(Photo by Win McNamee/Getty Images)

Yesterday wasn’t a great day in Trumpworld. I mean, it wasn’t the 200+ pages of hurt that Tish James unleashed today, but it was no bueno. After lucking into a young judge in Aileen Cannon willing to lose her legal credibility to bend to every whim of the Trump legal team — and do more than they even dared to ask for — you’d think the legal wrangling over the top secret documents seized for Mar-A-Lago were leaning Donald Trump’s way. (Well, at least until the 11th Circuit weighs in.) But it looks like asking for a special master to resolve the privilege issues may backfire spectacularly.

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As we all know, Judge Cannon acquiesced to Donald Trump’s demand for a special master in the case, and both sides in the dispute put up two names for consideration. The government just about tripped over themselves agreeing to one of the names Trump’s team offered, Eastern District of New York judge Raymond Dearie. And after the first hearing in the matter, putting Dearie on their list is hilariously being referred to as an own goal by Team Trump.

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Yes, Dearie was appointed to the federal bench by a Republican — Ronald Reagan to be specific. But his reputation for “integrity and objectivity” is beyond reproach, and his judicial outlook is described as “by the book.” From jump, this never seemed like the kind of jurist to sign off on some cockamamie theory Trump’s own lawyers have a hard time articulating in court.

So… why *was* he on the Trump list? According to reporting from Axios, internal Trump sources believed that one negative interaction, while he served on the on the Foreign Intelligence Surveillance Court, with the FBI — over the course of a 35 year judicial career — so permanently scarred Dearie that he’ll lean their way in this case.

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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.

In the Page case, Dearie signed off on a FISA warrant and it was later discovered the FBI lied on the warrant application:

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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.

But, so far, the past Page case doesn’t seem to be impacting Judge Dearie’s approach to the Mar-A-Lago case. Which is exactly what you’d expect from someone known — over a 35-year career on the bench  — for having integrity and objectivity.

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Kathryn Rubino is a Senior Editor at Above the Law, host of The Jabot podcast, and co-host of Thinking Like A Lawyer. AtL tipsters are the best, so please connect with her. Feel free to email her with any tips, questions, or comments and follow her on Twitter (@Kathryn1).

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Aileen Cannon, Courts, Donald Trump, Raymond Dearie