The New York mob boss John J. Gotti rose in court one day in 1991 as he was nearing trial and jabbed his finger at the baby-faced Brooklyn prosecutor handling his case.
Dismissing his opponent — a young government lawyer named John Gleeson — as “Little Lord Fauntleroy,” Mr. Gotti claimed that Mr. Gleeson was in over his head. “He can’t handle a good fight,” Mr. Gotti snarled, “and he can’t win a fair trial.”
Within eight months, Mr. Gotti had lost the trial, and Mr. Gleeson, then 38, rode the victory into a long career as a prosecutor, judge and private lawyer.
That career took an unexpected turn this week when Mr. Gleeson, now 66, was called back into government service to take part in a case that could easily prove as bruising as his brush with the famous don.
On Wednesday, the federal judge overseeing the case of President Trump’s former national security adviser Michael T. Flynn appointed Mr. Gleeson to oppose the Justice Department’s plan to drop the charge. The position, as a kind of legal adviser to the judge, Emmet G. Sullivan, was both unusual and slightly ill-defined, and was certain to thrust Mr. Gleeson into an open confrontation with Mr. Trump and his army of supporters.
Mr. Gleeson was well positioned to handle the job, a half-dozen of his colleagues said in interviews.
“If Judge Sullivan was looking for a straight arrow, he got one,” said Judge Raymond J. Dearie, who hired Mr. Gleeson as a prosecutor in the early 1980s and later served with him on the Brooklyn federal bench. “John is an extremely talented lawyer who calls them as he sees them.”
Mr. Flynn pleaded guilty twice to lying to investigators as part of a larger inquiry into Russia’s interference in the 2016 presidential election. But he later sought to fight those charges, asking Judge Sullivan to allow him to withdraw his guilty plea.
The Justice Department stepped into the fray last week and abruptly moved to drop the case after a long campaign by Mr. Trump and his supporters. The reversal prompted accusations that Attorney General William P. Barr had undermined the rule of law and further politicized the department.
While many of the details of Mr. Gleeson’s post remain unclear, Judge Sullivan has tapped him to represent the viewpoint of the original prosecutors who believed that Mr. Flynn had committed a crime.
At this point, both the government and defense agree that the charge against Mr. Flynn should be dismissed. Judge Sullivan has asked Mr. Gleeson to be something like a shadow prosecution, marshaling arguments — discarded by Mr. Barr — as to why the charge should remain. Judge Sullivan has also asked Mr. Gleeson to determine whether Mr. Flynn should face an additional charge of perjury.
Raised in Westchester County by an Irish immigrant family, Mr. Gleeson worked as a caddy at a local golf course before attending Georgetown University. As he prepared himself for a law career, he made his living painting houses.
He joined the U.S. attorney’s office in Brooklyn in 1985 and was quickly assigned to the case of Mr. Gotti, the era’s most renowned and ruthless gangster. Mr. Gleeson was a junior member of the prosecution team in 1986 when Mr. Gotti was tried for the first time. He was acquitted the following year.
After a second acquittal in a state case, Mr. Gleeson oversaw a third trial of Mr. Gotti and in 1992 he prevailed, largely by winning the cooperation of Mr. Gotti’s right-hand man, the assassin Salvatore Gravano.
“There was a feeling among our generation of prosecutors that John was a rock star,” said Gordon Mehler, who worked with Mr. Gleeson at the time. “He was super smart, but also incredibly hardworking. And he could take a punch.”
As a prosecutor, Mr. Gleeson had a reputation for being aggressive — perhaps, some said, overly so — and for taking a humorless, even cold, approach to lawyering. With his tight-lipped manner and wire-rimmed glasses, he was known around the office by a goody-two-shoes nickname: Clark Kent.
As a judge, however, his vision of the criminal justice system, and his sense of empathy, seemed to broaden.
“He began to see many of the inequities that people face — especially the poor and minorities,” Mr. Mehler said. “He became more liberal on criminal matters and a kind of champion for the down and out.”
Mr. Gleeson was an early advocate of federal sentencing overhauls and was a driving force behind bringing special drug courts to Brooklyn, working with an agency known as Pretrial Services to start a program that allowed drug-addicted defendants to avoid prison time by achieving sobriety. In more than two decades as a judge, he regularly visited prisons to ask inmates about the experience of being in custody.
In the financial sphere, Mr. Gleeson oversaw the government’s decision to defer the prosecution of the banking giant HSBC, which was accused of an array of money-laundering violations. While critics attacked the deal, which allowed HSBC to avoid criminal charges, as a slap on the wrist, Mr. Gleeson monitored it regularly to ensure the bank’s compliance, warning prosecutors that such agreements were still subject to judicial oversight.
When Mr. Gleeson left the bench in 2016 and went into private practice, he continued his work on sentencing changes in between more white-collar cases. In the past few years, he has helped free inmates whose prison terms were found to be egregious.
He may have caught Judge Sullivan’s eye this week when he co-wrote an opinion article for The Washington Post, noting that the judge could reject the Justice Department’s motion to dismiss the charges against Mr. Flynn if he wanted. The headline said it all: “The Flynn Case Isn’t Over Until the Judge Says It’s Over.”
According to Kelly T. Currie, the former acting U.S. attorney in Brooklyn, Mr. Gleeson’s experience as a prosecutor, a defense lawyer and a federal judge made him well suited to help Judge Sullivan sort through the case.
“He’s meticulous and listens carefully to all the arguments before reaching a decision,” Mr. Currie said. “He’s somebody who takes the law very seriously.”
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