Former president Donald Trump speaks during the America First Policy Institute's America First Agenda Summit in Washington, D.C., on July 26, 2022.

Former president Donald Trump speaks during the America First Policy Institute's America First Agenda Summit in Washington, D.C., on July 26, 2022. (Al Drago/Bloomberg)

Donald Trump and the Justice Department don’t agree on much, but one thing they came to consensus on is a retiring federal judge in Brooklyn.

Raymond Dearie, who last month announced his intention to retire after more than 30 years as a judge, is the sole person among four candidates that both Trump and the Justice Department said they could support as a special master. If named by the Florida judge overseeing the case, Dearie would be tasked with reviewing thousands of documents seized from the former president’s Mar-a-Lago home to determine whether Trump’s privilege claims apply to any of them.

Dearie was nominated by President Ronald Reagan in February 1986 and has handled everything from organized crime to terrorism to corruption at FIFA, as well as national security cases while serving a rotation on the Foreign Intelligence Surveillance Court.

“Trump may think a Republican judge will help him, but it’s a big mistake to think that because Dearie is a Republican he’ll shade in favor of Trump in this case,” said Daniel R. Alonso, a former federal prosecutor in Brooklyn who served as chief of the office’s criminal division from 2002 to 2005. “Dearie is not a good pick for Trump here, because he doesn’t tolerate nonsense.”

Dearie is still an active judge, with senior status, on the Eastern District court, which includes three New York City counties as well as Long Island. A court official said he planned to take “inactive” status at the end of 2022. The Justice Department previously alerted U.S. District Judge Aileen Cannon in Florida that it would defer to Dearie and the court to hash out whether the special-master job would be considered “outside employment.” Federal judges face limits on taking other jobs and receiving compensation, but there are fewer restrictions for senior judges.

As a district judge, Dearie already has security clearance to view classified materials. The Florida judge has yet to rule on the Justice Department’s request to carve out from the special master’s review a key set of roughly 100 documents that the government says feature classified markings. Dearie didn’t respond to a request for comment for this report.

Andrew Weissmann, a former federal prosecutor in Brooklyn who was a senior member of special counsel Robert Mueller’s team, said Dearie is “basically the platonic ideal of a fair, wise jurist, and you will hear that from prosecutors and defense counsel alike.” He recalled that when he was a prosecutor, Dearie was once late for a court appearance and sent him and the defense lawyer personal handwritten notes apologizing.

Moe Fodeman, a former federal prosecutor in Brooklyn who’s now a partner at Wilson Sonsini Goodrich and Rosati in New York, recalled a sentencing hearing before Dearie that showed how seriously the judge took the issue.

“He literally stopped the sentencing, went back to chambers and thought about it,” Fodeman said. “It’s not uncommon for him to stop a proceeding to think about a thorny legal issue that presents itself rather than making a knee-jerk decision.”

Dearie was born in 1944 in Rockville Center in New York’s Nassau County on Long Island. He got his law degree from St. John’s University School of Law in 1969.

After law school, Dearie worked in private practice, then joined the government as an assistant U.S. attorney in the Eastern District of New York in 1971. He worked his way through the office ranks to become executive assistant U.S. attorney under U.S. Attorney Edward Korman.

When Korman left the office in 1982, Dearie stepped into the job. His tenure leading the office overlapped with Rudy Giuliani’s time as U.S. attorney in Manhattan. Giuliani, a Trump ally, declined an interview request through his lawyer Robert Costello. Costello wrote in a text that Giuliani had “nothing to do” with Trump’s process for choosing special-master candidates.

Dearie led the U.S. attorney’s office until 1986, when he was appointed to the district court. He handled cases ranging from al-Qaeda terrorists to white-collar criminals such as Jose Carlos Grubisich, the former Braskem chief executive whom Dearie sentenced to 20 months in prison for his role in a sweeping bribery plot tied to Brazil construction giant Odebrecht.

Dearie also served a seven-year rotation on the Foreign Intelligence Surveillance Court, an arm of the federal judiciary that mostly operates in secret because of the sensitive nature of the covert operations and national security interests at stake.

Dearie was one of several judges to sign off on a succession of warrants that the FBI sought to surveil Carter Page, an adviser to Trump’s 2016 campaign, as part of a broader investigation of Russian interference in the election. The Justice Department inspector general later concluded that federal investigators had made mistakes and omissions in its warrant applications to the court, fueling long-running criticism of the Russia probe by Trump and other Republicans.

Dearie told the New York Law Journal in August that he was moving to inactive status after 36 years on the bench. “I’m going to miss it,” he said.

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