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How Debevoise Scrubbed 1,000 Years From ‘Unjust’ Prison Terms

March 10, 2022, 10:55 AM

Welcome back to the Big Law Business column on the changing legal marketplace written by me, Roy Strom. Today, we look at how a former federal judge at Debevoise built a project to undo “stacked” sentences. Sign up to receive this column in your inbox on Thursday mornings.

One case stuck with John Gleeson more than just about any other during his 20-plus years as a federal judge. In 1996, his second year on the bench, Gleeson was forced to sentence a defendant to a 57-year prison term—after the man passed up the government’s 11-year plea deal offer.

In an extraordinary move, Gleeson convinced U.S. Attorney General Loretta Lynch to allow for the defendant, Francois Holloway, to be released in 2014. Holloway served nearly 20 years for a series of armed car-jackings that cost his co-defendants no more than six years behind bars, all because he wanted to go to trial.

Gleeson has since left the bench and is now a partner at Debevoise & Plimpton in New York. He’s using new tools to build on his earlier work undoing mandatory criminal sentences he calls “unjust” and “completely indefensible.”

“They’re ridiculously long,” Gleeson said of so-called “stacked sentences.” “And they are not imposed because the prosecutors made some determination that these were defendants especially in need of incapacitation.”

Gleeson and a team of more than 100 associates at Debevoise have so far helped 34 prisoners reduce the type of “stacked” sentence Holloway received, which are harsh, mandatory sentences initially meant to punish repeat firearm offenders. Critics say eventually became a blunt-force tool against first-time offenders who passed up guilty pleas.

The pro bono effort has shaved off more than 1,100 years in prison time so far, Gleeson said. He expects a 35th prisoner will receive a sentence reduction this week in Utah.

Gleeson’s “Holloway Project” no longer relies on the limited mercy of federal prosecutors. It’s been aided by a 2018 law, the First Step Act, allowing his team to successfully litigate requests for compassionate releases. The law firm has spent more than 15,000 hours of lawyer-time on the project, according to Gleeson.

The project began after Philando Castile, a 32-year-old Black man, was shot and killed by a Minnesota police officer, sparking nationwide protests over the use of force by police. Debevoise held an all-employee meeting where Black employees spoke about the impact of racism in their lives, Gleeson recalled.

Gleeson spoke, too, and the firm asked him what it could do to make an impact. He’d received hundreds of letters from inmates serving mandatory stacked sentences, hoping he could help them the way he did Holloway.

The sentences, which prosecutors have discretion to deploy, had a history of racial bias, detailed in three separate U.S. Sentencing Commission reports beginning in 2004. Black offenders accounted for nearly 53% of mandatory minimum sentences resulting from firearms offenses—far more than any other racial group, a 2018 Sentencing Commission report found.

“I thought here is the one discrete racial inequity that, in my mind, is kind of hair-raising,” Gleeson said. “These guys are going to die in prison.”

The statute creating “stacked” sentences—known as a Section 924(c) charge—was initially intended to punish repeat offenders. It required mandatory, successive 20-year sentences for a “second or successive” firearm-related conviction. The sentences were upped to 25 years each in 1998.

But the U.S. Supreme Court ruled in 1993 that the charge could apply to crimes that occurred simultaneously, rather than after an initial conviction. Threatening a minimum of 45 years in prison for a defendant’s first conviction became leverage for prosecutors to obtain guilty pleas.

In Holloway’s case, all three of his armed carjackings occurred in a 24-hour period. He got 12 years for the carjackings, plus 45 years for the stacked charges. The gun was never fired during the carjackings.

When Gleeson’s project started in 2016, he had no legal remedy to offer clients. He was asking U.S. Attorneys across the country to do what Loretta Lynch had done—review the cases and offer mercy.

He got nowhere.

“To a person, they said no,” Gleeson said.

The big break came in 2018 when President Donald Trump signed into law the First Step Act, a bipartisan bill that did two crucial things. First, it abolished the practice of stacking multiple 924(c) charges in a defendant’s first case—though that change was not retroactive. Second, it allowed defendants to petition for compassionate releases, which could previously only be brought by the Bureau of Prisons.

The compassionate release statute gives judges discretion to reduce sentences if they agree there are “extraordinary and compelling” reasons to do so.

Now, Gleeson’s in the position of litigating against some of the same prosecutors he’d previously asked for mercy. Some still fight him “tooth and nail,” he said.

“One intractable part of our system is the tenacity bordering on ferocity with which prosecutors just cling to the results in old cases,” he said. “It is unbelievably frustrating.”

Gleeson uses a handful of arguments to convince judges.

Congress doesn’t even allow these types of sentences anymore, he tells them. He says he points out all his clients have a track record of good behavior and rehabilitation in prison. He also shows that many of their co-defendants, like Holloway’s, received significantly shorter prison sentences from guilty pleas.

One argument that Gleeson no long makes: that stacked sentences were disproportionately employed against Black defendants.

He’s found prosecutors object to the idea—Gleeson says he was told by one prosecutor he should be disciplined for insinuating he was personally racist. And no judge has cited the sentences’ racial bias in the 34 rulings siding with his clients, he said.

“Nobody ever disputed it. DOJ doesn’t dispute it at all,” he said. “It just immediately devolves into some personal issue.”

Gleeson’s work has a long way to go, considering more than 2,500 stacked sentences were handed out. His team continues to screen cases, file motions, and work with public defenders around the country to assist on their similar motions.

Gleeson has done all this while handling other matters at Debevoise, including being tapped by a federal judge to argue against the Justice Department’s decision to drop charges against Trump’s former national security adviser Michael Flynn. His 73-page brief argued the decision was a political favor and constituted “gross prosecutorial abuse.” The charges against Flynn were eventually dropped, however.

Gleeson said at least one other Big Law firm, Davis Polk & Wardwell, has started working on these cases after a training session with the Debevoise team. A Davis Polk spokeswoman confirmed the firm was working on two cases.

Academics have also paid attention to the project. Ever since federal parole was eliminated in the late 1980s, there’s been an interest in developing a “second look” at some convictions and sentences.

“People change over 20 years,” Gleeson told me. “And what our project has proven is that now there is a way for even people who committed violent crimes with firearms to get a second look.”

Worth Your Time

On Big Law and Russia: At least four more Big Law firms said they will close their Russia offices. They include Latham & Watkins, Squire Patton Boggs, Freshfields Bruckhaus Deringer and Morgan Lewis & Bockius, Meghan Tribe reports.

On Big Law Cash: Big Law’s pay war is exposing deep fault lines between the richest law firms and everyone else, Tribe reports. The costs of higher salaries are likely to weigh on firms with lower profits, especially if the economy takes a turn for the worse.

On Tesla’s Lawyers: Brian Baxter reports on the revolving door of top lawyers at Elon Musk’s Tesla. David Searle was name the third new legal chief in two years.

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

To contact the reporter on this story: Roy Strom in Chicago at

To contact the editors responsible for this story: Chris Opfer at; John Hughes at