Trump judge’s thin criminal trial resume comes with a twist

Aileen Cannon, the federal judge overseeing Donald Trump’s latest criminal case, has run just four, relatively routine criminal trials in her short tenure on the bench — a stark contrast to the historic and complex proceedings she’s about to undertake related to the former president.

A review of the Southern District of Florida dockets show Cannon’s criminal work has consisted almost entirely of a few categories of cases: distribution of a controlled substance, illegal reentry of people who had previously been deported, felons in possession of firearms and child pornography or trafficking. Nearly all have resulted in plea agreements, and the four that did not were handled in brief trials that lasted no more than three days apiece in court.

Those cases have featured few significant opinions or rulings of note on complex issues of law. And Cannon, 42, has almost always sided with prosecutors on routine challenges to evidence, motions to suppress evidence by defendants and efforts to dismiss various cases.

Cannon’s thin resume, combined with her surprisingly deferential rulings to Trump — who appointed her in November 2020 — in a civil lawsuit challenging the FBI raid of his Mar-a-Lago estate last year, have raised questions about her readiness for the complexities of the first-ever federal prosecution of a former president. Prosecutors say he hoarded national military secrets at his Mar-a-Lago estate after leaving office and concealed them from government officials seeking to recover them.

There’s one exception, however, to Cannon’s judicial history that has largely escaped scrutiny. For nearly one-and-a-half years, she’s shepherded a complex, 10-defendant health care fraud case to the verge of trial, and in the course has litigated tangled and fraught issues of attorney-client privilege and motions to suppress — some of which could be precursors to battles in the upcoming Trump case.

The health care fraud indictment, which was filed in Feb. 2022 and generated bursts of media attention early on, is slated to go to trial on July 10, though one of the defendants is seeking to postpone the start until Sept. 25. Five of the defendants have pleaded guilty but the others appear intent on proceeding to trial.

Cannon has actively navigated the latest rounds of pretrial motions even as the Trump case landed in her court, including complicated decisions related to efforts by prosecutors to pierce attorney-client privilege, a near exact parallel to issues that have arisen in Trump’s long-running case.

“Such a release is warranted under the crime-fraud exception to the attorney-client privilege and work-product doctrine,” the government wrote in a recent filing.

If the case goes to trial this year, it’s likely to be the most significant criminal trial experience Cannon has had to date — and the protracted pretrial phase is a notable comparator for what may be to come in the Trump litigation.

Among her more recent rulings in the case: A decision in favor of federal prosecutors, rejecting a claim by the defendants that the government had failed to turn over exculpatory material. She has also sided with the government on a defendants’ demand for access to grand jury transcripts, on a defendant’s motion to suppress information seized from his email accounts and on defendants’ motion to dismiss charges.

Earlier this month, Cannon agreed with prosecutors’ demand for details from defendants about whether they would seek to defend themselves in trial by claiming their actions were based on the advice of attorneys — a common claim Trump makes in connection to allegations of potential crimes or controversial actions. In the same ruling, she swatted down a slew of defendants’ efforts to restrict the type of testimony the government intends to offer.

And Cannon is in the midst of weighing another complicated trial issue with parallels to Trump: Efforts by the Justice Department to share evidencewith prosecutors collected by a so-called “filter team”

Also of note in the proceedings: Cannon partially granted a motion by the Miami Herald to unseal key sealed documents in the case, agreeing to do so with redactions sought by the government.

Although Cannon’s criminal work as a judge has rarely led to trial, she has handled dozens of cases that have reached plea agreements. She’s issued no notable opinions in those cases, which have largely proceeded without controversy or significant legal disputes.

A review of dockets in her southern Florida district shows that the lengthiest sentence she has doled out was nearly 26 years to a man who pleaded guilty to trafficking minors. She has delivered similar sentences in a handful of other trafficking or child pornography cases.

Notably, Cannon has at times favored “consecutive” sentences, meaning the sentences for each charge are added up to make a longer sentence than if she opted to run them concurrently.

For example, in November 2022, Cannon handed down a 175 month sentence to a man who pleaded guilty to carjacking and firearms trafficking, combining a 91 month sentence on the first count and an 84 month sentence on the second count to result in the lengthier jail term.

One of Cannon’s four criminal trials was a two-day proceeding for a defendant charged with threatening and hurling a chair at a federal prosecutor after he was found guilty in a separate criminal case. After a jury found the man guilty, Cannon sentenced him to 80 months in prison — consecutive to the 210 month sentence he was already slated to serve for his conviction in the other case.

The most common cases Cannon has handled as a judge have been for “reentry of deported aliens,” relatively routine matters that have nearly all resulted in plea deals and sentences that ranged up to 1.5 years.

Before her confirmation to the district court bench, Cannon spent nearly eight years in the Justice Department, first as a Criminal Division attorney before moving to the appellate division, where she defended the Justice Department before the Eleventh Circuit Court of Appeals. She handled four trials as an assistant U.S. attorney as well, also relatively routine cases similar to those she has presided over as a judge.

“I prosecuted 41 defendants to conviction for a wide range of federal firearms, narcotics, fraud and immigration offenses,” Cannon wrote in her judicial questionnaire provided to the U.S. Senate. In two of them, she noted, she served as lead counsel. In two of them, she was associate counsel.

In one of Cannon’s four criminal trials as a prosecutor in 2014, the defendant, Davie Rodriguez, was detained pretrial by none other than Magistrate Judge Jonathan Goodman, who presided over Trump’s arraignment earlier this week.