criminal conduct to occur, is
important to the individualized sentencing process Pepper envisions.
B. Normative Justification for Judicial Inquiry
into Offender Neutralizations
While judicial inquiry into offender neutralizations is legally permissible,
and likely compelled, under current sentencing law, whether it is
normatively appropriate is a separate question. The practice raises a
number of potential positives and negatives. Ultimately, the benefits of
increased individualized sentencing and opportunities to disrupt the
mechanisms of white collar crime outweigh the possible negatives
associated with the practice.
1. Increased Individualized Sentencing
The most direct benefit of judges inquiring into how defendants
neutralize their conduct is the one just discussed: increased individualized
sentencing. Pepper reestablishes that individualized sentencing is the most
just way to impose punishment—that a fair sentence considers both the
offense and the offender.261 At the same time, criminological theory
explains that neutralizations are an integral component of both white collar
offenses and the offenders who commit them.
The verbalizations that a defendant uses to neutralize his antinormative
behavior and bring it in line with society are one of the three causal
elements of any white collar crime;262 therefore, neutralizations are
fundamental to white collar offenses.263 While neutralizations are not
explicit offense elements, they facilitate the commission of white collar
crime and are intrinsic to it.264 Yet, as discussed above, specific
neutralization techniques may vary by offense type.265 In order to fully
understand the offense committed, a judge must understand the
neutralizations that preceded it.
Neutralizations are also critical to understanding the offender.
Neutralizations explain the psychological processes an offender undergoes
in order to commit the offense—they are part of the explanation of how the
259. Id. at 1240.
260. 18 U.S.C. § 3553(a).
261. Pepper, 131 S. Ct. at 1239–40.
262. Sykes & Matza, supra note 11, at 667.
263. Cressey, supra note 19, at 15.
264. Some white collar criminal statutes do make defendants’ motivations, and therefore
their rationalizations and neutralizations, more explicitly part of the offense elements. See
Hessick, supra note 19, at 96–97 (describing how obstruction of justice and bribery offenses
contain elements requiring the defendant to act with corrupt or improper purposes,
necessarily requiring an evaluation of the defendant’s reasons for acting).
265. See Benson, supra note 16, at 605; Klenowski, supra note 145, at 233.
offender “bec[ame] delinquent.”266 In this way, neutralizations are like any
other demographic or social history factor considered by a sentencer. Of
course, not all offenders will employ the same neutralization techniques.
Despite all being high-profile white collar defendants, Gupta, Madoff, and
Stanford neutralized their criminal conduct much differently—the
techniques used were unique to each offender’s background and character,
influenced by their personal and professional environment.267 It follows
that a judge inquiring into a defendant’s neutralizations will be better
educated as to the “unique . . . human failings that sometimes mitigate,
sometimes magnify, the crime and the punishment.”268
Neutralization inquiries also aid individualized sentencing determinations
by informing judges as to the retributive and utilitarian purposes of
punishment.269 Judges focused on retributive punishment goals are
generally trying to evaluate the harm caused by the offense and assign it
some proportional weight, thereby punishing the offender based on his
relative blameworthiness.270 Neutralization inquiries in white collar cases
can help judges make this type of assessment. When a judge understands
the motivations of an offender and the specific neutralization techniques
used to facilitate the crime, relative blameworthiness comes into sharper
focus. A company executive who illegally backdates stock options by
convincing himself that he deserves a little extra for all his hard work
(claim of entitlement), and that the shareholders should not care anyway
because of all the money he has made them (denial of the victim), is more
blameworthy than an executive who commits an accounting or bank fraud
to secure a loan to keep a failing company afloat and its personnel
266. Sykes & Matza, supra note 11, at 667.
267. See LANIER & HENRY, supra note 14, at 169–70. For example, Peter Madoff
attempted to neutralize his conduct through the claim-of-relative-acceptability technique,
which was tailored to his brother’s conduct and their professional environment. See
Transcript of Sentencing Hearing, supra note 71, at 28; see also Sentencing Memorandum,
supra note 71, at 20–23. Stanford employed a similar technique, but the focus was different
because he saw himself operating in the global banking environment. See Transcript of
Sentencing Proceedings, supra note 97, at 32, 37.
268. Pepper, 131 S. Ct. at 1240 (quoting Koon v. United States, 518 U.S. 81, 113 (1996)).
WORKABLE SYSTEM 7–9 (2013) (providing an overview of sentencing principles). Judges
are required to consider these punishment purposes at sentencing under 18 U.S.C.
§ 3553(a)(2).
Hessick, supra note 19, at 113. For example, a retributivist judge would deem a defendant
who committed murder as more deserving of punishment than a thief because the murderer
caused more relative harm. And most judges, also consistent with retributivism, would deem
a mercy killer less blameworthy than a contract killer. While both murderers have inflicted
the same relative harm—the taking of another’s life—we see the contract killer as more
culpable, and thus deserving of more punishment, because he acted for profit rather than to
end suffering. See id. at 114; Dan M. Kahan, What Do Alternative Sanctions Mean?, 63 U.
CHI. L. REV. 591, 603 (1996). This can best be understood through the expressivism strain
of retributivism, which contends that an “individual deserves punishment when she commits
an illegal act, because in committing that act, the individual has demonstrated that she does
not respect an important value, such as a victim’s moral worth.” See Hessick, supra note 19,
at 113.
[Vol. 82
employed (appeal to higher loyalties). Both crimes may result in similar
financial harm, but we view the offenders’ relative culpability
differently.271 Judicial inquiry into an offender’s specific neutralizations
helps clarify relative blameworthiness and facilitates proportional
Courts evaluating offender neutralizations will also have more insight
when considering utilitarian punishment goals. Although judges are
required to consider deterrence, incapacitation, and rehabilitation when
sentencing,272 in white collar cases general deterrence is usually the
primary focus.273 General deterrence is the idea that the threat of
punishment to one offender will result in lawful behavior of other potential
offenders.274 The problem with basing punishment on this notion is that
there are no reliable findings related to the marginal deterrent effects of
various punishment levels.275 General deterrence is premised on the
potential offender’s knowledge of the penalty and risk of detection, and this
type of “factual data on which a deterrent system must be founded do[es]
not exist.”276
This does not mean that general deterrence is an invalid sentencing
consideration in white collar cases.277 But, judges should consider the
concept differently in light of neutralization theory. As will be discussed in
the next section, if neutralizations allow individuals to construct selfnarratives enabling the commission of white collar crime, helping those
individuals and other potential offenders understand that mental process can
break the causal chain—neutralizations can be neutralized.278 In other
271. See United States v. Ranum, 353 F. Supp. 2d 984, 990 (E.D. Wis. 2005); Podgor,
supra note 19, at 747–48 (discussing the relative moral culpability of a white collar
defendant not acting for personal gain).
272. See 18 U.S.C. § 3553(a)(2)(B)–(D) (2012).
273. That is because judges understand that upon conviction most white collar offenders
lose their jobs, professional licenses, and status in the community. See Kenneth Mann et al.,
Sentencing the White-Collar Offender, 17 AM. CRIM. L. REV. 479, 483–84 (1980); Podgor,
supra note 19, at 753. Therefore, it is highly unlikely they will reoffend, which is the
concern that primarily drives the need to specifically deter, incapacitate, or rehabilitate an
274. See ASHWORTH, supra note 270, at 64 (discussing general and specific deterrence).
275. See Hessick, supra note 19, at 116.
276. ASHWORTH, supra note 270, at 64.
277. Indeed, Carissa Hessick makes a compelling argument for expanding motive’s role
in punishment to deter more crime. See Hessick, supra note 19, at 116–18.
278. Under Cressey’s theory, eliminating any of the three causal elements of white collar
crime—nonshareable financial problem, position of trust, or verbalizations—would reduce
recidivism. See Cressey, supra note 19, at 14. However, Cressey believed only two elements
could be “effectively blocked” to impede white collar crime. Id. at 15. He argued that
companies, through workplace education and counseling, could reduce the number of
employees possessing nonshareable financial problems. See id. He viewed this as a frontend crime prevention issue, not necessarily a treatment issue. He did not believe the
position-of-trust element could be addressed because of the prevalence and necessity of trust
in the workplace. CRESSEY, supra note 117, at 154–55. He viewed the elimination of
verbalizations as the most appropriate target for rehabilitative penal programs. See id. at 155.
He cautioned, however, that prison environments could cause offenders to replace one set of
neutralizations with another. See id. at 156. Other researchers are less pessimistic than
words, judges may be able to deter future white collar crime not simply
through punishment, but by educating potential offenders as to the
psychological mechanisms that allow for the commission of crime.
The practice of judges inquiring into offender neutralizations raises a
host of additional positives and negatives. One positive might be that
judges will use these inquiries to mitigate against what many consider to be
an overly harsh sentencing scheme for white collar offenders. As explained
above, although Booker rendered the Sentencing Guidelines advisory, they
are still the “initial benchmark” at sentencing and carry great weight in most
sentencing decisions.279 And because of steady increases in penalties for
economic crimes, white collar defendants, particularly those facing high
loss amounts, are being sentenced drastically higher than in the past.280
Judicial inquiry into a defendant’s neutralizations may provide the court
with a more complete understanding of the defendant’s conduct, possibly
mitigating his criminal behavior that would have otherwise resulted in a
lengthy sentence.
This appears to be precisely what happened in Judge Rakoff’s courtroom.
He rejected the Guidelines’ heavy reliance on the monetary gain to
Rajaratnum from Gupta’s inside tips because it failed to address what he
saw as the heart of Gupta’s crime—the abuse of trust.281 Judge Rakoff then
sought an explanation for that abuse of trust, finding credible Gupta’s
rationalizations of his conduct.
Gupta’s appeal-to-higher-loyalty,
metaphor-of-the-ledger, and claim-of-entitlement neutralizations became
sentencing mitigators under § 3553(a), resulting in a downward variance
from the applicable Guidelines range.282
Many, of course, would view what happened in Gupta’s case as a great
negative. They not only disagree that the economic crime guidelines are
overly harsh, but they argue white collar offenders are finally receiving
sentences commensurate with the harms they cause. Therefore, judicial
inquiry into offender neutralizations is not necessary, especially if they lead
Cressey. See Maruna & Copes, supra note 11, at 299–300 (describing programs successfully
challenging offenders’ neutralization techniques but acknowledging the effectiveness of
these programs “remains an [open] empirical question”).
279. See Gall v. United States, 552 U.S. 38, 49 (2007).
280. See White Collar Sentencing Data, supra note 26, at 129 (showing a steadily
increasing average sentence length for white collar offenders since 2005); see also Felman,
supra note 215, at 138. Some say, pointedly, that white collar sentencing, even under the
advisory Guidelines system, is completely “out of whack” and “patently absurd on [its]
face.” See Bowman, supra note 220, at 172; see also United States v. Adelson, 441 F. Supp.
2d 506, 515 (S.D.N.Y. 2006). As Professor Frank Bowman points out, “[U]nder the current
Guidelines, a judge who wanted to impose a 25-year sentence on an Ebbers, a Skilling, or a
Rigas, thus equating their economic offenses with murder by a five-time felon, would have
to depart downward 19 offense levels to do it.” Bowman, supra note 220, at 169.
281. Sentencing Memorandum and Order, supra note 2, at 2.
282. It appears that many judges sentencing white collar offenders are finding reasons to
impose lower prison terms than suggested by the applicable Guidelines range, particularly in
high-loss cases that go to trial. See White Collar Sentencing Data, supra note 26, at 131
(reporting judges are varying downward in 23.5 percent of white collar cases that end in a
guilty plea and in 43.7 percent that end in a conviction after trial).
[Vol. 82
to more lenient sentences.283 Moreover, critics might argue that judicial
inquiry into the mental processes that white collar offenders undergo may
create other problems. It is possible that neutralizations could become
legally sanctioned proxies for judges wishing to give lenient sentences to
offenders with which they most closely identify. This was one of the
concerns expressed at the time of the Sentencing Reform Act’s passage and
embodied in the original fraud guideline.284 The metaphor-of-the-ledger
neutralization, which Judges Rakoff and Swain credited, seems particularly
susceptible to becoming a tool for judges seeking to lessen punishment for
defendants with similar backgrounds as their own.285
All of this highlights the larger concern of increasing sentencing
disparity. Inherently, the more individualized sentencing becomes, the less
uniformity exists. Creating uniformity in sentencing was one of the
primary goals of the Sentencing Reform Act.286 While the Booker-throughPepper line of cases preferences judicial sentencing discretion over
mandatory guidelines that guarantee uniformity, a “just legal system seeks
not only to treat different cases differently but also to treat like cases
alike.”287 And for white collar sentences, disparity is on the rise. Nongovernment sponsored below Guidelines range sentences (i.e., sentences in
which there was a judicial departure or variance without a government
motion) in fraud cases, which include white collar offenses,288 rose from
6.2 percent prior to Booker, to 16.4 percent after Booker, and now sits at
23.8 percent.289 The limited data available focusing specifically on white
collar offenders indicates that non-government sponsored below range
283. See, e.g., Andrew Weissmann & Joshua A. Block, White-Collar Defendants and
White-Collar Crimes, 116 YALE L.J. POCKET PART 286 (2007) (disagreeing that white collar
defendants are subjected to uniquely harsh penalties under the Guidelines).
284. See Bowman, supra note 4, at 385; Breyer, supra note 209, at 20–21.
285. Of course, Judge Swain and Judge Hittner rejected many of the neutralizations
offered by Madoff and Stanford, so there are no guarantees as to how judges will view
specific offender neutralizations.
286. See U.S. SENTENCING COMM’N, supra note 208, at 3–4; Hofer & Allenbaugh, supra
note 208, at 20–21.
287. Pepper v. United States, 131 S. Ct. 1129, 1252 (2011) (Breyer, J., concurring).
288. The Sentencing Commission does not consistently break out statistics for white
collar offenses; the fraud offense category includes white collar crimes, as well as other
forms of economic crimes sentenced under § 2B1.1. See U.S. SENTENCING GUIDELINES
MANUAL § 2B1.1 (2013).
289. See Prepared Testimony of Judge Patti B. Saris, Chair, United States Sentencing
Commission, U.S. SENTENCING COMMISSION 47 (Oct. 12, 2011),
12_Saris_Testimony.pdf; 2012 Sourcebook of Federal Sentencing, U.S. SENTENCING
COMMISSION tbl.27A (2012),
_and_Sourcebooks/2012/sbtoc12.htm (last visited Apr. 26, 2014). The numbers are even
higher when focusing on offenders sentenced under the specific fraud guideline, § 2B1.1,
which would include the vast majority of white collar offenders. In fiscal year 2012, 25.3
percent of § 2B1.1 offenders received a non-government sponsored below range sentence.
Id. tbl.28. Non-government sponsored below range sentences are the best measure of
whether the Guidelines are being followed by sentencing courts because they represent
“pure” judicial discretion.
sentences currently top 25 percent.290 This trend appears to be even more
pronounced for high-loss economic crimes, such as those committed by
Gupta, Madoff, and Stanford. Whether these increases in variance rates are
warranted or not depends on one’s point of view, but providing judges with
another tool to vary from the Guidelines will likely decrease overall
sentencing uniformity.291
One final consideration related to increased individualized sentencing is
whether courts possess the institutional competency to accurately assess
offender neutralizations. Most district court judges are not social scientists
or criminologists. It could be argued that judges lacking criminological
training are ill equipped to investigate and accurately assess how offenders
neutralize their conduct. While there is some intuitive appeal to this
argument, sentencing judges routinely make assessments regarding
defendants’ backgrounds and mental processes, including delving into their
motivations. The nature of some offenses requires it,292 and § 3553(a)
suggests that such an inquiry is mandated in all cases. Not surprisingly,
then, many judges see these inquiries as their “prime objective” at
sentencing, using their considerable autodidactical abilities to perform them
effectively.293 Even if individual judges do not possess special training in
evaluating neutralizations, they are not acting alone during the sentencing
process. Each judge is aided by a comprehensive presentence investigation
report created by a probation officer who has special expertise in
uncovering all relevant information about the offender and the offense.294
This is not to mention the role of the prosecutor and defense attorney,
whose obligation it is to educate the court, possibly through expert
testimony, as to all sentencing aggravators and mitigators, including
offender neutralizations.295
290. See White Collar Sentencing Data, supra note 26, at 128.
291. Rising variance rates could be tempered by formalizing neutralization inquiries and
making their evaluation part of the Guidelines themselves. Neutralizations could be taken
into account by amending the text of the fraud guideline or its application notes, or by
adding a policy statement addressing neutralizations. Some may argue, however, that this
simply hides sentencing disparity; offenders are still being sentenced in a less uniform
manner, but the disparity is now sanctioned by the Guidelines.
292. See Hessick, supra note 19, at 96–97.
293. Irving R. Kaufman, Sentencing: The Judge’s Problem, ATL. MONTHLY, Jan. 1960,
at 3, available at
294. See generally OFFICE OF PROB. & PRETRIAL SERVS., supra note 25.
295. The adversarial process, which is still very active during sentencing, should guard
against defendants raising neutralizations as a way to game sentencings to get a lower
punishment. The validity of a defendant’s claimed pre-act mental process may be tested by
the usual evidence at sentencings—witness testimony, affidavits, documentary evidence, and
the like.
[Vol. 82
2. Disrupting the Mechanisms That Make White Collar Crime Possible
In addition to increased individualized sentencing, judicial inquiry into
offender neutralizations also has the benefit of disrupting the mechanisms
that make white collar crime possible. How this may occur, however, is
somewhat counterintuitive.
In one view, all neutralizations are negative because they are the
mechanisms by which individuals commit white collar crime. According to
Cressey, without neutralizations, there is no white collar crime.296
Therefore, it may seem that regardless of what the law allows, sentencing
judges should not be inquiring into or evaluating neutralizations because
that would only perpetuate their existence, thereby perpetuating the very
offenses judges are punishing.297 Under this view, any consideration by a
court of crediting an offender’s neutralization as a sentencing mitigator (as
occurred in the Gupta and Madoff cases) should be strictly prohibited.
Although this view has the benefit of definiteness, it is myopic.
Neutralizations originate from many different sources, not just the legal
system or sentencing hearings. Neutralization theory posits that offenders
learn the verbalizations they use to neutralize their criminal conduct from a
number of sources.298 While these sources may include the legal system
generally and judicial sentencing determinations specifically, they also
include the corporate and organizational environments in which offenders
work and live—a more direct (and likely) source of learned
neutralizations.299 Therefore, a blanket prohibition on judges inquiring into
neutralizations would not eliminate the mechanisms that make white collar
crime possible.300
A better approach allows judges to inquire into defendants’ motivations
and rationalizations, confront the neutralization techniques that are
revealed, and credit or reject those neutralizations as part of the court’s
discretionary sentencing process. By doing so, judges have an opportunity
to neutralize neutralizations.
If courts publically explain what
neutralizations are, how offenders use neutralizations to facilitate their
296. See Cressey, supra note 19, at 15 (“It follows from my generalization that
embezzling can be effectively blocked at the . . . verbalization point.”).
297. Indeed, Sykes and Matza believed the legal system itself provided many of the
neutralizations that offenders used to facilitate their delinquency. See MATZA, supra note
148, at 61 (“The law contains the seeds of its own neutralization.”); Sykes & Matza, supra
note 11, at 666.
298. See LANIER & HENRY, supra note 14, at 169–70; Benson, supra note 16, at 588.
299. See Benson, supra note 16, at 588 (explaining how neutralization techniques vary
across white collar offense types).
300. It could be argued that judges, as part of their sentencing determinations, should be
required to identify white collar neutralizations and then reject them, possibly even treating
any neutralization raised by a defendant as a sentencing aggravator. This practice might
lessen the effectiveness of neutralizations because judges would be rejecting their validity
directly. The problem with this approach is that it would still not capture neutralizations
learned from other sources outside of the legal or sentencing context, and it would likely
drive neutralizations underground. No defendant would offer a rationalization, no matter
how true, for fear of it being used as a sentencing aggravator. Neutralizations would
continue to enable white collar crime; they would simply be more difficult to identify.
crimes, and why neutralizations fail as true “defenses” to illegal behavior,
future potential offenders may view neutralizations differently. Put another
way, a neutralization that is a demonstrated failure in harmonizing a white
collar offender’s breach of trust and his self-perception as an upstanding
citizen ceases to adequately rationalize the illegal behavior. And when a
neutralization ceases to rationalize illegal behavior, the behavior can no
longer proceed.
In addition, this approach conforms to what is likely widespread practice
among judges. If the Gupta, Madoff, and Stanford cases are any indicator,
judges are already engaged in neutralization inquiries. Such inquiries also
have the benefit of not sacrificing the positives of increased individualized
sentencing, especially considering how little we actually know about
neutralizations. If it is true that not all neutralizations are uniformly “bad,”
it may be that the overall goals of sentencing are best furthered by judges
considering and crediting benign neutralizations, even at the risk of
marginally enabling some white collar crime. Allowing, and even
encouraging, neutralization inquiries lets judges practice individualized
sentencing, yet still publically reject “toxic” neutralizations. This balanced
and flexible approach stays true to the normative underpinnings of Pepper
and § 3553(a), while providing courts with an opportunity to disrupt the
mechanisms that make at least some white collar crime possible.
Regardless of where the line is drawn between encouraging some
neutralizations and discouraging others, judicial inquiry into the
neutralizations defendants employ must be transparent. Sentencing
transparency was one of the twin goals of the Sentencing Reform Act, and
it is no less important today.301 As evidenced by the Gupta, Madoff, and
Stanford cases, some courts’ sentencing determinations are being
influenced by offender neutralizations. But precisely what inquiries are
being made, under what circumstances, and to which defendants is unclear.
Nor is it clear how much judges truly understand about the role of
neutralizations in the etiology of white collar crime. In order for judges to
make effective sentencing inquiries and properly credit or reject defendants’
neutralizations, judges must be better educated as to the causes of white
collar crime. At the same time, in order for sentencing policymakers to
evaluate the effectiveness of these inquiries and how they affect federal
sentencing as a whole, judges must memorialize their sentencing
determinations, including their search for the why of white collar crime.
301. See U.S. SENTENCING COMM’N, supra note 208, at 3–4; see also STITH & CABRANES,
supra note 208, at 38–77.
[Vol. 82
“When you ask people why they commit crime, they make sounds. I call
them verbalizations. These are data. You study them.” 302 That is how
Donald Cressey, the pioneering white collar criminologist, described his
research into what would become known as offender neutralizations, the
psychological mechanisms white collar defendants employ to free
themselves from social norms and engage in criminal behavior. Cressey
spent his career searching for the why of white collar crime, trying to
understand what caused “good people” to commit terrible breaches of trust.
As the cases of Rajat Gupta, Peter Madoff, and Allen Stanford
demonstrate, judges are also engaging in this inquiry, and it is having an
impact at sentencing. This Article set out to explore this previously
unexamined aspect of white collar sentencing, primarily through the
criminological theory of neutralizations, which is particularly compelling in
describing the etiology of white collar crime. The sentencings of Gupta,
Madoff, and Stanford highlight how defendants may rationalize their
conduct through eight different neutralization techniques specific to white
collar offenders, and how judges credit some of those neutralizations as
sentencing mitigators while rejecting others. Although judicial inquiry into
offender neutralizations raises legitimate concerns, on the whole
neutralization inquiries appear beneficial.
When undertaken in a
transparent manner by judges educated about the role of neutralizations in
white collar cases, these inquiries can increase individualized sentencing
and even potentially disrupt the mechanisms that cause some white collar
crimes. Therefore, they should become a larger part of the white collar
sentencing discussion.
302. Maruna & Copes, supra note 11, at 222 (quoting Interview with Edwin M. Lemert,
Professor Emeritus, Univ. of Cal., Davis (Mar. 16, 1979), in CRIMINOLOGY IN THE MAKING:
AN ORAL HISTORY 118, 139 (John H. Laub ed., 1983)).

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