Debevoise, DOJ Sentencing Reform Clash Could Hit Supreme Court

Welcome back to the Big Law Business column. I’m Roy Strom, and today we look at how a Debevoise & Plimpton pro bono project might end up before the Supreme Court. Sign up to receive this column in your Inbox on Thursday mornings.

John Gleeson has fought to scrub away what he calls the injustice of “stacked” mandatory prison sentences in the eight years since he left the federal bench. The Debevoise & Plimpton partner’s work could soon face its toughest test: a face-off with the Justice Department at the US Supreme Court.

Gleeson, an ex-prosecutor, spent two decades as a federal district judge in Brooklyn before joining Debevoise in 2016. He’s the driving force behind “The Holloway Project,” a massive pro bono program focused on criminal justice reform.

The project typically represents middle-aged Black men convicted of robberies or other crimes using a firearm. They were sentenced under a since-repealed mandatory minimum provision that stacked consecutive decades-long terms on top of one another. Debevoise’s goal is to reduce the sentences for clients they believe have been rehabilitated after decades in prison.

The project is named for Francois Holloway, who Gleeson himself sentenced to 57 years behind bars in a robbery case. Holloway’s prison term was reduced in 2014 after Gleeson made a personal appeal to Loretta Lynch, then the top federal prosecutor for the Eastern District of New York.

A growing team of Debevoise lawyers have successfully represented 55 people to date, getting their prison sentences reduced by 2,230 years combined, according to the firm.

The project is now facing legal jeopardy. The DOJ is challenging Sentencing Commission guidelines that became effective in November, which Debevoise and others have used to obtain reduced sentences in some cases.

“It’s going to rocket its way to the Supreme Court,” Gleeson said in an interview.

Not an Innocence Project

This is no innocence project.

Debevoise’s clients have been convicted of crimes involving firearms. The project’s goal is not to overturn those convictions, but to reduce punishments that the lawyers call overly harsh and the Sentencing Commission has repeatedly said were applied disproportionately to Black defendants.

The punishments were the product of a federal law that allowed prosecutors to seek mandatory, consecutive minimum terms of up to 25 years for multiple firearms offenses. This “stacking” could apply to multiple charges brought in the same case—meaning defendants could serve life sentences for their first criminal case.

That’s what happened in Holloway’s case, though the mandatory terms were slightly lower when he went to trial in 1995. After being found guilty of three armed carjackings, he was sentenced to 57 years in prison. Only about 12 years were for the carjackings. The remaining 45 years were a result of the “stacked” sentences.

Criminal defendants could avoid the stacked charges by pleading guilty. Co-defendants in prosecutions against the project’s clients often spent 10 years or less in prison. Holloway passed up a nine-year sentence offered in a plea deal.

The First Step Act put an end to such harsh sentencing in 2018. The bipartisan criminal justice reform law slashed minimum sentences by as much as 40 years in many cases.

The law did not make those changes retroactive, but Gleeson and his team seized upon it anyway. They focused on a provision that expanded judges’ ability to reduce sentences for “extraordinary and compelling” reasons.

Gleeson’s team and others convinced some courts that one such reason was the vast discrepancy between the sentences their clients received under the former guidelines compared to the sentences they would receive today.

Other courts shot down the argument, calling it an effort to end-run Congress’ decision to not make that provision of the law retroactive. With federal appellate courts split on the issue, Debevoise asked the Supreme Court to take it up in 2021.

The Justice Department argued it was premature to take up the cases, noting the law directed the Sentencing Commission to define these “extraordinary and compelling” reasons, and it had not yet done so. The Supreme Court did not hear the case.

It’s likely not the last time the Supreme Court will be asked to weigh in, thanks to new developments.

New Guidelines

The Sentencing Commission guidelines went on the books in November, and they essentially dovetail the Debevoise arguments.

The guidelines allow criminal defendants who have served at least 10 years in prison to seek sentence reductions based on changes to laws that occurred after the sentencing. A court can reduce a sentence in this situation if it finds a gross disparity between the original punishment and that likely imposed under the new law.

Gleeson is a member of the commission and was involved in developing the guidelines.

The problem is that the Justice Department has a different point of view. The agency continues to fight efforts to reduce sentences in several cases, arguing that the commission exceeded its authority by effectively making the excessive sentence reduction portion of the law retroactive.

“What [DOJ] said very early on is that their nationwide litigation position was that they are objecting to this provision as an overstep from the Sentencing Commission,” said Erica Zunkel, who teaches at the University of Chicago and has collaborated with Debevoise lawyers. “The DOJ is more or less rolling out the same legal arguments in every case that raises this issue across the country.”

That marks a turnabout for the agency, which had previously urged the Supreme Court to wait until the Sentencing Commission made the rules Congress required.

The DOJ has “contradicted itself” by now arguing that the commission doesn’t have the power to answer those questions, according to US District Judge Timothy Batten.

“How can the Commission have the authority to address the question but exceed that authority by addressing the question?” Batten wrote in a case last month. “This argument lacks merit.”

Batten agreed to reduce the defendants’ sentence over prosecutors’ objections.

The issue is currently before district judges and some appeals courts in various cases. Gleeson and others expect it will ultimately reach the Supreme Court.

“I would not be surprised if the Supreme Court did take it up,” said Elizabeth Blackwood, who has represented Debevoise co-defendants in her role as counsel and director for the First Step Act Resource Center at the National Association of Criminal Defense Lawyers.

It is a fight that Gleeson won’t be able to lead. He’s recused himself from arguments involving the commission’s new guidelines, citing his role as a member of the commission.

Gleeson won’t get a full reprieve. He has his own commercial practice.

And the Holloway project is in capable hands, with Debevoise partner David O’Neil poised to lead appeals efforts. Before joining Debevoise in 2015, O’Neil ran the Justice Department’s criminal division.

Worth Your Time

On Quinn Emanuel: Last week, we wrote about Quinn Emanuel’s judgment preservation insurance policy. This week, we found out we were right: The firm insured about 90% of the $185 million award.

On Kirkland & Ellis: Jamie Sprayregen, the Kirkland partner who founded its preeminent restructuring practice in 1990, is leaving the law firm after 30 years to join financial advisory firm Hilco Global.

On The Big Four: KPMG sees an opportunity to grow its legal business by outspending major law firms on artificial intelligence tools, with the the Big Four consultancy planning to invest “tens of millions of dollars” to help corporate legal departments streamline operations, including implementing generative AI.

That’s it for this week! Thanks for reading and please send me your thoughts, critiques, and tips.