Raymond Dearie's appointment as special master to review records the FBI seized from Mar-a-Lago was a positive development for former President Trump, whose lawyers recommended him. But their call for the low-profile New York judge was befuddling given Dearie has no apparent connection or loyalty to Trump.

Driving the news: Two sources with direct knowledge of the closely held deliberations now tell Axios what Trump's legal team was thinking:

• Lawyers and advisers to the former president believe Dearie's role on the secretive court that approved controversial warrants used to surveil former Trump campaign aide Carter Page in 2016 and 2017 made Dearie a deep skeptic of the FBI.
• The two sources were granted anonymity because they were describing sensitive discussions within the Trump team.

Details: Dearie's seven years on the Foreign Intelligence Surveillance Court, including during the Page case, is a matter of public record and has been reported. But it has not been previously reported that this experience drove the Trump team's thinking in requesting him.

• Dearie could not be reached for comment. He has not made any public comments — that Axios is aware of — to suggest that the Trump team's thinking is more than a hope or a theory. And, he will be reviewing the documents themselves for privilege, not reviewing representations about the documents by the FBI.
• A representative for the United States District Court for the Eastern District of New York — the court on which Dearie has served since 1986 — did not respond to questions about whether Trump team's understanding of Dearie's view of the FBI matches his actual view.
• Taylor Budowich, a spokesperson for Trump, did not respond to a request for comment.

Why it matters: As special master, Dearie will vet more than 11,000 documents seized from Mar-a-Lago for both attorney-client privilege and executive privilege to determine if any material was improperly swept up in the search.

• His appointment could, at a minimum, delay the Justice Department's investigation into the former president. The department has argued that such a delay could harm U.S. national security because of the sensitive nature of the highly classified documents Trump improperly kept at Mar-a-Lago.

Flashback: The Justice Department's investigation into Russian election interference in the 2016 presidential election and connections to the Trump campaign involved a flawed process.

• Dearie, 78, served for seven years on the FISC. He was one of the judges who signed off on FISA warrants to surveil Page.
• Two of the four approved warrants were later declared invalid after a DOJ Inspector General report found a series of misstatements and omissions in the FBI's applications to get the warrants.
• A former FBI lawyer, Kevin Clinesmith, pleaded guilty in 2020 to altering an email submitted as part of the surveillance application — a felony charge.

The FISA process typically is not adversarial in real time because people who do not know they are under surveillance cannot push back against FBI claims in court.

• Judges historically have appeared to give the FBI significant deference in these cases. But the Page saga showed how that trust could be misplaced.
• Trump's lawyers are betting that has made Dearie more skeptical of the FBI than an average judge — in a way that endures beyond the Page case.

Between the lines: Trump has a history of demanding loyalists in key roles, which made his team's suggestion of Dearie as special master a puzzle to many legal observers.

• Dearie, whom former President Reagan appointed to the federal bench in 1986, is widely respected in the legal community and has a reputation as an "exemplary jurist" and a straight-shooter.
• Since the announcement, Dearie has even received praise from Trump enemies. Andrew Weissmann, a former lead prosecutor in the Russia investigation who appeared before Dearie early in his career, told the New York Times that Dearie was "a fair-minded, smart judge who has a ton of common sense..."
• Dearie's bipartisan high esteem worked to Trump's benefit. U.S. District Court Judge Aileen Cannon, a Trump appointee in the Southern District of Florida, did not face pressure to reject Dearie as she would have with a recommendation of someone seen as a Trump loyalist.
• Dearie was not on the Justice Department's list of recommended special masters, but the DOJ accepted the recommendation from Trump's team due to his "previous federal judicial experience and engagement in relevant areas of law."

Since 2011, Dearie has been on "senior active" status, meaning he has a reduced caseload but continues to preside over cases, as his court calendar suggests.

• Two days after Trump made his request for a special master, Dearie told Law.com he would move to inactive status.
• Two weeks later, Trump's lawyers submitted Dearie's name to DOJ as one of two recommendations for the role. It is not clear whether or how those developments are connected.

What's next: Cannon said Dearie will need to complete his review of materials by Nov. 30 — a timeline closer to the Trump team's suggestion than to DOJ's proposed deadline of Oct. 17.

• The Nov. 30 deadline could shift subject to Dearie's own proposals. Cannon also asked Dearie to submit interim reports and recommendations on documents before his entire review is complete.
• In granting the request for special master, Cannon also temporarily barred law enforcement agencies from accessing the material for their investigation of Trump's handling of the documents until the special master review is complete.
• After Cannon rejected DOJ's request to allow investigators to continue reviewing classified documents, the DOJ asked the U.S. Court of Appeals for the 11th Circuit to issue a partial stay of Cannon's order.