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During his long career, Judge Dearie has overseen prominent criminal cases such as the corruption trials of officials at FIFA, the agency that governs international soccer. He has also handled politically sensitive matters, among them a court battle over who was allowed to participate in televised debates during the 2017 New York City mayor’s race.

Having served on the Foreign Intelligence Surveillance Court from 2012 to 2017, Judge Dearie also has extensive experience with classified proceedings. That experience will likely prove crucial given that Judge Cannon has asked him to begin his review with about 100 highly classified documents seized from Mar-a-Lago.

While sitting on the intelligence surveillance court, Judge Dearie signed off on warrants that the F.B.I. used to surveil Carter Page, a former campaign aide to Mr. Trump, during the bureau’s investigation into Russian interference in the 2016 election. Investigators later discovered that a lawyer for the F.B.I. had altered an email that was used to support the application for the warrant, a development that Mr. Trump and his allies have often used to discredit the larger inquiry.

Many lawyers who know Judge Dearie were surprised last week when Mr. Trump’s legal team suggested him as a candidate for the special master post, wondering if the former president’s lawyers really knew who they were proposing.

“Dearie is a fair-minded, smart judge who has a ton of common sense and has been on the bench for a long time,” said Andrew Weissmann, a former lead prosecutor in the Russia investigation who got his start in the Brooklyn federal courts. “If that’s not what the Trump people wanted, that’s definitely what they got.”

Everything about the search of Mar-a-Lago has taken place in an atmosphere of partisan politics and extreme public scrutiny. As Mr. Trump and his allies have lashed out at the F.B.I. and the Justice Department, federal officials have often felt the need to be more transparent in court filings than usual, agreeing last month to release a redacted version of the affidavit that had been used to apply for the search warrant.