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Before federal prosecutors could indict Donald Trump last year on charges he mishandled classified documents, they had to decide whether to bring the charges in Washington, DC, or Florida.
They ultimately prosecuted the former president in Florida, a decision that proved fateful, as evidenced by the starkly different approach taken by the federal judge currently presiding over the criminal case in Florida and a judge in Washington, DC.
That approach was made clear last week when opinions from two federal judges in Washington were released that showed how swift and harsh the outcome for Trump could have been if the trial had remained in Washington.
And over the long weekend, the federal judge currently overseeing Trump’s case in Florida plunged into new arguments about gag orders against the former president, an issue already being addressed by a judge in Washington.
In recently released opinions, D.C. District Judge James “Jeb” Boasberg and his predecessor, Judge Beryl Howell, expressed deep skepticism of Trump and his co-defendants’ arguments about attorney-client privilege and grand jury secrecy that have been considered for months by Florida Judge Eileen Cannon.
Nearly a year after Special Counsel Jack Smith indicted President Trump on charges of mishandling classified documents, the case remains stalled due to Cannon’s unwillingness to rule on the issues at stake, making a trial unlikely before the November election.
Cannon is now being asked to comply with new requests from prosecutors to limit his ability to comment on law enforcement or witnesses involved in the documents case, especially since Trump continues to misleadingly suggest that the FBI was prepared to use deadly force against him during the 2022 raid on his Mar-a-Lago.
Tanya Chutkan, a federal judge in Washington who is overseeing a separate criminal case against the former president related to the 2020 election, issued a gag order to Trump several months ago barring him from commenting in a way that could intimidate witnesses or others in that case or prejudice the proceedings.
Cannon has yet to respond to prosecutors’ requests in a filing Friday night to restrict Trump’s speech.
Most of the evidence against Trump in the documents case was gathered through a federal grand jury in Washington, D.C., which continued to hear testimony months after the FBI seized hundreds of classified documents from Trump’s Mar-a-Lago estate in August 2022. But the Justice Department transferred the investigation to a Miami grand jury in the final weeks before indicting Trump in federal court in South Florida because much of Trump’s alleged criminal conduct took place at Mar-a-Lago in Palm Beach, Florida.
Prosecutors have made little public about their choice to move the case to Florida, but it has been a contentious topic, particularly in recent hearings before Cannon, amid a battle with the defense over confidentiality. “I would say that the investigation that was ongoing before the Washington grand jury was sufficiently relevant to continue in Washington. I’m not prepared to comment on the date that the decision was made to indict in Florida or what internal deliberations were taking place on that matter,” David Harbach, a prosecutor with the special counsel’s office, told Cannon at a hearing last week.
Defense lawyers for Trump and his co-defendants have spent months trying to capitalize on the move, hoping that Cannon thinks differently than Howell and Boasberg and might want to scrutinize prosecutorial choices.
Cannon is now being asked to reconsider fundamental parts of the case that Howell and Boasberg have already decided, including whether the prosecution can secure the testimony of Trump’s former lawyer, Evan Corcoran, before a Washington grand jury. Trump’s team is trying to exclude prosecution testimony altogether, an approach that might have made it harder for the defense if the case had stayed in Washington.
From the United States District Court for the Southern District of Florida
U.S. District Judge Eileen M. Cannon;
Last year, Judge Howell ruled that Corcoran’s conversations with Trump were not protected by attorney-client privilege because they were in furtherance of a crime, and ordered Corcoran to testify before a grand jury. Corcoran’s testimony ultimately influenced key parts of the indictment against Trump, including detailed descriptions of Trump’s alleged efforts to conceal classified materials from federal authorities.
Bradley Moss, a Washington-based lawyer with extensive experience in national security matters, said Howell’s ruling gave Cannon a “clear road map” for considering attorney-client privilege issues.
But Cannon has not even scheduled a hearing on the matter, which the parties began battling in court documents in February.
“It is inexcusable that she continues to let this issue go unaddressed,” Moss said.
Compared to his Washington counterparts, Judge Cannon has been reluctant to rule on issues put before him, often giving defenses broad latitude to argue their arguments multiple times in court, and has been open to attempts to drag cases away from their central issues and into arguments that a wide range of legal scholars consider heretical.
In a pretrial hearing that allowed investigators to obtain details of conversations between Trump and his lawyers that were otherwise protected by privilege, Howell said there was “strong evidence” that Trump “intended to conceal” classified documents. Howell’s 84-page opinion, issued last March, supported prosecutors’ arguments about potential criminal obstructionism by Trump that are now at the center of the criminal case.
Judge Howell analyzed many of Trump’s conduct in the indictment that was filed about three months later and determined that prosecutors had presented enough evidence of a crime to justify a privilege violation — a lower bar than a jury would ultimately have to meet in the case.
Alex Wong/Getty Images/File
Judge Beryl A. Howell
But the exercise required Howell to confront the very same defense of Trump that Cannon’s legal team is now presenting.
For example, Howell noted that even if Trump had the authority to store classified materials as a former president, the relevant law required him to “protect” the information, and in this case “classified documents were stored in unauthorized and unsecured locations.”
Similar arguments made by Trump in lower courts have stumped Cannon. She ultimately denied a motion to dismiss the case on the grounds that Trump could continue the lawsuit after leaving office, but only after hours of oral argument, additional written argument and a ruling that sidestepped the legal basis of the arguments.
Meanwhile, Judge Boasberg’s newly unsealed ruling rejected a request this month by Trump and his co-defendants to force a Washington judge to turn over several records of secret grand jury proceedings to Cannon.
The effort to transfer the records is being spearheaded by Trump aide and co-defendant Walt Nauta, who is seeking to review communications his lawyers had with prosecutors in 2022 after Nauta stopped cooperating with Trump.
Judge Boasberg’s decision included a warning (perhaps an implicit jab at Judge Cannon) that grand jury confidentiality could be compromised if the grand jury records were turned over to another court that was not fully familiar with the grand jury’s history.
It was clearly an impasse for the Washington, D.C.-based judge.
“Such a court may go beyond its area of expertise and disclose more material than necessary,” Boasberg wrote.
Judge Boasberg, an Obama appointee, cited extensive case law and even past rulings in Washington. He also sent “recommendations” to Judge Cannon on how to handle the confidentiality of other grand jury records that his court provided to the Florida court that are more relevant to this case.
Valerie Plesch/Bloomberg/Getty Images/File
Judge James Boasberg
Judge Boasberg’s ruling accused Nauta’s lawyers of exploiting Cannon’s system in Florida by trying to find secret past court records that they thought would be favorable to the defendant.
Boasberg pointedly called it a “fishing survey.”
“His requests extend to matters about which he knows nothing,” Boasberg wrote. “He believes that if he is transferred to Florida, the court presiding over his criminal case will scrutinize each and every record and extract any material that it believes is relevant to his defense.”
Still, Nauta’s lawyers continued to argue to Cannon last week that even without the old D.C. records, Boasberg can reopen the dispute previously handled by her court.
Judge Cannon, whose appointment was confirmed by President Trump in late 2020, has far less experience than his Washington counterpart, who handles cases where significant political ramifications intersect with national security interests.
For example, Mr. Boasberg previously served as chief judge of the Foreign Intelligence Surveillance Court, another powerful judicial body that works almost exclusively on national security issues. The Washington-based court reviews surveillance warrants related to national security intelligence issues and handles a wide range of classified matters.
Judge Howell, also appointed by President Obama, is one of the judges with the most experience in the nation with attorney-client privilege disputes that have arisen during President Trump’s jury investigation and has received more public attention on the issue in the politically sensitive investigation than any other judge in the country.
Cannon, meanwhile, has presided over just four criminal trials since President Trump appointed him to the bench in 2020, and in a courthouse so deserted that it didn’t have secure equipment to review classified records until months after his case was placed on his docket last June. He’s taken months to address the classified records issue in the case and hasn’t even scheduled hearings on a series of key disputes over national security records that the defense might want to use at trial.
“Just that increased exposure to this proceeding speaks to the speed and detail with which these two D.C. judges have handled these matters compared to Judge Cannon,” Moss said.
CNN’s Hannah Rabinowitz contributed to this report.
