The Right-Wing Judge Who Could Tank the Most Slam-Dunk Case Against Trump

Amid all the excitement generated by the indictments against Donald Trump in Washington, D.C., and in Fulton County, Georgia, for election subversion, it’s easy to lose sight of the Mar-a-Lago documents case, which is set for trial next May. But of all Trump’s legal woes, that case is the only one that looks like a slam dunk.

Trump stands accused of committing 40 felonies for absconding from the White House with a trove of classified and top-secret papers, stashing them at his Palm Beach golf resort, and refusing to return them to the federal government on demand. Two other defendants—Walt Nauta, Trump’s longtime valet; and Carlos de Oliveira, the resort’s property manager—are accused of committing some crimes jointly with Trump and others on their own.

Unfortunately, there is one big problem facing Special Counsel Jack Smith’s team in the Sunshine State: The trial will be presided over by District Court Judge Aileen Mercedes Cannon, who may just be in the metaphorical tank for the former President.

Given the broad authority of federal trial judges and her obvious pro-Trump bias, Cannon will be uniquely positioned to help the ex-President as the case unfolds.

Cannon, who was born in Colombia and grew up in Miami, was nominated by Trump in May 2020 to serve on the United States District Court for the Southern District of Florida. She was 39-years-old, relatively young by federal judicial standards.

Cannon was confirmed by the Senate on November 12, 2020, nine days after Trump lost the presidential election, despite having only four minor jury trials on her resume as a practicing attorney. Her scant record as a published author at the time of her nomination included a series of human-interest pieces she wrote as an undergraduate for El Nuevo Herald, a Miami-based Spanish-language daily newspaper. Among the topics she covered were prenatal yoga, the health benefits of tomatoes, and flamenco dance.

By all appearances, Cannon grew more serious in law school at the University of Michigan, joining the Federalist Society and establishing herself as a staunch conservative. She served as an assistant U.S. attorney in southern Florida from 2013 to 2020, and in that capacity, caught the eye of the Trump Administration as a worthy candidate to add to the growing cadre of right-wing judges the ex-President had appointed.

Once enrobed, Cannon was assigned to a courtroom in Fort Pierce, north of West Palm Beach. Under normal circumstances, she would have remained under the radar for years, handling a challenging but standard docket of civil and criminal litigation. The FBI’s search of Mar-a-Lago on August 8, 2022, changed that trajectory in a flash.

Cannon was assigned to hear a highly unusual civil lawsuit Trump’s lawyers filed on August 22, seeking an emergency protective order to block the government from indicting Trump until the propriety of the search could be reviewed by an independent arbiter known as a “special master.” Suddenly, she found herself in the national spotlight.

To the shock and dismay of many legal observers, Cannon ruled quickly in Trump’s favor, issuing an order on September 5, appointing a special master, and reasoning that Trump was entitled to be treated differently than other criminal suspects in order to avoid the “reputational harm” that could have resulted from a hasty indictment. “As a function of Plaintiff’s former position as President of the United States,” Cannon wrote, “the stigma associated with the subject seizure is in a league of its own.”

At the Special Counsel’s request, the 11th Circuit Court of Appeals quickly intervened and rebuked Cannon in a stinging reversal, holding:

The law is clear. We cannot write a rule that allows any subject of a search warrant to block government investigations after the execution of the warrant. Nor can we write a rule that allows only former presidents to do so. Either approach would be a radical reordering of our case law limiting the federal courts’ involvement in criminal investigations. And both would violate bedrock separation-of-powers limitations.

Incredibly, now that Trump has actually been indicted, Cannon is once again presiding, apparently impervious to demands that she recuse herself due to the appearance of bias. According to the district-court clerk, she was randomly selected to act as the trial judge from a total pool of seven active judges.

Given the broad authority of federal trial judges and her obvious pro-Trump bias, Cannon will be uniquely positioned to help the ex-President as the case unfolds. She will rule on all pretrial motions, including any motions to suppress the documents on Fourth Amendment grounds, as well as any that seek to dismiss the indictment for selective prosecution or prosecutorial misconduct. She will also have the last word on the admissibility of evidence at trial.

Cannon’s greatest impact, however, may be on jury selection. Under the federal rules of criminal procedure, the prosecution will only have six peremptory jury challenges, allowing it to automatically exclude potential jurors it believes will be unfair. After that, the prosecution will be limited to challenges for cause (such as implied or actual bias), which Cannon will have the sole power to grant or deny. It will only take one rogue juror who holds out for acquittal regardless of the evidence to spare Trump.

Even if Cannon were not biased herself, there is good reason to doubt her ability to supervise the high-profile selection of Trump’s jury. In a recent criminal case, according to a transcript obtained by Reuters, she arguably committed an egregious Sixth Amendment error when she excluded the family of a criminal defendant and the general public from her courtroom during jury selection, pointing to a lack of space. She also neglected to swear in the jury pool, and was forced to restart jury selection after realizing her mistake.

Cannon could also play a decisive role post-trial if Trump’s attorneys ask her to issue a directed verdict that would take the question of guilt out of the jury’s hands. Such motions are routinely made in criminal trials, but are rarely granted.

If all this seems like a prescription for disaster, take heart: Trump will soon be in the dock in the District of Columbia, Georgia, and New York State—all far beyond Judge Cannon’s reach.