NEW YORK — Raymond Dearie, a senior federal judge, has overseen an international corruption case involving the highest levels of professional soccer. He authorized a highly secretive warrant to surveil a former campaign aide to Donald Trump. And he’s spent years taking on mobsters in New York City.
But now, the 78-year-old Ronald Reagan appointee faces one of the thorniest legal tasks of his well-regarded career: sifting through files seized from Trump’s Mar-a-Lago estate.
A Florida-based federal judge on Thursday appointed Dearie to lead the “special master” review of those records amid a criminal investigation into the former president’s handling of documents marked classified.
U.S. District Judge Aileen Cannon’s decision came after Trump’s legal team and the Department of Justice both endorsed Dearie’s nomination — initially made by Trump — to parse the seized records for potentially privileged material.
Lawyers and litigants who have appeared before Dearie describe him as independent, thorough and even-handed jurist who is fit to wrangle the dueling sides. As much as any judge put in this difficult position, they say he’s up to the task.
“He’s one of the few judges who both sides want to appear in front of. He is held in the highest regard by attorneys. He’s someone who actually listens to the lawyers and considers what they have to say before he makes a decision,” said Lindsay Gerdes, a former Brooklyn federal prosecutor.
Sean Hecker, an attorney at Kaplan Hecker & Fink LLP who has had several cases before Dearie (including one pending) said much the same. “He’s independent-minded, extremely smart and wise. Hard to imagine a more qualified person for this challenging assignment.”
Dearie is a former U.S. Attorney for the Eastern District of New York, a job he held from 1982 to 1986. He was chief judge of the Eastern District from 2007 to 2011. He remains an active judge on senior status, meaning he has a reduced caseload.
He also served on the Foreign Intelligence Surveillance Court for seven years — where he was one of the judges who signed off warrants the FBI used to surveil 2016 Trump campaign aide Carter Page in an investigation into Russian election interference.
Federal investigators later determined an FBI lawyer altered an email used to support the surveillance application — something Trump has used to discredit the entire investigation — though a judge on the FBI attorney’s subsequent criminal case acknowledged the application might have been granted anyhow.
Some documents seized at Mar-a-Lago were marked “FISA,” indicating they relate to intelligence derived from foreign sources, according to an affidavit in the case.
“He works incredibly well with parties, but doesn’t tolerate nonsense,” said Richard Garbarini of Garbarini Fitzgerald P.C. “He will not allow parties, or attorneys, to play games, or play fast-and-loose with the rules.”
Though few, if any, cases will match the stakes and intrigue of the Mar-a-Lago investigation, Dearie does have some high-profile cases under his belt. Those include the corruption trials of several officials at FIFA, the global soccer governing body.
He also oversaw a court battle in the 2017 New York City mayoral race. Former New York City Councilmember Sal Albanese didn’t meet polling and fundraising thresholds to gain admittance into televised debates, and he sued the city’s Campaign Finance Board seeking an injunction so he could take the stage. But Dearie ruled the finance board’s criteria were not partisan, subjective or discriminatory.
Albanese did not prevail, but he came away with a positive impression of the judge.
“I think he’s a fair man, despite my losing that case. He’s obviously very knowledgeable,” he said in an interview. “His temperament was excellent, and he was thoughtful. He asked a lot of good questions. Very level-headed.”
Prosecutors and lawyers for Trump each presented Cannon with two options as candidates for the job: Dearie and Paul Huck Jr., a Florida attorney with significant ties to figures in Trump’s orbit.
The Justice Department proposed Barbara Jones — a former federal judge and Bill Clinton nominee who has filled the same special master role in three other sensitive investigations — and former federal appeals court judge Thomas Griffith.
Trump’s team objected to both of those picks while the DOJ indicated Huck was not acceptable because he had never served as a judge.
Alexander Coleman, an employment lawyer who has had several cases before Dearie — including a high-profile case where an NYPD cop alleged workplace retaliation after reporting colleagues who tried to blame him for another detective’s botched investigation — said he was impressed with the judge.
“He took a very difficult, thorny issue and he untangled it and reached the right result,” he said. “He’s very thoughtful and very contemplative.”
Dearie graduated from St. John’s University School of Law and has also worked as an attorney in private practice. He is originally from Rockville Center on Long Island.
The judge did not respond to a request for comment.