The Washington PostDemocracy Dies in Darkness

Why might Trump have wanted Judge Cannon for his Mar-a-Lago challenge?

A page from the order granting a request by former president Donald Trump's legal team to appoint a special master to review documents seized by the FBI during a search of his Mar-a-Lago estate. (Jon Elswick/AP)

A guiding idea of the U.S. legal system is that justice is blind. That Americans can and should have confidence that judges will reach decisions based on facts and colored as little as possible by their own political inclinations. When criticism of a decision is accompanied by a mention of the president that appointed the judge, there’s often scolding that follows: the implicit suggestion that politics played a role is an erosion in confidence in the system.

Then we have the case of U.S. District Judge Aileen M. Cannon.

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On Monday, Cannon ruled in favor of a “special master” to review material seized from former president Donald Trump’s Mar-a-Lago resort last month. Cannon had telegraphed her intent to do so a week prior, even before the Justice Department had offered its argument against doing so.

A special master — often a former judge — is often appointed by a court to review material to which investigators shouldn’t have access, such as material privileged under attorney-client confidentiality. Cannon’s order, though, included various unusual stipulations, such as preventing the Justice Department from including seized material in its investigation until the special master’s review was concluded. She also tasked the special master with evaluating Trump’s claims of executive privilege, though of course the Justice Department is part of the executive branch.

When legal experts weren’t baffled by Cannon’s stipulations, they were often critical. For Trump, though, the decision was a sweeping victory, introducing a robust roadblock between the government investigation into his behavior and the evidence it collected in the search of his Florida event venue.

As you might have gathered, Cannon is a Trump appointee. She was one of four nominees made by Trump on May 21, 2020, as Trump was highlighting the number of conservative judges he had seen confirmed to federal courts. (Republicans, he tweeted two weeks earlier, “should LOVE our 280 new Judges,” which is an overestimate of the actual number.) Of the four, Cannon was the only one evaluated as “qualified” by the American Bar Association; the other three were evaluated as “well qualified.”

But she was young — she’s in her early 40s — and therefore could serve on the bench for a long time.

“As of this point,” the legal blog the Vetting Room wrote at the time, “the Trump Administration has made an art form of finding attorneys who barely squeeze in under the twelve year practice requirement that the American Bar Association seeks for judges.”

The blog figured that Cannon would nonetheless be confirmed, as she was — nine days after Trump lost his reelection bid. A number of Democrats joined the majority, though most of the party’s senators opposed her.

Among those supporting her confirmation was Sen. Dianne Feinstein (D-Calif.). In written questions, Feinstein had challenged Cannon on her membership in the conservative Federalist Society, an organization that Trump at one point said would be the primary source of recommendations for his Supreme Court nominations. Asked by Feinstein how the Federalist Society planned to “reorder priorities within the legal system,” as its website had argued, Cannon (understandably) indicated she wasn’t familiar with the statement.

All of this is (and has been) grist for skepticism about her decision Monday. But perhaps the best signifier that Trump might find her to be sympathetic is how eagerly his attorneys may have sought her out.

In a thorough review of Cannon’s background, the Daily Beast’s Jose Pagliery notes that Trump’s failed, baseless effort to sue Hillary Clinton for the Russia investigation this year was filed with the apparent hope that Cannon would assess the case.

Pagliery wrote that “when his attorneys formally filed the paperwork, they selected a tiny courthouse in the sprawling federal court district’s furthest northeast corner — a satellite location that’s 70 miles from Mar-a-Lago. They ignored the West Palm Beach federal courthouse that’s a 12-minute drive away.”

The former being Cannon’s courtroom.

The judge who actually got that case, however, was appointed by President Bill Clinton, and he commented on the ploy after Trump’s attorneys tried to argue that he was biased: “when Plaintiff is a litigant before a judge that he himself appointed, he does not tend to advance these same sorts of bias concerns.”

It’s certainly not uncommon for attorneys to seek out favorable judges or venues. But that these cases involved a president’s team evaluating judges that the president himself had appointed? That is. So why might Trump’s team have thought that Cannon would view his case so favorably? There are multiple other judges in the same district whom Trump had nominated, after all. How should we view this?

The pattern, in other words, went like this: Trump, working with then-Senate Majority Leader Mitch McConnell (R-Ky.), pushed hard to fill vacancies on the bench (often ones held open by McConnell). He campaigned on filling those seats with ideological allies and often offered up nominees who checked two boxes: young and conservative. Then, out of office and finding himself in need of a judge’s favorable opinion, he sought out Cannon in particular. On Monday, that paid off — leaving legal observers perplexed (or worse).

Again, the system depends on Americans having confidence in the impartiality of the judiciary, just as it depends on our having confidence in the objectivity of institutions like federal law enforcement. Trump’s worked hard to undercut that confidence (in both cases). But even those who are now Trump supporters have grown increasingly skeptical of institutions such as the Supreme Court — particularly in the wake of the court’s clear shift to the right.

We’re asked to rest easy that Cannon’s decision is uncoupled from her path to the bench, to be confident that her opinion was based on the evidence at hand (despite her indicating before that evidence was available that she was likely to end up where she did). If you’re inclined to think she might have been unusually sympathetic to the former president, though, you do appear to have some company: Trump’s own attorneys.