Trump Looks Doomed. An Infamously Pro-Trump Judge Could Save His Bacon.

Federal prosecutors shocked political pundits and legal analysts alike with their damning criminal indictment of former President Donald Trump for allegedly mishandling sensitive national security documents.

The details were stunning. The charging document, released Friday, cited a recording of Trump showing a roomful of people without security clearance a military attack plan he called “secret information.” It contained a now-infamous photograph of sensitive intel documents piled in a bathroom next to a toilet. Prosecutors alleged that Trump literally took the nation’s nuclear secrets down to his beach club, and then hosted events featuring tens of thousands of guests.

Pretty bad for Trump, everyone said. Then came the rub: Trump drew the most infamously pro-Trump judge in all of south Florida. If anything can save his bacon from this otherwise-doomed hellscape of a legal inferno, Judge Aileen Cannon just might find a way. And she’ll have plenty of authority to do so.  

“The district judge has tremendous power over a criminal case from beginning to end,” explained Harry Sandick, a former prosecutor for the Southern District of New York. 

Trump’s case will be overseen by Cannon, 42, who shocked lawyers and experts last year by bending over backwards to deliver favorable rulings to Trump during a civil legal battle over the FBI’s search of his Mar-a-Lago estate in August 2022. 

Back then, lawyers watching her decision-making process ran out of adjectives to describe Cannon’s baffling and disturbing decisions. 

In September, Judge Cannon froze the review of files seized by the FBI and appointed an independent legal expert to look at them first. Lawyers called that decision a “nutty,” “laughably bad,” “nonsensical legal pretzel.” She fretted openly about the “stigma” and “reputational harm” that the investigation, and a possible indictment, could cause Trump. She overruled the legal expert, known as a Special Master, whom she herself had appointed to review the files when he tried to get Trump to clarify his position in the case and speed up the process. 

Judge Cannon was eventually slapped down by an appeals court, which issued a blistering decision saying she never had the authority to intervene in that case in the first place. In the meantime, she showed no sense of shame about all the incoming criticism she received.

Now, she’s back. And her assignment to this case represents a glimmer of light for Trump in an otherwise dark legal outlook. 

“I think the Cannon draw is actually a serious blow to the prosecution,” Paul Rosenzweig, a former prosecutor, expert on presidential investigations, and member of the Ken Starr investigation into former President Bill Clinton, told the New York Times. “If this were a normal person and a normal case, you’d be talking to your client about pleading guilty.” 

Trump was charged with 37 criminal counts, for allegedly violating the Espionage Act and obstructing justice, by Special Counsel Jack Smith, who was appointed by Attorney General Merrick Garland last November. 

Trump has declared himself an “innocent man,” and he is expected to plead not guilty at his arraignment in Miami federal court on Tuesday. From here on, however, Judge Cannon, a longtime member of the conservative Federalist Society, will have lots of ways to tilt the board in Trump’s favor. 

Judge Cannon could slow the case down, and help ensure that a trial only takes place after the November 2024 presidential election. 

She could approve the selection of jurors who show partiality towards Trump — in a city where Trump enjoys broad support from Latino voters who fear that his Democratic rivals might bring socialism.  

She could disqualify the prosecution’s most important witnesses, or refuse to admit damning evidence. She could grant Trump’s team advantages and deny motions by the prosecution. 

She could even dismiss the case completely. Depending on the circumstances, prosecutors might not be able to do anything about it. 

“The judge can dismiss a case on limited legal grounds before trial, in which case the government can appeal,” Sandick said. “However, if the judge dismisses the government’s case mid-trial, after the government presents its case but before it goes to the jury on the basis that the government has not proved its case, the government cannot appeal from this dismissal.” 

Dismissing the case would be widely seen as an extreme move, especially given all the skepticism about her impartiality. But the question becomes: Would Judge Cannon care? 

“Most of all, if the district judge makes errors during the trial that favor the defense, and the case ends in an acquittal, there is no appeal for the government from these errors — the case is over and double jeopardy bars a second prosecution,” Sandick said. “The judge also has very broad discretion at sentencing, which is only lightly reviewed by the Court of Appeals.”

Judge Cannon was randomly assigned to the case, and will only be removed if she decides to recuse herself, the chief clerk of the federal court system in the Southern District of Florida told the Times over the weekend. 

It remains possible that Judge Cannon may feel that the criticism she received — from both outside observers, and from the appeals court in her own 11th Circuit — may be enough to cause her to change course.