11 June 23
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Cannon, a Trump appointee, gained notoriety while presiding over Trump’s attempt to halt the classified documents investigation in 2022. Following the search of Mar-a-Lago, Trump’s lawyers filed a complaint alleging that the search was illegitimate and unconstitutional; they demanded the appointment of a special master and, in the meantime, a freeze on prosecutors’ review of seized materials. In a calculated act of judge shopping, the case was assigned to Cannon, who leaped at the opportunity to prove her fidelity to the man who’d appointed her and, perhaps, audition for a future Supreme Court seat. Trump’s lawsuit amounted to pure gibberish, a glorified Truth Social post that alleged a Democratic conspiracy. So Cannon promptly encouraged his lawyers to rewrite the suit so it sounded marginally less asinine. She then issued an order prohibiting the government from “further review and use of any of the materials” seized from Mar-a-Lago “for criminal investigative purposes.”
This command marked the first time in the history of the republic that a federal judge had claimed the power to stop a pre-indictment criminal investigation into a suspect. Cannon’s overreach provoked genuine shock in legal circles and fear in the intelligence community, as it effectively blocked officials from assessing the seized documents for national security risks. (Her order reflected a profound misunderstanding of national security damage assessments.) A right-leaning panel of the U.S. Court of Appeals for the 11th Circuit—which included two Trump appointees—soon stayed this portion of her decision, highlighting its “chilling” effect on fundamental “national-security duties.”
But Cannon wasn’t finished. She agreed to Trump’s request for a special master and appointed Raymond Dearie, a well-respected federal judge. After Dearie tried to bring some discipline to the case, though, Cannon immediately ran interference for Trump. She overruled an order that would’ve required the former president to either disavow or stand by previous claims that FBI agents planted evidence at Mar-a-Lago. She spared him the burden of lodging specific objections to the review of individual documents, which would have revealed the bogus nature of his claim to executive privilege. And she extended deadlines to help Trump drag out the special master’s review for as long as possible.
The madness finally ended when a panel of the 11th Circuit—made up of two Trump appointees and the ultraconservative William Pryor—ruled that Cannon had no authority to hear Trump’s lawsuit in the first place, rendering every one of her orders null and void. It was one of the most humiliating appellate smackdowns in recent history, a total demolition of literally every action that Cannon had taken from the outset of the case. The 11th Circuit accused Cannon of attempting “a radical reordering of our caselaw” that violated “bedrock separation-of-powers limitations.” And it directed her to relinquish control over the case.
Now fast-forward to today. Cannon has been assigned to handle at least the initial phases of Trump’s federal indictment in Florida. Her name appeared on the summons sent to the former president, as did Bruce Reinhart’s, the magistrate judge who signed off on the Mar-a-Lago search warrant. (Magistrate judges may conduct preliminary proceedings in a criminal case, like authorizing a warrant, but it’s unlikely that Reinhart will play a major role here.) Typically, federal district court judges are assigned cases randomly, though the court may transfer a case to a specific judge who has prior experience with the matter. So, perhaps Cannon’s (calamitous) oversight of the Mar-a-Lago search dispute gave her dibs on this indictment. Cases are also reassigned based on workload to ensure that there’s a roughly even distribution among active judges. All of this means that we don’t really know why Cannon was initially assigned the case, and we don’t know if she will keep it. We can be fairly confident, though, based on her history, that she will do everything in her power to keep it to protect her benefactor, who is clearly in immense legal danger from this case.
Smith, for his part, has the option of requesting a different judge; 11th Circuit precedent allows reassignment when the presiding judge appears unable to put “previous views and findings aside.” (This is a nice way of saying that they’re in the tank for the defendant.) Trump would surely fight such a request, and it’s impossible to say where the 11th Circuit would come down.
Imagine, though, that Cannon does preside over this case. She has infinite tools at her disposal to thwart the prosecution at nearly every turn. Big swings, like tossing out the whole case—a very real possibility in her courtroom of chaos—can be appealed and overturned. But at every step, there are opportunities for sabotage. Cannon can try to rig voir dire 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. Many of these procedural moves could not be appealed until the proceedings have drawn to a close; appeals courts do not referee every little dispute in a jury trial as they happen. Cannon will be in control.
That should be a frightening prospect for Smith. Cannon has already revealed her profound bias in favor of the president who appointed her, breaking a series of bedrock rules to help him escape the classified documents probe. Now she seems to have gotten a second bite at the apple, a chance to manipulate court procedures to assist Trump and subvert Smith at every turn. Let’s not pretend as if it’s a mystery whether she will; her name is already synonymous with MAGA-style judicial corruption. The simplest way to put it is that if Cannon remains assigned to this case, Trump will not be convicted, no matter how damning the evidence. That conclusion is not defeatist or cynical; it is a mere acknowledgment of the reality that Republicans have created by stacking the bench with venal mediocrities like Aileen Cannon.
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