Bennett: The Art of Representing a Hall of Shame Offender at Sentencing

This blog post is based on a sentencing over which I presided on Tuesday, November 28, 2017. It was a “Welcome Back, Kotter” sentencing in the sense that I had already sentenced the African-American offender in 2000 to a 60-month mandatory minimum in a crack case. He did not do well on supervised release, violating less than 3 weeks after starting his term. The next year, I revoked his TSR and sent him back to prison for 24 months.

On November 28, 2017, he was before me on possession with intent to distribute methamphetamine. He had 24 criminal history points and 29 unscored convictions, including an assault on a police officer (in 1994) resulting in the officer being injured and unable to work for 8 months. The officer testified live at the sentencing.

The U.S. Attorney’s Office could have filed two § 851 enhancements—requiring a mandatory life sentence. They filed neither. The AUSA filed a powerful sentencing memorandum focusing on the offender’s terrible criminal history, failure to pay over $100,000 in back child support, history of noncompliance, and extraordinarily high risk of recidivism. The AUSA asked for both an upward departure and upward variance. The quantity of drugs was small, so the offender’s guideline range was only 130-162 months with a maximum of life.

After reading the prosecution’s brief, I thought it likely I would go up to at least 240 months —quite possibly much higher. I then read the AFPD’s sentencing memorandum on behalf of the offender. This AFPD appears before me on a regular basis and is an outstanding advocate. He conceded early in his brief that “Mr. *****’s sentencing presents a difficult balancing of aggravating factors (in particular, his criminal history) and mitigating factors (drug addiction, mental health issues, relatively low-level involvement in drug distribution….).” He then suggested I go up one level to a range of 140-175 months because of the offender’s criminal history. He argued each of the mitigating factors forcefully and suggested a sentence between 120-140 months.

I had many questions for both attorneys and the offender gave a very articulate, 27-minute long allocution without the usual script or even a note for guidance.

Six lessons learned from this sentencing:

1) Always concede the obvious. The offender’s criminal history was deeply troubling, and both defense counsel and the offender, during his allocution, recognized this. Defense counsel knew from prior experience I was going to go up because of the criminal history and he maintained his credibility by readily conceding that some upward variance or departure for under-representation of criminal history was warranted. The offender repeatedly stated that when he saw page after page of his criminal history in the PSR, he was deeply embarrassed, ashamed, and remorseful.

2) Don’t be an ostrich[1] – confront the most aggravating factors and do your best to minimize their effect on the sentencing judge. Both defense counsel and the offender explained how the death of several of the offender’s relatives, including his mother, triggered his addiction and addictive personality. They both commented that most of his prior convictions were misdemeanors—directly related to feeding his addiction. The offender’s sister and father wrote letters of support. Both were high achievers and extraordinarily successful in their professional and personal lives. I wondered how two siblings could have such different life paths. The offender, in his allocution, explained that his parents never married and lived worlds apart. His sister was raised by his father and he was raised by his mother, who was a drug addict in an extremely abusive relationship with his step-father.

3) Because the § 3553(a) factors involve weighing that which cannot be measured, don’t give up on the mitigating factors simply because the aggravating factors are so powerful. I did an upward departure/variance for under-representation of criminal history, but did not go nearly as high as I intended, because the arguments and allocution persuaded me that I was placing too much emphasis on the criminal history and not enough on the mitigating factors in the balancing process.

4) Remember the power of the cognitive anchoring bias. This cognitive heuristic should be studied and mastered by every lawyer—even transactional lawyers. In the criminal context, I recommend a prior article of mine: Confronting Cognitive “Anchoring Effect” and “Blind Spot” Biases in Federal Sentencing: A Modest Solution for Reforming a Fundamental Flaw, 104 J. Crim. L. & Criminology 101 (2014). By giving a range of 120-140 months, defense counsel, whom I greatly respect, knowingly or not, gave me a low-end anchor. It’s hard to resist some effect of anchoring, even when you realize it is happening. It’s such a powerful heuristic. The AUSA, who I equally respect, suggested that anything approaching 240 months was too high, even though the offender was eligible for a life sentence. Thus, knowingly or not, giving me a high-end anchor.

5) Do not underestimate the effect of a sincere apology. An astonishing thing happened in the offender’s no-note-or-script allocution. He told me that he never knew that the officer assaulted in his 1994 conviction, where he was sentenced to 180 days in jail, had been so severely injured that it took him 8 months of rehabilitation and speech therapy before he could return to work. He learned that for the first time when he heard the officer’s testimony that day in court. He then, without any prompting from defense counsel, asked for permission to address the officer in the back of the courtroom to apologize. Permission was granted and was followed by a very heartfelt apology. It was a deeply moving courtroom moment. See, Jeffrey J. Rachlinski, Chris Guthrie, and Andrew J. Wistrich. “Contrition in the Courtroom: Do Apologies Affect Adjudication?” 98 Cornell L. Rev. 1189 (2013).

6) Be prepared to carefully and diplomatically argue racial bias in sentencing. Earlier last month, the United State Sentencing Commission published a comprehensive report, using sophisticated multivariate regression analysis, to establish that similarly situated “Black male offenders received sentences on average 19.1% longer than similarly situated White male offenders” during the period of 2012-2016. Unfortunately, I was the only one in the courtroom who had read the report. When I asked counsel if they had read it, both candidly said “no.” If used carefully, this is a potent weapon for defense lawyers in representing Black offenders.

[1] Actually, ostriches get a bad rap. They do not bury their heads in the sand. Google “Do ostriches really bury their head in the sand?”

13 thoughts on “Bennett: The Art of Representing a Hall of Shame Offender at Sentencing

  1. shg

    I have to echo GPG’s comment, which raises the one factor we can’t control, the luck of the wheel. There are some judges who will listen to argument. And then there are some stone cold killers on the bench.

  2. CLS


    Thank you for your continued “The Art Of” posts.

    I have recommended them to my CDL colleagues as “Can’t Miss”

    This is a golden post.

    And your recent paper was illuminating too.


      1. Richard Kopf


        How about “stone cold” realism? By the way, you do have a way with words.

        All the best.


  3. Jake


    Thanks for sharing your experiences on the bench. Even for a layperson, this was a fascinating piece of writing.



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