Aileen Cannon Is Who Critics Feared She Was

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One year ago, when former President Donald Trump was indicted on charges related to his hoarding of classified documents, the case was randomly assigned to Aileen Cannon, a federal judge for the Southern District of Florida.

Cannon’s selection immediately stirred up worries. She had little trial experience, having been appointed to the bench at just 39. She was an appointee of Trump himself. And she had already raised concerns with her rulings in favor of Trump in a precursor to the case, which were later reversed by a sharply critical appeals court. These objections might have been premature: Interpreting a judge’s mindset, and assessing her shortcomings, from the outside can be difficult. But after a year of action—and, perhaps more important, inaction—from Cannon, it seems that many of the worst fears about her were not just well founded but understated: Her track record in the case has been extremely favorable to Trump, to a degree that undermines any faith in her ability to adjudicate it fairly going forward.

The latest astonishing development is a New York Times report yesterday that two other federal judges in Florida’s Southern District sought to persuade her to step aside from the case and let another jurist take it. One colleague argued to Cannon that it would be better for a judge in Miami, rather than her satellite Fort Pierce courthouse, to deal with the case, in part because the Miami courthouse has a facility for sensitive documents, the paper reported. When Cannon demurred, the chief judge of the district called her and argued that her reversed decision earlier meant that her having this case would look bad. She again declined to hand it off.

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Whether Cannon’s colleagues were concerned about inexperience or bias is not clear from the reporting, but what is striking is that they seem to have reached the same conclusion that many outsiders did at the time and later: Cannon has no business presiding over the case.

Comparing Trump’s different indictments is dicey, and two other cases against Trump, which accuse him of subverting American democracy itself, have overshadowed the documents case. But in this case, Trump stands accused of something very dangerous—extremely careless handling of the nation’s most sensitive secrets. He allegedly tried extensively to hide documents from the government, even after a subpoena. Nor does much doubt exist about whether he had the material, because FBI agents recovered it in a search of his Mar-a-Lago residence in August 2022. No felony case against a former president is simple, but the basic outlines of this one are straightforward and quite serious.

After the documents were recovered, Cannon ruled that prosecutors couldn’t review the files until a special master had filtered them—a ruling that would have benefited Trump by freezing the investigation and potentially discarding evidence. “This would seem to me to be a genuinely unprecedented decision by a judge,” Paul Rosenzweig, a former federal prosecutor and an occasional Atlantic contributor, told the Times then. But an appeals court overturned Cannon, saying her approach “would violate bedrock separation-of-powers limitations.”

The investigation continued, and an indictment followed, but Special Counsel Jack Smith had a stroke of bad luck when Cannon randomly drew the assignment. That’s turned into a bad-luck streak, as Cannon has repeatedly moved back deadlines. The trial was once scheduled to begin in May; now no tentative date even exists. She’s also ruled against prosecutors again and again.

In March, she told both sides to submit proposed jury instructions, an odd suggestion so early in the process. Moreover, her order implied that she was taking seriously a Trump argument that the Presidential Records Act allowed him to retain some “personal” documents. In a frustrated response, Smith’s team called the theory “pure fiction” and asked for a quick ruling on the question. She replied that the request was “unprecedented and unjust.”

In May, she delayed a deadline for major filings. Later that month, after Trump falsely claimed that the FBI had planned to assassinate him in the Mar-a-Lago search, prosecutors asked that he be barred from making statements about law enforcement. Instead, Cannon threatened to sanction them for not first conferring with defense lawyers. And earlier this month, she removed a paragraph from the indictment, saying it was not connected to any specific charge against Trump.

Today, she will hear arguments over whether Smith’s appointment as special counsel was unconstitutional, a strain of argument that other courts have long rejected. She has also agreed to hear arguments from third parties on the question, which is highly unusual in trial courts. Even when Cannon has ultimately rejected defense claims, she has first held hearings on matters that few judges are willing to entertain.

The case is crawling forward at the same time that the Supreme Court has been dilatory in ruling on Trump’s argument that he should be immune to prosecution for acts taken as president—a claim that could upend his federal indictment for subverting the 2020 election. And just as no mechanism exists to speed up the justices, prosecutors have little recourse with Cannon. They don’t have any of the hard evidence that would justify a recusal, and though they might be able to successfully appeal, that takes time—and Smith is on the clock. Already, voters seem unlikely to get a ruling before they cast ballots this fall; the question now is whether Trump wins and is able to have the case against him dismissed.

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If Smith’s filings show a rising irritation, outsiders who have no need to be polite have not been. “The fact these motions are even being entertained with a hearing is itself ridiculous,” the national-security lawyer Bradley Moss told CNN. “The magnitude of the legal mistakes that are happening is weird. They’re always in the same direction, right? The legal mistakes are always Trump-favorable,” the University of Texas law professor Lee Kovarsky told New York. “It’s clear that she is going in a ridiculous direction,” Nancy Gertner, a retired federal judge, told Politico. The attorneys Dennis Aftergut and Laurence Tribe wrote in Slate that Cannon “is quietly sabotaging” the case. “Judge Cannon is proving that she is not fit for this moment,” the former CIA attorney Brian Greer wrote in the Times.

That these commentators would be critical of Cannon is perhaps no surprise—they include Democratic appointees, Trump critics, and federal prosecutors, all people inclined to be sympathetic to Smith. What affirms their concerns is that Cannon’s colleagues—people who intimately know the court, the law, and the judge herself—evidently agreed.