Clerking For Judge Cannon: A Behind-The-Scenes Look

A tale of two clerkships: it was the best of times, it was the worst of times.

The Alto Lee Adams Sr. U.S. Courthouse in Fort Pierce, Florida, home to the chambers of Judge Aileen M. Cannon (photo by Joe Raedle via Getty Images).

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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. In the words of Jesse Panuccio, a prominent Florida litigator and current partner at Boies Schiller Flexner, “She had a sterling résumé and great reputation.”

When rating judicial nominees, the American Bar Association (ABA) generally wants 12 years of experience for district judges. Cannon just met that mark, and the ABA rated her “Qualified” (with a minority of the panel rating her “Well Qualified,” but the majority rating controls).

Confirmed by the Senate in November 2020—by a bipartisan vote of 56-21, with the support of 10 Democrats (23 senators were absent or otherwise didn’t vote in that post-election, lame-duck session)—Cannon began her judicial service that month. She was only 39 years old.

Her early years as a judge were uneventful. Based out of the satellite courthouse in Fort Pierce, around two hours north of Miami, she presided over only four jury trials, none lasting longer than five days. Based on interviews with lawyers who appeared before her, the New York Times described her as “generally competent and straightforward,” while the Washington Post reported that she was “polite and process-oriented… asking a lot of questions, while making sure litigants can fully air their views.”

Her judicial career was off to a perfectly fine start. And her early law clerks had positive experiences.

“How you enjoy your clerkship with Judge Cannon will be shaped by your priors,” one source told me. “If you get easily stressed or try to get through life with minimal work, you’ll find her overly demanding and domineering. But if you’re used to adversity, being in difficult situations, and making hard calls, you’ll do well. You’ll find her to be a tough boss, but one who gets your best work out of you.”

A former clerk I quoted in yesterday’s post about Judge Cannon (update #9) said basically the same thing: “I had a wonderful experience clerking for Judge Cannon. Through her mentorship and guidance, I developed in a way that I did not know I was capable of. My time in chambers with the Judge prepared me to overcome any professional challenge I might come across.”

“My clerkship with Judge Cannon was an invaluable learning experience,” said another early clerk. “On a professional level, she is thoughtful and hardworking. On a personal level, she has been a caring and supportive mentor to me. I am grateful that I had the opportunity to work for her.”

Everything was going fine for Judge Cannon. 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.

This left Judge Cannon with a clerkship slot to fill for the 2023-2024 judicial year. So she asked one of her 2022-2023 clerks, whom I’ll call “Kari,” to extend her one-year clerkship into a two-year position.

Kari said yes, but on the condition that she work a fixed number of hours. She was going to be the mother of a very young child by the start of that second year, and she didn’t want to be working the longer hours of her first clerkship year. Not having much leverage, Judge Cannon agreed. Upon information and belief, Kari agreed to work a full-time schedule, say 40 hours a week, but no more than that.

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.)

In July 2023, a clerk whom I’ll call “Mary” started in chambers—and wasn’t thrilled to be there. Having accepted the clerkship before Judge Cannon became (in)famous for her handling of the first Trump case, Mary was unhappy about how the credential value of her clerkship had declined post-acceptance, along with Judge Cannon’s reputation. She was also annoyed by Judge Cannon’s approach to training, which requires clerks to come into chambers a few days early, on an unpaid basis, to learn her case management system. Suffice it to say that Mary’s clerkship started off on the wrong foot. [Note the UPDATE added below (3:25 p.m.).]

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. Take the comment about her “micromanaging.” It contrasts sharply with this testimonial from one of her early clerks: “Judge Cannon had a lot of confidence in our abilities, and she gave us a lot of responsibility in chambers, which prepared us to be effective lawyers in any substantive practice area.”

These sound like two different clerkships with two different judges, “Pre-Trump” Judge Cannon and “Post-Trump” Judge Cannon. 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.

As summer turned to fall, the holdover clerk from 2022-2023 who had agreed to stay on for a second year, Kari, was increasingly unhappy. Back from parental leave, with a baby at home, she was supposed to be working fixed hours, per her agreement with Judge Cannon. But because of the crushing amount of work—which Kari had to perform a disproportionate amount of, thanks to the aforementioned security-clearance issues of a co-clerk—she was working far more than 40 hours a week.

In October 2023, after a year and two months in chambers, Kari quit. She wasn’t getting the fixed hours she had bargained for, she wanted to spend more time with her baby, and the overall environment in chambers was increasingly unpleasant. (Her LinkedIn profile does not show any subsequent employment.)

A replacement clerk for Kari started later that month. But as I noted yesterday, such unanticipated, mid-year transitions can really throw off the work of a chambers. Successor clerks need to get up to speed, on both chambers procedures and the substance of cases—which is very time-consuming, especially in complex cases like the Trump prosecution.

As fall turned to winter, conditions in chambers continued to worsen. Mary, whose clerkship had gotten off to a bad start, was working 80-hour weeks and having interpersonal conflict with the judge, whom she described to friends as “mean.”

Mary began plotting her escape. She reached out to the D.C. law firm where she had been a summer associate and asked if they would take her on if she quit the clerkship; the firm said yes. She reached out to the prominent conservative circuit judge with whom she already had a future clerkship lined up, to see if she’d still have a place in that judge’s chambers if she quit on Judge Cannon; the circuit judge also agreed.

The responses of her firm and future judge gave Mary the reassurance she needed that her career could survive the damage from quitting a clerkship after six months—which, as previously discussed, can be considerable. As Professor Eric Segall put it after yesterday’s news broke, “Clerks never quit. That’s all.” [Note the UPDATE added below (1:38 p.m.).]

In December 2023, Mary quit. Per her LinkedIn profile, she started at the firm in February.

In January 2024, two new clerks arrived in chambers—a replacement for Mary, plus a temporary clerk. This took the number of clerks up to four, where it is today. As noted in yesterday’s story (update #12), judges who need extra help in chambers—such as judges with super-complex matters like the Trump case, or judges overseeing multidistrict litigations (MDLs)—can get extra clerk help on a temporary basis.

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.

All the unexpected departures and arrivals of the past six months have surely contributed to the backlog and delays in the case. I also wonder whether all four clerks have the security clearances they need to work on the Trump case. All in all, it’s not a great situation.

So where does this leave matters? Judge Cannon still has the Trump documents case. Numerous motions in the case remain pending. We still don’t have a trial date, even though both the prosecution and the defense have stated that they believe the trial can start this summer.

And there’s no clear path to any of this changing. I believe the prospects for getting Judge Cannon removed from the case are greatly exaggerated (especially since Jack Smith has given no indication that he plans to seek such relief).

Aileen Cannon enjoyed a remarkable rise through the legal profession. She became a federal judge before age 40. Her judicial career got off to a perfectly solid start. Her first law clerks liked and respected her.

And then came the Trump cases.

Remember the saying, “Everything Trump touches dies”? Add Judge Aileen M. Cannon to the long list of people who have come into contact with Donald J. Trump and whose reputations—and lives—will never be the same.⁵

Ed. note: As my regular readers know, I believe strongly in accuracy, so I frequently update posts with comments and corrections (and timestamps indicating when the update was added, because I also believe in transparency). So for my newsletter subscribers who read this post in email form, I urge you to go to the web version and refresh for the latest updates. Yesterday’s post about Judge Cannon, for example, has 14 updates—so if you read only the original version, you might want to go back and look at the updates.

UPDATES:

1. A current law clerk (not to Judge Cannon) made this point to me, which I found interesting (and view as a fair rejoinder to Professor Segall’s “clerks never quit” point):
   
   ”I’m surprised by how surprised people are that the experience was bad enough for clerks to quit. Clerks do quit, half of all judges are below-median employers (by definition), and the median is not necessarily that high. Regarding what Aliza Shatzman of the Legal Accountability Project is trying to do, I think it would gain even more traction if people really knew how widespread the problem was. Hopefully your reporting can contribute to that. I am completely making this up, but I bet if you were to ask law professors what percentage of clerks quit a clerkship, they’d say less than 1 percent. I would put the actual number at 5 percent or more based on my peers, forums, word of mouth, etc.” [1:38 p.m.]

2. Here’s a thoughtful comment I received from an appellate lawyer who was nominated for a district-court judgeship:
   
   ”Interesting post and investigation. To begin with, I relate a little bit in that when I was nominated to the district court, one of my great fears was that if confirmed I would have a tendency to think too much like an appellate lawyer and not enough like a practical trial judge. I like to think that by having more seasoning than Judge Cannon and much more experience actually consulting during trials, I would have handled things better than Judge Cannon, but I do empathize with her given our shared backgrounds. I don’t know her personally, but I know many people who do know her, and I don’t think she is biased. I think she is trying her best but is just being, as you suggest, a too-smart appellate lawyer not grounded by reality.” [3:06 p.m.]

3. At least two sources have informed me that Judge Cannon’s approach to training—having new law clerks come into chambers in advance, for a few days or even a week, unpaid—is the approach of many (and possibly all) judges in the Southern District of Florida. [3:25 p.m.]

4. I’d like to highlight something I wrote in my latest Judicial Notice legal news roundup:
   
   ”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.” [4/4/2024, 3:30 p.m.]

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1. Ed. note: The footnotes in this post will be interesting to legal nerds, but other readers can afford to skip them. Most of the chambers drama that many people are seeking is in the body of the post.

Recall that during her time as an assistant U.S. attorney (AUSA), Cannon spent most of her time on appellate work, i.e., defending convictions and sentences on appeal. This explains why she had only four jury trials as a federal prosecutor, a low number for a seven-year tenure. Even in an age of diminishing trials, most trial AUSAs have at least two or three trials a year—so after seven years, a trial-level AUSA probably would have had 15 or more trials, roughly four times as many as Cannon.

My last legal job before becoming a writer was also working as an appellate AUSA—in the District of New Jersey, under then-U.S. Attorney Chris Christie (my most recent podcast guest)—and I can’t emphasize enough the difference between trial and appellate work. Appellate work has its virtues. It’s intellectual and you get to write a lot, so it attracts smart lawyers like Aileen Cannon with excellent academic credentials. But being an appellate “nerd,” as I once was, is poor preparation for being a trial judge.

Reading the trial record to defend a verdict on appeal is a far cry from creating that record yourself as a trial lawyer, on your feet in a courtroom, arguing to a jury. And the pace of appellate work is much slower, almost leisurely; it doesn’t equip you to deal with the torrent of cases that flows through a trial court.

I like to think I was a good appellate AUSA, but I would have been a terrible trial judge—not because I’m unintelligent or lazy, but because working as an appellate AUSA just isn’t a good professional background for being a trial judge. And I think Judge Cannon is similarly struggling because her professional background, while distinguished, isn’t a good fit for her current role. (She probably would have been a fine appellate judge, although maybe prone to go off on the occasional frolic and detour—like a Judge Guido Calabresi (2d Cir.), but from the right.) [Note the UPDATE added above (3:06 p.m.).]

2. I also blame Judge Cannon’s overthinking for the bizarre order she issued on Monday night about jury instructions. By treating these questions as a Borkean “intellectual feast,” instead of practical issues to be resolved quickly and decisively, she’s exhibiting an appellate judge’s tendency to overcomplicate things, when as a trial judge she needs to streamline and simplify. So again, she’s very smart; she’s just deploying her considerable intelligence in ways that defy common sense.

3. I feel comfortable quoting this TLS posting because (a) my own sources confirm both its overall gist and several of its specific claims, such as the 80-hour weeks and the departure of the deputy, and (b) I offered both the Southern District of Florida Public Information Office (PIO) and the Cannon chambers the opportunity to comment on it, which they didn’t take. The S.D. Fla. PIO stated that the court “cannot comment on HR-related matters” (update #14 in yesterday’s post), while the Cannon chambers did not respond.

4. I have confirmed the departure of Judge Cannon’s courtroom deputy with two other sources, both lawyers in South Florida. In addition, a commenter at David Oscar Markus’s SDFLA Blog claims that she lost her court reporter, but I have not independently verified this (as I have with the deputy).

The news about the deputy didn’t surprise me, since I had previously heard rumors about non-clerk employees also having issues with Judge Cannon. I hinted at this in yesterday’s post: “Additional information about other personnel issues in her chambers—possibly involving employees other than clerks, such as judicial assistants or courtroom deputies—could emerge.”

5. I acknowledge that a significant amount of the fault for Judge Cannon’s plummeting reputation rests on… Judge Cannon. But as discussed above, I think the “she’s simply a partisan hack” narrative oversimplifies matters, even though I believe she has a bias in favor of Trump. (Or, maybe to put it more kindly, she gives frivolous arguments from his team far more consideration than they deserve—and perhaps her defenders would say that she tries to give all arguments, even weak ones, as much consideration as possible.)

I also think it’s fair to say that if she had never gotten the Trump cases, today she would probably be what she was before they came along: a well-respected, well-liked member of the South Florida legal community, with happy current and former clerks.