Even before her bombshell decision on Monday to dismiss former President Donald Trump’s classified documents case, Judge Aileen Cannon had made any number of unorthodox rulings.
In fact, since Cannon took control of the case in June 2023, many of her decisions have been so outside the norm that they have fueled intense criticism of her legal acumen, stoked questions about favoritism toward Trump and slowed the documents case sufficiently that it would not come to trial before Election Day.
Still, almost no one, including some defense lawyers working on the case, expected Cannon to throw out the charges against Trump by ruling that Jack Smith, the special counsel who filed the indictment, had been unconstitutionally appointed to his job — especially on the first day of the Republican National Convention.
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The ruling upended 25 years of Justice Department procedure for naming and governing special counsels and called into question decisions by previous courts reaching back to the Watergate era.
“The very definition of an activist judge, she has single-handedly upended three decades of established law historically used fairly and in a bipartisan manner,” said Joëlle Anne Moreno, a law professor at Florida International University.
From the moment that Cannon was assigned to the case, there were questions about her ability to handle it. She took control of one of the most significant prosecutions in American history, rife with legal and political complexities, even though she had been a judge for less than four years and had extremely limited experience in overseeing criminal trials.
On top of all that, the main defendant was the president who had nominated her to the federal bench.
Her colleagues in the Southern District of Florida were concerned enough about her stewardship of the case that not just one, but two of them approached her early in her tenure and asked her to consider stepping back and handing off the matter to another federal judge.
One of the jurists — the chief judge of the district — suggested it would be inappropriate for Cannon to continue on the case because of a ruling she had made in Trump’s favor in a related civil case after the FBI had searched Mar-a-Lago, the former president’s private club and residence in Florida, in August 2022.
In a move that drew national scrutiny and criticism, Cannon intervened in the civil case and barred the Justice Department from using any of the documents that agents seized from Mar-a-Lago in their inquiry until an independent arbiter had sorted through them for any that were privileged.
That decision was quickly reversed in a stinging ruling by the 11th U.S. Circuit Court of Appeals in Atlanta, which said she never had legal authority to get involved in the first place.
Over and over, throughout her handling of the documents case in U.S. District Court in Fort Pierce, Florida, Cannon has made similarly unusual decisions, often showing a willingness to grant a serious audience to some of the former president’s most far-fetched defense claims.
She has also repeatedly scheduled hearings in court to debate issues that many federal judges would have dealt with on the merits of written filings alone. And that has made it all but certain that the case will not reach a jury until well after the election in November — one of Trump’s overarching legal and political objectives.
Many legal experts questioned Cannon’s decision to hold a hearing last month on the issue of Smith’s appointment, arguing that several courts reaching back to the Watergate era had already upheld the legality of independent prosecutors.
The hearing was even odder, the experts pointed out, because the judge allowed outside parties who had filed friend-of-the-court briefs to address her directly for up to 30 minutes — a practice that rarely takes place at the trial level and is more common in appellate-level courts like the Supreme Court.
Entertaining direct arguments from these outside parties was a signal that she was taking Trump’s motion to dismiss on the appointments question seriously, Joel S. Johnson, an associate professor at Pepperdine Caruso School of Law, said last month before the hearing.
Cannon has her defenders. She approached the question of the constitutionality of the special counsel appointment with the thorough preparation of a circuit judge, said Josh Blackman, a law professor at South Texas College of Law Houston who argued against the legality of the special counsel before her at the hearing last month.
“I’ve rarely seen a district court judge this well prepared,” Blackman said. “She knew the cases, she knew the statutes and I suspect she had already written most of that opinion already.”
Paul Butler, a former federal prosecutor in the Justice Department’s public integrity section, said that even though Cannon’s ruling on Monday was unusual and rejected by other judges, it is also defensible in the context of recent Supreme Court decisions.
He cited the court’s decision granting Trump substantial immunity for actions he took in office and other decisions as “legal doctrine that upsets settled principles on separations of power and presidential accountability.” In a concurring opinion in the immunity decision, Justice Clarence Thomas had called for reexamining the legality of the appointment of special counsels.
But the hearing and decision on Smith’s appointment were hardly the only unusual moves by Cannon.
In one of the more striking aspects of her handling of the case, Cannon has ignored a common practice in the Southern District of Florida, where she sits, of trial judges passing off routine motions to the magistrate judge attached to a case.
Cannon has not delegated any motions to the magistrate judge in this case, Bruce E. Reinhart. And Reinhart knows the case well: He approved the search warrant used by the FBI two years ago when agents descended on Mar-a-Lago and hauled away a trove of classified material that is central to the case.
This spring, in another unusual move, Cannon ordered the defense and the prosecution to write dueling instructions for the jury that seemed to take for granted one of Trump’s most far-fetched defense claims: that he could not be tried for holding on to a trove of classified documents because he had designated the materials in question to be his own personal property under a law known as the Presidential Records Act.
By appearing to adopt the former president’s contentious position on the act, Cannon seemed to be nudging any eventual jurors toward acquitting Trump or even leaving open the possibility that she herself could acquit the former president near the end of the proceeding by declaring that the government had failed to prove its case.
“I have never seen a case where one would contemplate giving the jury alternative instructions: ‘Decide the case on this hypothetical scenario and then answer the question in an alternative understanding of the law,’” said Margaret Kwoka, a professor at Ohio State University’s Moritz College of Law.
Cannon has rarely issued rulings in the documents case that have been longer than 15 or 20 pages, and has often made decisions without revealing much about her legal reasoning.
But her order on Monday dismissing the case because of Smith’s appointment was 93 pages and full of a sweeping tour of historical events reaching back through the Watergate affair to the Teapot Dome scandal of the 1920s.
“It’s significant that this 90-plus-page decision is more erudite with more traditional citations than some of Judge Cannon’s other opinions,” said Butler, the former federal prosecutor.
Frustrations with Cannon have been mounting for months among members of Smith’s team, including one of his top deputies, David Harbach, who has twice lost his temper with the judge during hearings in her courtroom.
It is likely that prosecutors will appeal this ruling in particular to the 11th Circuit in Atlanta, which issued the rebuke against Cannon two years ago over her decision about a special master.
Alan Morrison, a professor at George Washington Law School, said the order to dismiss the case Monday may end up having a positive outcome for Smith.
“He can now take an appeal and when he prevails, he can ask the court to reassign the case to another judge,” Morrison said.
“Of course, it was clear a long time ago that she would never allow the case to be tried before Election Day — if ever,” Morrison added. “And so this order does nothing to impact the trial date adversely, in the real world.”
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