Bloomberg Law
Sept. 21, 2022, 3:45 PM

Judge Aileen Cannon Channels Her Inner Kavanaugh

Vivia Chen
Vivia Chen

Remember when John Roberts rebuked then-President Donald Trump for calling a federal jurist an “Obama judge”? The chief justice famously declared, “We do not have Obama judges or Trump judges, Bush judges or Clinton judges.”

It was uncharacteristic of Roberts to be so outspoken, but the right thing to say at the time, back in 2018. His remarks now seem awfully quaint.

If there’s any doubt there are Trump judges and everybody else, Aileen Cannon should settle it.

Earlier this month, Judge Cannon, who was appointed by the former president to a federal district court seat in the Southern District of Florida, granted Trump’s request for a special master to review government records seized from his Mar-a-Lago estate.

Though that decision was roundly criticized, she has since doubled down, rejecting the Justice Department’s request to exempt 103 classified documents from the special master’s review in order to continue its criminal investigation.

There are many reasons to be alarmed by Cannon’s decision—extreme deference to Trump juxtaposed with a dismissive attitude toward government concerns about classified information—but what immediately popped out at me was its sheer clunkiness.

“Plaintiff has not had a meaningful ability to concretize his position with respect to the seized materials,” she wrote, in siding with Trump. An eighth-grade English teacher could have a field day with that sentence alone.

Overall, her decision was so badly argued, so inelegant in the extreme, that it bordered on gaudiness—as if Cannon wanted to show how far off the rails she can go.

“It’s hard to write clearly if the reasoning is muddled,” said George Washington University law professor Stephen Saltzburg, now serving as special master in cases involving Iraq and Iran. Cannon’s appointment of a special master is “either superfluous or meaningless,” he added.

“If I’m in a SCIF [sensitive compartmented information facility]—and I’ve been there many times—and I see a document that has classified markings, I have to assume it is classified.”

“The opinion is legally incoherent,” said Peter Shane, a scholar in residence at NYU Law School and the author of Democracy’s Chief Executive. “As someone who studies executive power, my view is that she’s either oblivious or uncaring about the legal framework surrounding executive privilege.”

‘Deeply Flawed’

Contrary to critics who suggest that she’s not up to the job of federal judge, I think Cannon knows exactly what she’s doing. The only question is whether her gamble will pay off.

Before Cannon went whole hog for Trump, did anyone even know who she was? Confirmed in November 2020 after Trump lost the election, she wasn’t a controversial nominee. Twelve Senate Democrats even voted for her.

She had the credentials that made her an acceptable, though hardly distinguished, choice for the federal bench.

A 2007 honors graduate of the University of Michigan Law School and member of the Federalist Society (naturally), she clerked for federal appeals court judge Steven Colloton, worked three years at Gibson, Dunn & Crutcher’s Washington office, then joined the US Attorney’s office in South Florida.

Though Cannon has the right notches on her belt, there’s no indication she was a star in any of those endeavors.

But the obscure Cannon is no more. Since issuing her decision, she’s been in the spotlight, facing a barrage of criticism from all sides.

On Fox News, former attorney general Bill Barr called the ruling “wrong” and “deeply flawed in a number of ways.” He also told The New York Times exactly what he thought of the appointment of a special master: “I think it’s a crock of shit.”

Even the ultra-conservative scholar John Yoo, author of the “torture memos” that justified harsh interrogation techniques during the George W. Bush presidency, seems puzzled by Cannon’s reasoning.

“It is not whether Trump violated the law. He did,” Yoo said in an interview at the National Conservatism Conference. “It’s not whether the government had legal grounds for the search warrant. It does. The question is really whether he could be charged.”

But the more Cannon is under attack for siding with the former president, the more her stock will rise with Trump—and that could be her plan.

Like Brett Kavanaugh who raged before the cameras during his Supreme Court confirmation hearings, when there was speculation that the former president might withdraw his nomination after the sexual assault charges made by Christine Blasey Ford, Cannon is strutting her stuff for her man Trump.

Familiar Playbook

By now, it’s a familiar playbook. If you want to soar in Trumpland, you have to play it to the hilt. What better way for an ambitious young judge, possibly with Supreme Court aspirations, to get ahead of the pack?

And whether or not Trump ever returns to power, the 41-year old Colombian-born jurist has carved out a role for herself as a Trumpian conservative.

For now, all eyes are on special master Raymond Dearie, a judge in the Eastern District of New York. “I think he will complete the job by the end of October,” Salzburg said. “It’s not his job to determine whether a document should be classified. I mean it when I say it should be a pretty easy job.”

Indeed, Dearie seems intent on moving quickly, and Trump’s lawyers are balking. Already, they are protesting Dearie’s proposal that both sides finish review of documents by Oct. 7.

“We respectfully suggest that all of the deadlines can be extended to allow for a more realistic and complete assessment of the areas of disagreement,” responded Trump’s lawyers to the special master.

They are also protesting Dearie’s request that they submit details about the declassification of records, arguing it will compromise their client’s defense.

At his first hearing on the matter Tuesday, Dearie expressed skepticism about some of the Trump team’s arguments.

So what happens if Dearie, who was proposed by team Trump, rejects the former president’s arguments? Rest assured, Cannon has thought of that. She wrote in her decision, “The Court reserves the right to remove the Special Master.”

What’s more, she’s not obligated to follow his decision. “She can disagree with the special master but I don’t think she will,” Salzburg said.

Shane added that it would be unseemly for Cannon to fire Dearie or disregard his decision, because “Dearie has more credibility—boatloads more—than she does.”

That’s placing a lot of hope that credibility still matters when it comes to impressing the king of Mar-a-Lago.

To contact the reporter on this story: Vivia Chen in New York at
Twitter: @viviachen
To contact the editor responsible for this story: Gregory Henderson at

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