According to some in his inner circle, Donald Trump’s most effective and not-so-secret weapon in his 2024 effort to reclaim the White House is a federal judge he appointed in Florida.
Judge Aileen Cannon is presiding over one of Trump’s two federal criminal cases — the classified documents case in the Southern District of Florida. In August 2022, the FBI raided Trump’s Florida club and estate, Mar-a-Lago, following his sustained refusal to return to the government a trove of classified documents he was hoarding at the club. This bizarre scandal led to a criminal case brought by Special Counsel Jack Smith.
Since last year, Trump’s attorneys have inundated the court with a range of motions and efforts to delay the trial. Instead of handling those matters quickly, Cannon has let motions languish for weeks without decision while holding what some experts see as unnecessary hearings to debate other issues, pushing a trial date further.
Cannon went even further last week with a ruling that tossed the May 20 trial date, postponing it indefinitely in order to first deal with what she said were “myriad and interconnected pre-trial and [classified information evidentiary] issues remaining and forthcoming.”
“My favorite member of the Trump campaign,” one Republican close to the former president — at least somewhat jokingly — tells Rolling Stone. A Trump adviser similarly says of Cannon: “She’s a godsend.”
According to two other sources with knowledge of the situation, Cannon’s delays and legal reasoning have become something of a running joke among the upper crust of Trumpworld, with various political advisers and campaign staff, lawyers, and media figures in the ex-president’s orbit remarking on how obviously and helpfully Cannon has been in the tank for Trump.
Late last year, many longtime associates of the former president, including some of his most senior campaign aides, had assessed that either or both of Trump’s federal cases — the classified documents case, or the election-subversion one — would likely inflict heavy damage on his 2024 poll numbers if either trial occurred before Election Day.
But thanks to the conservative U.S. Supreme Court, it now seems like a near-impossibility that Trump’s federal election subversion trial will start any time this year. The court’s decision to hear Trump’s immunity claims, pausing the election subversion case, so thoroughly delighted the Trumpland elite that some were “literally popping champagne” in response to the news. And thanks to Cannon’s repeated delays and decisions in Florida, there is virtually no chance that Trump’s classified-docs criminal trial will happen this year, either.
If Trump defeats President Joe Biden in November, it is all but certain that the new Justice Department would shut down Special Counsel Smith’s cases, eliminating the possibilities of federal prison sentences for Trump.
Looking beyond this year’s presidential election, Cannon — with her conservative credentials, openness to some of Trump’s more outlandish legal theories, and her willingness to make consequential procedural decisions that appear to benefit the political fortunes of the man who appointed her — could easily be a glimpse into the future of the federal judiciary, if Trump reconquers the White House and gets the chance to appoint even more MAGA-friendly judges.
Since last summer, according to two people with direct knowledge of the matter, the former president and presumptive 2024 Republican nominee has been consistently delighted by Cannon’s orders and decisions in the classified documents case, suggesting to close advisers that unlike other judges overseeing his different cases, Cannon is on their side.
Trump has also privately remarked in the past several months that if (or, in his insistence, when) he returns to the Oval Office, Cannon is a model for potential federal judicial picks because — in Trump’s own words — “we need more like her,” one of the sources recalls.
Brian Greer, a former attorney in the CIA’s Office of General Counsel, is one of few attorneys with firsthand experience with the Classified Information Procedures Act (CIPA), the federal law governing the use of classified materials in criminal trials which has occupied much of the court’s time as Trump awaits trial.
He says that Cannon has operated at an unusually glacial pace in dealing with the Trump defense team’s barrage of motions and attempts to delay the trial.
“This case was indicted in June. We’re now in May, and in terms of the scope of discovery, there’s been no material development in this case — just delay after delay. That, to me, is just inexcusable,” Greer says.
“CIPA cases can take a long time, but usually that’s because it takes a long time for the government to produce the classified material to the defense. They have to collect the classified records, get permission from the relevant agencies, and decide what to redact — and they’re usually aggressive in redacting,” according to Greer.
In court papers filed last month responding to Trump’s attempts to push a trial date back further, special counsel prosecutor Jay Bratt revealed that over 90 percent of the classified discovery materials have been available to the former president’s defense team since November.
“Here, the Justice Department produced most of the classified records right away, and with minimal redactions,” says Greer. “But instead of making the case move faster because of that, the judge just dragged her feet even more.
Prosecutors in the special counsel’s office have repeatedly accused Trump’s attorneys of engaging in a “pattern” of attempting to push the trial date back and filing “motions for the purpose of delaying trial.” At times, the special counsel’s frustration has spilled over when Judge Cannon has indulged the tactics.
In early April, Cannon ordered both prosecutors and Trump’s attorneys to submit competing jury instructions with their differing interpretations of the Presidential Records Act, which Trump has claimed allowed him to retain classified documents even after leaving office.
Annoyed at the order and sensing another opportunity for delay, Special Counsel Smith demanded that Cannon rule promptly on the issue herself. “It is purely a question of law that must be decided promptly. If the court were to defer a decision on that fundamental legal question it would inject substantial delay into the trial,” he wrote.
More than a month later, Cannon has yet to make a ruling on the subject.
