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Fifty Shades of Gray: Sentencing Trends in Major White-Collar Cases

54 Pages Posted: 19 Feb 2016  

Jillian Hewitt

Yale University - Law School

Date Written: February 17, 2016


Between 1987 and 2005, federal judges sentenced defendants pursuant to binding Sentencing Guidelines that severely curtailed their discretion. In United States v. Booker, the Supreme Court held the mandatory Guidelines sentencing scheme unconstitutional and rendered the Guidelines advisory. This Note offers a picture of white-collar sentencing in “shades of gray.” It conducts an empirical analysis of sentencing decisions after Booker to assess the consequences of the return to judicial discretion. In particular, the Note examines major white-collar cases in the Southern District of New York, where many such cases of national and international significance are prosecuted. The Guidelines instruct judges in white-collar cases to calculate the amount of economic loss attributable to the defendant and apply a sentencing enhancement — often a sizable one — on the basis of that loss. The findings reveal that a significant majority of defendants in these cases receive sentences of imprisonment shorter than those recommended by the Guidelines. Moreover, when judges impose sentences below the Guidelines range, the resulting sentences are often dramatically shorter than those produced under the Guidelines. Based on these findings, this Note argues that the U.S. Sentencing Commission should revise its approach to white-collar cases in three ways. The Commission should amend the Guidelines to reduce the severity of the economic loss table; calculate economic “loss” differently; and add additional, though less severe, enhancements to punish pecuniary gain and intended loss. Absent such changes, judges will — and should — continue imposing sentences far below the Guidelines range. These proposed changes better capture the seriousness of the offense and the culpability of the offender, even if they do not resolve the fundamental tension between individualized sentencing and the rigid quantification that characterizes the Guidelines system.

Keywords: federal sentencing guidelines, United States v. Booker, white collar sentencing, empirical study, white collar crime

Suggested Citation

Hewitt, Jillian, Fifty Shades of Gray: Sentencing Trends in Major White-Collar Cases (February 17, 2016). Yale Law Journal, Vol. 125, No. 4, 2016. Available at SSRN:

Jillian Hewitt (Contact Author)

Yale University - Law School ( email )

P.O. Box 208215
New Haven, CT 06520-8215
United States

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