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Not long after special counsel Jack Smith filed a damning indictment against former President Donald Trump — accusing Trump of deliberately withholding classified federal documents that he had no right to possess in the first place — Smith received what could be the worst possible news about his chances of securing a conviction.
The case is assigned to Judge Aileen Cannon, a Trump appointee to the federal district court in southern Florida. Cannon, a fairly young judge who was confirmed to the bench after Trump lost reelection but before President Joe Biden took office, has come onto the national stage so far only once: for her extraordinary efforts to sabotage the Justice Department’s investigation into Trump’s possession of classified documents.
A panel of three appellate judges, two also appointed by Trump, eventually stepped in and neutralized this sabotage — in an opinion that identified about a dozen errors in her decisions. Eventually, a second panel of the United States Court of Appeals for the 11th Circuit ruled that she never had jurisdiction to interfere with the DOJ’s investigation in the first place.
That latter opinion — which was handed down by a panel that included two Trump appointees and Chief Judge William Pryor, a prominent figure in the conservative Federalist Society — labeled Cannon’s decisions favoring Trump “a radical reordering of our caselaw limiting the federal courts’ involvement in criminal investigations” and warned that Cannon’s approach “would violate bedrock separation-of-powers limitations.”
There’s no guarantee that Cannon takes the same cavalierly partisan approach to Trump’s criminal trial as she did to the FBI’s investigation. But it’s enough of a concern that her assignment to the trial, which her court says was made randomly using the ordinary process where judges are assigned to preside over criminal trials, immediately sparked alarm among a wide range of ideologically diverse lawyers.
Consider, for example, a warning offered by Orin Kerr, a center-right law professor at University of California Berkeley and one of the nation’s preeminent experts on Fourth Amendment law, who said Friday that Cannon’s past behavior suggests she may do “whatever she can to protect Trump.”
The Trump indictment allegations are bananas. With that said, if Judge Cannon is presiding, I'm not sure how much the facts will matter. Based on her decisions in the litigation over the warrant, Cannon may do whatever she can to protect Trump. And there's a lot she can do.
— Orin Kerr (@OrinKerr) June 9, 2023
Trump was arraigned before a magistrate judge Tuesday and pleaded not guilty to all 37 counts. But the case will be overseen by Cannon.
And make no mistake, if Cannon wants to, she could most likely place such a huge thumb on the scales of justice that it will be impossible for Smith to convince a jury to convict Trump no matter how strong his case may be. As Slate’s Mark Joseph Stern writes:
Cannon can try to rig voir dire [the jury selection process] to help the defense stack the jury with Trump supporters. She can exclude evidence and testimony that’s especially damning to Trump. She can disqualify witnesses who are favorable to the prosecution. She can sustain the defense’s frivolous objections and overrule the prosecution’s meritorious ones. She can direct a verdict of acquittal to render the jury superfluous. She can declare a mistrial prematurely for any number of reasons, including lengthy juror deliberations, and stretch out various deadlines to run out the clock.
All of this said, there is some case law suggesting that, in truly outlandish cases, the 11th Circuit may step in and replace a trial judge. In one 2006 case, for example, that appeals court removed a judge who twice botched the sentencing phase of a criminal trial. As the court wrote, “in light of the two reversals in this case and three other appeals in which we have reversed the same judge for extraordinary downward departures that were without a valid basis in the record,” replacing the judge was warranted. But judges are typically very reluctant to order one of their colleagues off of a case, and the legal standard governing involuntary disqualification of a judge is quite high.
So Cannon is likely to stay where she is. Here’s what that means for Trump’s potential trial.
Cannon’s previous rulings in Trump’s favor suggest that she is in the tank for the former president
Before we dive into the details of why Cannon may be unfit to hear Trump’s case, it’s important to note two factors that do not justify her removal. She is both a Republican and a Trump appointee, but these factors alone do not mandate recusal. And, indeed, there is a long history of federal judges ruling against the presidents who appointed them, including in cases that directly endangered the president himself.
So the fact that Cannon owes her job to Trump is not enough to stop her from presiding over his trial. In order to remove a judge, the 11th Circuit concluded in United States v. Torkington (1989), an appeals court must ask if the judge’s behavior on the bench suggests that they “would have difficulty putting [their] previous views and findings aside.” And even in such a case, the 11th Circuit is often reluctant to remove a judge.
That said, Cannon’s previous conduct in Trump’s case was egregious, and the 11th Circuit twice concluded that she committed multiple legal errors.
Cannon first got involved in this case after the FBI executed a search warrant in August 2022 at Mar-a-Lago, Trump’s Florida residence, and recovered more than 100 documents with classified markings — including one document that, according to the Washington Post, described “a foreign government’s military defenses, including its nuclear capabilities.”
Trump sued, claiming that this investigation must be put on pause, and asking Cannon to appoint a “special master,” a court-appointed official who is sometimes tasked with conducting complicated factual inquiries for the court. Trump wanted the special master to comb through the documents seized by the FBI to determine which of the seized documents should be returned to Trump.
Cannon agreed to appoint such a special master. More significantly, she also prohibited the Justice Department “from further review and use of any of the materials seized from Plaintiff’s residence ... for criminal investigative purposes” until the special master completed his review. That decision didn’t simply put this criminal investigation of Trump on ice, it also sabotaged a parallel intelligence investigation that the FBI conducted to determine if and how Trump’s retention of these classified documents harmed national security.
Eventually, the Justice Department brought the case to the 11th Circuit, which unanimously allowed the FBI to continue its investigations into the classified documents while the special master reviewed the remaining seized materials.
Of course, the Constitution’s Fourth Amendment does protect criminal defendants such as Trump from unreasonable searches of their property. No search warrants may be issued unless law enforcement can show that they have “probable cause” to justify a search, meaning that they have good reason to believe their search will uncover evidence of a crime. Law enforcement must present a sworn statement to a neutral magistrate which explains why they believe they have probable cause, and this magistrate must sign off on the warrant before a criminal suspect’s residence may be searched. The FBI complied with all of these obligations in Trump’s case.
Outside of these obligations, however, the 11th Circuit’s precedents rarely permit a court to interfere with an ongoing criminal investigation, and then only when the government has “displayed a callous disregard” for a suspect’s constitutional rights. Yet Cannon conceded in one of her rulings that “there has not been a compelling showing of callous disregard for [Trump’s] constitutional rights.” But she ordered the DOJ to halt its investigation into Trump anyway.
That alone, according to the 11th Circuit, “is reason enough to conclude that the district court abused its discretion in exercising equitable jurisdiction here.”
The 11th Circuit pointed to so many additional errors in Cannon’s decisions favoring Trump that it would be tedious to list them here. But there is one more problem in Cannon’s decisions worth highlighting. A major thrust of her decisions is that Trump was entitled to more protection than any other criminal suspect because he is a former president. This status, she claimed, placed “the stigma associated with” the FBI’s seizure of some of his property “in a league of its own.”
The 11th Circuit had no patience for this argument, holding in a December 2022 order that Cannon never had jurisdiction to hear Trump’s challenge to the search warrant, that the same law applies “no matter who the government is investigating.” This principle, according to the appeals court, flows from a 1794 Supreme Court decision holding that “our law applies ‘to all, without regard to numbers, wealth, or rank.’”
If another judge had committed similar errors, then perhaps those errors could be attributed to inexperience. Cannon is fairly young — she was still in her late 30s when Trump appointed her in late 2020 — and she’d been a judge for less than two years when she handed down her decisions favoring Trump.
But whatever else can be said about Cannon, she was hardly unfamiliar with Fourth Amendment principles governing search warrants when she departed so grievously from them. Cannon spent seven years as a federal prosecutor before becoming a judge, a job that would have required her to develop an intimate familiarity with the rules governing search warrants and seizures by law enforcement.
And yet, despite spending years developing expertise in this area of law, she still botched the Trump case so badly that two conservative panels of the 11th Circuit deemed her work unacceptable. That suggests that her errors may have been intentional, and not merely the product of ignorance.
How much power does Cannon have to protect Trump?
In the likely event that Cannon does not recuse herself from this case, and is not ordered to remove herself by a higher Court, she will have significant power to shape how fast this case proceeds, what evidence is presented to the jury, and who sits on that jury. These rulings often involve subtle decisions that are difficult to challenge on appeal, and that may not even have much impact on the case individually — even if the collective impact of a long series of decisions against the prosecution could destroy their case.
And even if Smith’s legal team does eventually convince an appeals court to reverse any of Cannon’s decisions, appellate courts are normally reluctant to hear “interlocutory” appeals — challenges to a trial judge’s decision that are heard before that judge is finished with the case. Many of Cannon’s errors could not even be reviewed until after Trump’s trial is over.
To give a sense of just how much Cannon could skew this trial in Trump’s favor if she wanted to, consider how jurors are screened in federal court.
Before any jurors are seated, they will be questioned by counsel on both sides of the case, and potentially by the judge, in a process known as “voir dire.” One of the most important purposes of this process is to screen out jurors who may be biased or otherwise unable to evaluate the allegations against a defendant impartially.
As a general rule, a potential juror might be removed from a jury pool for two reasons. Both the prosecution and the defense have a limited number of “peremptory” strikes, which can be used to remove a juror for virtually any reason. Additionally, if a juror’s statements during voir dire suggest that they may not be impartial, either side’s lawyers may ask the judge to remove a juror “for cause.”
In a normal case, for example, the defense might ask for a juror to be removed for cause if the juror demonstrates prejudice toward people who share the defendant’s racial or religious background. The prosecution might ask for a juror to be removed for cause if that juror testifies that they’ve had so many negative interactions with the police that they are inclined not to trust any testimony by a police officer.
But the Trump prosecution is obviously not a normal case, and the judge presiding over it will need to make delicate decisions about which potential jurors can be impartial about one of the most famous and polarizing individuals on the planet. Suppose that a potential juror testifies that they voted for Trump twice and once attended a Trump rally, but that they believe they can still be impartial. Should this juror be removed for cause? What about a Biden voter who donated to the incumbent president’s campaign? Or a juror who testifies that they are a regular Fox News fan? Or a juror who marched in a protest against Trump’s immigration policies?
Trial judges normally have a great deal of discretion to decide which jurors may be included and which jurors must be excluded. So, if Cannon presides, there’s a real risk that she might try to stack the jury with sympathetic jurors. Smith’s legal team could still use their peremptory strikes to remove MAGA jurors, but they will have a limited number of those strikes.
And Cannon would not even need to stack the entire jury to sabotage Smith’s case against Trump, if she was so inclined. The Supreme Court held in Ramos v. Louisiana (2020) that the Constitution “requires a unanimous verdict to convict a defendant of a serious offense.” So Cannon would only need to seat one MAGA juror to ensure that, at the very least, even the strongest possible case against Trump will end in a hung jury and a mistrial.
Voir dire, moreover, is just one small part of a trial. During the rest of the trial, the presiding judge will rule on which evidence can be introduced and which evidence must be excluded, what questions lawyers may ask witnesses and which questions are forbidden, and which witnesses are even allowed to testify.
And, even if Trump is convicted despite potentially biased rulings from Cannon, she will have the first crack at sentencing Trump — and the Supreme Court held in Gall v. United States (2007) that appeals courts must review a trial judge’s sentencing decisions “under a deferential abuse-of-discretion standard.” That means any lawyer challenging a trial judge’s sentencing decision faces a difficult battle.
All of this should come with the caveat that, perhaps, Cannon learned her lesson after she was smacked down twice by an appeals court, and maybe she will be more careful about adhering to the law during Trump’s trial. But her conduct in the litigation over the Mar-a-Lago search warrant should not fill anyone with hope that she will suddenly decide to be unbiased and impartial.
Can Cannon be removed from this case?
There is a chance that Cannon could be removed from the case if Smith seeks to disqualify her, or if the 11th Circuit decides on its own to remove her on appeal. As that court said in the Torkington case, such disqualification “is appropriate where the trial judge has engaged in conduct that gives rise to the appearance of impropriety or a lack of impartiality in the mind of a reasonable member of the public.”
That said, the 11th Circuit has typically required a judge to repeatedly engage in behavior that casts doubt on their impartiality before removing that judge. In Torkington, for example, the trial judge “stated at various times that he felt the taxpayer had little interest in this type of suit, that this prosecution was ‘silly,’ and that it was a waste of the taxpayers’ money.” He also suggested that the prosecution might arise from a “vendetta” against the defendant.
Similarly, in United States v. Martin (2006), another case where the 11th Circuit disqualified a trial judge from continuing to hear a criminal case, the appeals court did so only after it had twice reversed the trial judge’s sentencing decisions — and only after the same judge had been reversed in three other cases for handing down lenient sentences that the appeals court deemed “extraordinary.”
There is no doubt Smith’s team could write a well-reasoned brief, relying on cases like Torkington and Martin, that would make a strong case for disqualifying Cannon. And if the right 11th Circuit panel is assigned to hear a request to remove Cannon, that panel might agree she must be recused.
But the 11th Circuit is also a conservative court — seven of its 12 active judges were appointed by Republicans and six were appointed by Trump. And the standard for disqualifying a judge is very high. Realistically, it is difficult to know how the appeals court would rule on a request to disqualify Cannon. A competent judge could write a decision supporting either outcome.
All of this said, I would hope that any judge asked to review whether Cannon should preside over this case would pay particular attention to one line in Torkington, where the court said that removing a trial judge from a case is sometimes necessary because “the judicial system has the obligation of preserving public confidence in the impartial and fair administration of justice.”
The trial of Donald Trump, a longtime celebrity and former president, is likely to be one of the most closely watched legal proceedings in American history. Every decision the trial judge makes will be scrutinized by a small army of attorneys, many of whom will be nationally prominent experts such as Kerr. Numerous media outlets (including the one you are reading right now) also employ lawyers with considerable expertise in federal courts, who will shine a light on every error committed by the judge in Trump’s case.
The 11th Circuit, in other words, needs to ask itself whether it can trust Aileen Cannon to speak for the federal judiciary in one of the most closely watched tests of its legitimacy that the third branch of government will ever face.
Update, 3:30 pm ET: This article has been updated with news of Trump’s arraignment.
