In spring 2020, Aileen Mercedes Cannon was nominated by President Donald Trump to serve as a district judge in the Southern District of Florida. She was relatively young, not even 40, as well as somewhat inexperienced to serve as a trial-court judge, with only four jury trials under her belt.
But she was well-regarded in the South Florida legal community.
Her judicial career was off to a perfectly fine start. And her early law clerks had positive experiences.
And then, in August 2022, she was assigned Trump v. United States—the civil case that former president Donald Trump filed against the federal government, challenging the seizure of documents from his Mar-a-Lago estate and seeking the appointment of a special master to review them.
In September 2022, Judge Cannon largely ruled in Trump’s favor, ordering the appointment of a special master. Her ruling was widely criticized, and in December 2022, she was unceremoniously reversed by the Eleventh Circuit. The opinion was issued per curiam (“by the court” and therefore unsigned), but the panel consisted of Chief Judge William Pryor—a leading conservative jurist and Trump Supreme Court shortlister—and two Trump appointees, Judges Britt Grant and Andrew Brasher.
What went wrong? Based on her academic credentials and what I’ve heard about her from mutual friends, I disagree with criticisms of her as unintelligent; to the contrary, I believe she’s quite smart. But there’s a difference between intelligence and good judgment, and her ruling in Trump v. United States lacked the latter.
Many outsider observers dismiss Judge Cannon as a pro-Trump political hack. But sources of mine who know her personally push back on this, describing her as fair-minded and not particularly political.
So while she definitely leans too far in Trump’s direction, giving dubious arguments from his legal team more consideration than they deserve, I think it’s oversimplifying matters to dismiss all her rulings as purely the product of “MAGA judging.” Instead, I’d suggest that in her handling of Trump v. United States, Judge Cannon thought like a pointy-headed appellate judge, not a commonsensical trial judge.1 A seasoned trial judge would have seen Trump’s request for a special master and quickly ruled, “Hell to the N-O.” Judge Cannon—a former appellate attorney, with limited trial experience—received Trump’s unorthodox request, identified novel legal issues, and thought to herself, “How interesting!”
Grossly overthinking the matter, Judge Cannon ultimately issued a weirdly clever, creative ruling, leading legal commentator Chris Geidner to dub her “Trump’s best lawyer in years.” But the opinion was too clever by half—and just plain wrong—which is why the Eleventh Circuit made short work of it.2
The Trump v. United States debacle seriously damaged Judge Cannon’s reputation—and it also created a clerk problem. An incoming clerk from a top-three school, worried about a Cannon clerkship being a drag on their résumé, withdrew from the clerkship shortly after the Eleventh Circuit smackdown.
[I've left out a good deal of the chronology of Cannon's clerks]
Fast forward to June 2023. Judge Cannon gets United States v. Trump, Special Counsel Jack Smith’s prosecution of the ex-president for mishandling classified documents. It was a random assignment, meaning that the criminal case wasn’t given to her as a “related case” to Trump v. United States, the earlier civil case seeking the special master.
The documents case created immediate challenges for the Cannon chambers. It was a huge, high-profile prosecution, as well as a complex one, given the national-security issues. It generated a vast amount of additional work, and the chambers started to fall behind.
The documents case also required Judge Cannon’s three clerks to obtain security clearances, a consideration mentioned in yesterday’s post (update #13). One of the three clerks encountered delays in getting cleared, forcing the clerks who did have clearances to take on even more work—which they weren’t happy about. (A clerk without the requisite security clearance can’t work on the Trump case, but can work on other matters.)
As the months passed, the stress and workload increased in chambers. Judge Cannon became afflicted with an unfortunate combination of anxiety, from handling a matter of national importance, and insecurity, from never having run a case of this complexity. Understandably affected by all the pressure, the judge—whom her early clerks described as a wonderful mentor—started to change.
And not for the better. Here’s a January 2024 posting from the Top Law Schools (TLS) message board,3 describing Judge Cannon as a boss in the second half of 2023:
[G]enerally, she treats clerks (and the entire chambers staff) very poorly and tends to get angry to the point of screaming at them and talking to them in condescending ways. I know her courtroom deputy quit less than two years into the job.4
Expectation is basically that you don’t have a personal life during the clerkship and that work takes priority over anything else to the point that she controls what you do 24/7. This results in her micromanaging everything, and setting rules regarding when clerks are allowed to work on certain assignments, including an arbitrary rule that clerks can’t work on the daily filing for their cases (like drafting scheduling orders, orders granting motions for extension of times, etc.) until outside of in-office hours.
She frequently requires that clerks come into the office on weekends and federal holidays (including some major ones), even though she herself is there less than 1/4 of those days. And when she does require weekend or holiday work, she won’t let you know until last minute so if you bought a plane ticket, you’re out of luck. Even if she doesn’t mandate weekend work in the office, the deadlines she sets are so unrealistic that 9 times out of 10 you’re going to be working on a weekend just to turn in a not-great draft by the deadline (which only contributes to more yelling and screaming for it not being polished enough).
Average hours worked in a week are between 80-100, with 100+ hours a week not being uncommon. It’s definitely not a clerkship to take if you have a family
The Cannon clerkship experience wasn’t always like this.
Pre-Trump Judge Cannon was comfortable delegating to her clerks, which a busy trial judge must be able to do (appropriately, of course, with adequate supervision). Post-Trump Judge Cannon, increasingly worried about how her work product would fare under increased public scrutiny, thought she could ensure quality by getting more “into the weeds”—but micromanaging actually made things worse, not better.
[omitted more discussion of turnover among clerks]
So now the Cannon chambers is fully staffed. But it’s premature to declare that everything is hunky-dory. Note these facts, against the backdrop of Judge Cannon having one of the most high-profile, politically charged, complex cases in the country:
-- Three out of her four clerks have been with Judge Cannon for six months or less.
-- Only one of the current clerks, the clerk who started in August 2023, is there according to plan.
--- None of these clerks was in chambers in June 2023, when the Trump documents case arrived, i.e., they’ve all had to play catchup.
”I’d like to take this opportunity to clarify something I mentioned on Advisory Opinions: as I have previously written on multiple occasions, I do think Judge Cannon has some level of bias in favor of Trump, conscious or unconscious. Her opinion appointing a special master in the original civil case was so far off the map that it’s hard to explain otherwise, and some of her rulings in the current criminal case have taken a scolding tone toward Special Counsel Jack Smith and his team.
But I would add—quoting from my prior post, emphases added—that ‘it’s oversimplifying matters to dismiss all her rulings as purely the product of MAGA judging.’ Rather, I think that there are additional factors contributing to some of the weird rulings and frustrating delays in the case, including her lack of experience managing complex trials, her thinking too much like an appellate rather than trial judge, and problems managing her chambers. So yes, she has a pro-Trump bias—but to what degree, and to what extent it’s affecting her handling of the Trump documents case, can be debated.”