Emerging Portrait of Judge in Trump Documents Case: Prepared, Prickly and Slow

Judge Aileen M. Cannon. (Southern District of Florida via The New York Times)
Judge Aileen M. Cannon. (Southern District of Florida via The New York Times)

A few months ago, a top prosecutor on former President Donald Trump’s classified documents case stood up in court and told Judge Aileen Cannon that he was concerned about the pace of the proceeding, gingerly expressing his desire to keep the matter “moving along.”

Almost instantly, Cannon got defensive.

“I can assure you that in the background there is a great deal of judicial work going on,” she snapped. “So while it may not appear on the surface that anything is happening, there is a ton of work being done.”

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In some sense, Cannon had a point. Much of what judges do unfolds out of sight in the sanctity of their chambers.

But at seven public hearings over more than 10 months, Cannon has left an increasingly detailed record of her decision-making skills and judicial temperament.

The portrait that has emerged is that of an industrious but inexperienced and often insecure judge whose reluctance to rule decisively even on minor matters has permitted one of the country’s most important criminal cases to become bogged down in a logjam of unresolved issues.

She rarely issues rulings that explain her thinking in a way that might reveal her legal influences or any guiding philosophy. And that has made the hearings, which have taken place in U.S. District Court in Fort Pierce, Florida, all the more important in assessing her management of the case.

Regardless of her motives, Cannon has effectively imperiled the future of a criminal prosecution that once seemed the most straightforward of the four Trump is facing.

She has largely accomplished this by granting a serious hearing to almost every issue — no matter how far-fetched — that Trump’s lawyers have raised, playing directly into the former president’s strategy of delaying the case from reaching trial.

It appears increasingly likely that the documents case will not go to a jury before Election Day, and that the only trial that Trump will face this year will be the one now ending in Manhattan, where jurors began deliberating Wednesday over whether he falsified business records in connection with hush money payments to a porn actor.

Still, the next few weeks will bring Cannon’s handling of the case in Florida into even sharper focus.

She may soon rule on a request by Jack Smith, the special counsel overseeing the two federal prosecutions of the former president, to ban Trump from making public statements that could endanger federal agents working on the documents case. That move, which the judge denied this week on procedural grounds, came in response to the former president’s baseless assertion that the FBI was authorized to use deadly force against him during the search two years ago of Mar-a-Lago, his private club and residence in Florida.

After a hearing in June, Cannon will also have to make a significant decision on whether to give Trump’s lawyers access to communications between Smith’s team and top national security officials. The lawyers made that request hoping to bolster their contention that the so-called deep state colluded with the Biden administration to bring the charges.

A former federal prosecutor, Cannon graduated from Duke University and the University of Michigan’s law school, where she joined the conservative Federalist Society.

She was nominated to the federal bench by Trump during his final months in office and was confirmed by the Senate just days after he was declared the loser of the 2020 election.

She was already under scrutiny when she got the classified documents case last June because of a decision she made well before the indictment was filed. That ruling, which shut down the investigation into Trump until an independent arbiter sorted through reams of materials seized from Mar-a-Lago, was so legally dubious that the appeals court sitting over her reversed it in unusually scathing terms.

Since then, Cannon has shown little of her human side in court, taking a businesslike approach to the proceedings, which always begin the same way.

Invariably entering her courtroom on time, she first admonishes those in the gallery not to use electronic devices and reminds them of her rule forbidding getting up while a hearing is in progress. She then lays out the issues at hand and recounts the documents she has received that will inform the conversation.

Even though she has been on the bench for only four years and has limited experience handling criminal cases, it is often clear that Cannon has done her homework.

In mid-March, for instance, she was discussing the key elements of the Espionage Act with Emil Bove, one of Trump’s lawyers and an expert on classified information cases. At one point, she pushed back at Bove’s contention that a section of the act requiring “national defense information” to be present in any documents charged in an indictment was so vaguely written that it was essentially unenforceable.

“There has been a fair amount of litigation, I think, on the defense information prong,” Cannon said. “So it would be hard to say, based on the current state of decisional authority, that that prong, in and of itself, is unconstitutionally vague.”

Even though it meant that he had lost the point, Bove had to agree.

“I can’t fight with the way that Your Honor phrased that,” he said.

That exchange, however, was a far cry from one that occurred last week when Cannon was debating with Jay Bratt, one of the prosecutors, about a common theory of legal liability called the Pinkerton rule. The rule holds that all members of a conspiracy can be held accountable for any crimes committed by their co-conspirators.

Bratt said the rule would likely apply to Trump’s dealings with his two co-defendants, Walt Nauta and Carlos De Oliveira, employees of Mar-a-Lago who have been accused of conspiring with the former president to obstruct the government’s repeated efforts to retrieve the classified materials.

Cannon seemed a bit perplexed and asked Bratt what authority he intended to rely on in applying the Pinkerton rule. Bratt seemed almost sheepish in having to lay things out for her so simply.

“So the authority is Pinkerton,” he said, and launched into a quick explanation.

One of Cannon’s most enduring habits is her tendency to ask the same question several times. It is never quite clear if she does not understand the answers she is receiving or is trying to push back against them.

At last week’s hearing, she did this to Stanley Woodward Jr., Nauta’s lawyer, as she considered his request to order prosecutors to provide him with internal communications that could help support his claims that the case against his client had been brought vindictively.

The communications Woodward was looking for concerned a meeting he attended at the Justice Department nearly two years ago where, he claims, Bratt threatened to derail a judgeship he had applied for if he did not prevail on Nauta to cooperate against Trump.

When Cannon asked Woodward what he actually wanted from the government, his answer seemed simple enough: any messages exchanged by prosecutors that mentioned his name. The judge then asked a second time, telling Woodward to give it to her “slowly.”

But even after that, it seemed that she was still a bit confused.

“All right,” she said, this time referring to notes she had taken. “So I understand your request. It’s, quote, ‘All documents, communications concerning Mr. Woodward.’ ”

Something similar happened moments later when Cannon turned to David Harbach, one of the prosecutors, to discuss Woodward’s request.

Harbach had just spent the better part of five minutes telling the judge that Woodward’s claims of misconduct were a “fantasy” and that, under the law, he was not entitled to rummage around in the government’s private messages.

But Cannon seemed to miss his point, asking Harbach if he was suggesting that prosecutors did not have any of the messages that Woodward wanted. No, he told her, explaining again that Woodward had failed to present any evidence that would even merit turning over what he wanted.

“So I guess what you are saying is you’re not sure?” she asked.

No, Harbach said for a third time, once more trying to explain that Woodward’s description of the meeting in August 2022 was entirely false and that the normal legal threshold for handing over private communications had simply not been reached.

“I know you disagree with the factual recitation of the August meeting,” Cannon said. “But would that provide a basis for the discovery request?”

Now clearly frustrated, Harbach said as plainly as he could that Woodward’s request had no basis in either fact or law.

“This is what I’m trying to tell you,” he all but shouted at the judge.

That discussion ultimately ended with Cannon telling Harbach he needed to “calm down.” It was emblematic of the dwindling reserves of patience between Cannon and the prosecutors.

In October, for example, Cannon lashed out at Harbach at a different hearing about whether Woodward had a conflict of interest in the case. The question revolved around the fact that Woodward was representing Nauta, one of the defendants, and had formerly represented a man likely to testify for the government at trial.

When Harbach expressed concern that Woodward might have to cross-examine a former client — a situation that could easily lead to a conflict — Cannon chided him for having failed to mention that possibility in his written filings submitted before the hearing.

Citing Harbach’s “last-minute introduction of an issue that was not briefed,” she abruptly ended the hearing and assailed the prosecution for “wasting the court’s time.”

But she acted very differently at the hearing last week when Woodward made several arguments about his claims of vindictive prosecution that had never appeared in any of his filings. Cannon hardly seemed to notice that he had wandered from his script, let alone rebuke him.

There is one subject the defense loves to talk about that always seems to set Cannon on edge: Trump’s presidential campaign. While she has allowed his lawyers leeway in using their briefings to make political arguments, she has repeatedly shut them down when they have tried to raise the subject of politics in court.

In early March, Bove began an argument on a highly technical legal issue by complaining that Trump should not have been in court at all that day, but instead should have been out campaigning.

Apparently annoyed, Cannon cut him off.

“OK, OK,” she said. “Can we talk about the actual legal issues?”

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