Legal expert: Trump may be “overplaying his hand” — and it may get Judge Cannon "taken off the case"

Former President Donald Trump's attorneys are set to appear in court before Trump-appointed Judge Aileen Cannon in the Mar-a-Lago documents case on Tuesday, putting her in the spotlight after a series of pro-Trump rulings that were wiped out by an appeals court earlier in the investigation.

Cannon, who blocked the Justice Department from reviewing classified documents seized in last year's FBI search of Mar-a-Lago before her ruling was overturned, will preside over a pretrial conference to discuss the procedures for handling classified information in the case. The arguments come as Trump pushes to delay the trial indefinitely, citing his presidential campaign, which the special counsel Jack Smith's strongly pushed back on last week.

Cannon is expected to face additional scrutiny after her earlier rulings drew criticism from legal experts that she was overly favoring the former president.

"She is not going to want to do anything but go by the book. The challenge is there has never been a book like this," former U.S. Attorney Kendall Coffey, who served on the advisory committee that reviewed Cannon's judicial application, told the Associated Press. Whatever happens, he added, "the eyes of the world are on her. She is in the middle of writing a chapter in history."

Her ruling last September blocking parts of the documents probe and appointing a short-lived special master to review the materials was thrown out by the 11th Circuit Court of Appeals, which called her order a "radical reordering of our caselaw limiting the federal courts' involvement in criminal investigations."

Tuesday's conference is focused on the Classified Information Procedures Act, a law that governs how classified information is handled in criminal prosecution. It is intended to give a defendant access to key evidence while preventing potential leaks of classified information.

Trump's lawyers and prosecutors are also locked in a battle over the schedule of the trial. The DOJ requested a December trial start date before Trump asked to push it back indefinitely.

Dave Aronberg, the Florida state attorney for Palm Beach County, told CNN that Trump's attempt to delay the trial may have backfired.

"Jack Smith is now a pit bull, so he should have been careful what he asked for," he said. "But now he's saying the quiet part out loud. He's saying, 'don't even try me until after the election,' when he thinks he'll be president and then can order his Department of Justice to get rid of the whole thing."

Despite the pushback, Aronberg acknowledged that it would be "hard to try this case before the 2024 election" given the complicated matters surrounding the classified information.

The difference, he said, "is that Donald Trump is just saying, 'give me the whole enchilada, just postpone it indefinitely.' Whereas I think Judge Cannon is more likely to give him bits and pieces, delay here, delay there, and then you turn around, and it's already past the election. Essentially, it's death by a thousand paper cuts. But Trump may be overplaying his hand by asking Judge Cannon to go ahead and delay this thing indefinitely. I don't think he'll get that. If Judge Cannon grants that, I think she'll be reversed by the 11th Circuit and possibly even taken off the case."

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Some legal experts have downplayed the idea that Cannon could be taken off the case but former federal prosecutor Andrew Weissmann, who served on special counsel Bob Mueller's team, predicted that Smith may wait for her first "erroneous ruling" given "that she's had two decisions reversed in scathing opinions by a conservative 11th Circuit Court, including, by the way, judges appointed by Donald Trump."

"They could wait for her to make another misstep, appeal that and in that appeal ask it be reassigned to a different judge," he told MSNBC last month. "That's a route that, while it's not common, does occur. That would be the third time that she was reversed, not just in any case, but in this very investigation."

While Trump has repeatedly lashed out at judges overseeing his other legal matters, he heaped praise on Cannon on Sunday.

"I know it's a very highly respected judge. A very smart judge, and a very strong judge," Trump told Fox News, adding that he was "very proud to have appointed her."

"But she's very smart and very strong, and loves our country," he added. "We need judges that love our country so they do the right thing."