Prior to filing an indictment against Donald Trump last year for allegedly mishandling secret documents, federal prosecutors had to decide whether to file the charges in Florida or Washington, DC. In the end, the choice to prosecute the former president in Florida has had a big impact and brought attention to how different the legal systems are in these two states. This difference was brought to light this week when the views of two federal courts in Washington, DC, were made public. This showed how much faster and more severely the case could have proceeded if it had stayed in Washington, DC.

The federal judge currently overseeing Trump’s case in Florida has a very different legal philosophy from the judges in the District of Columbia. The views of Chief Judge James “Jeb” Boasberg of the DC District Court and Judge Beryl Howell, his predecessor, made this clear. The arguments made by Trump and his co-defendants regarding attorney-client privilege and grand jury secrecy were met with strong skepticism by these judges; Judge Aileen Cannon in Florida has been considering these matters for months. This doubt implies that, had the case remained in Washington, DC, it could have moved forward faster and with more legal heft against Trump.

Over the recent holiday weekend, the federal judge supervising Trump’s case in Florida, Judge Aileen Cannon, found herself at the heart of a new argument surrounding a prospective gag order for the former president. This is an issue that judges in DC have already addressed. Judges Boasberg and Howell took a strong stand on cases that have resulted in major delays in Florida, as stated in their unsealed opinions. They were impatient with Trump and his allies’ defenses, especially when it came to attempts to conceal information under the attorney-client privilege and to maintain the privacy of grand jury proceedings.

 

Judge Cannon’s Delays Cast Doubt on Pre-Election Trial for Trump

The investigation against Trump for mishandling sensitive data is still pending, even though Special Counsel Jack Smith filed the indictment almost a year ago. Judge Cannon’s unwillingness to rule quickly on the matters at hand is mostly to blame for this delay. The likelihood that the case will get to trial before the election in November so seems dwindling. Prosecutors have requested again that Cannon respond to Trump’s right to make public comments about law enforcement and witnesses connected to the documents investigation. The reason for this request is that during the investigation of his Mar-a-Lago home in 2022, Trump has falsely claimed on multiple occasions that the FBI was ready to use lethal force against him.

An order to gag has already been imposed on Trump by federal judge Tanya Chutkan of Washington, DC, in a different criminal case pertaining to the 2020 election. He is prohibited by this order from speaking in a way that would intimidate witnesses or cause disruptions to the proceedings when he speaks about them. As for the prosecutors’ urgent pleas to restrict Trump’s public remarks in the papers case, Cannon has not yet replied.

A federal grand jury in Washington, DC, was tasked with gathering the majority of the evidence against Trump in the papers case. The grand jury convened several months after the FBI removed hundreds of secret documents from Trump’s Mar-a-Lago estate in August 2022. But in the last few weeks before prosecuting Trump in a federal court in South Florida, the Justice Department transferred the case to a grand jury in Miami. This change happened as a result of the fact that the majority of Trump’s purportedly illegal acts happened at Mar-a-Lago in Palm Beach, Florida.

There have been few public announcements about the choice to transfer the case to Florida, but this decision has been divisive in court disputes with the defense teams on confidentiality concerns. Special Counsel’s Office prosecutor David Harbach said, “The investigation that was ongoing before the DC grand jury had an adequate nexus to continue in Washington,” during a recent hearing before Judge Cannon. I’m not in a position to discuss the specific day that the decision to charge in Florida was taken or the internal discussions around that decision.

The lawyers for Trump and his co-defendants have been trying for months to take advantage of this shift to Florida in the hopes that Judge Cannon will be more sympathetic to the prosecution’s position than Judges Howell and Boasberg were. As part of this tactic, the prosecution has attempted to persuade Cannon to reevaluate key points of the case that Howell and Boasberg had previously decided, such as the prosecution’s ability to get testimony from Trump’s former lawyer, Evan Corcoran. The goal of Trump’s legal team is to have Corcoran’s testimony removed from the case—a move that would have been more difficult had the legal matter stayed in Washington, DC.

As per the finding that his communications with Trump were not covered by attorney-client privilege because they were being used to facilitate a criminal conspiracy, Judge Howell last year ordered Corcoran to testify before the grand jury. Corcoran gave in-depth allegations of Trump’s purported attempts to hide sensitive data from federal officials, which greatly aided in the indictment against the president.

  

Legal Expert Criticizes Judge Cannon’s Delay in Addressing Key Privilege Issues

The national security expert Bradley Moss, a Washington, DC, attorney, pointed out that Judge Cannon will have a “clear road map” to follow when addressing the attorney-client privilege problems as a result of Howell’s decision. Though the parties started arguing about this point in court documents back in February, Cannon has not yet scheduled a hearing on the matter. Moss expressed disapproval of the delay, saying, “It is inexcusable that she is still sitting on the matter.”

Cannon has demonstrated a stronger hesitation to make decisions on matters before her than the DC judges have. She has frequently permitted protracted rounds of arguments on the claims of the defendants and has given credence to attempts to veer the case away from its main concerns and toward arguments that are considered fringe by many legal experts.

Given the “strong evidence” that Trump “intended” to conceal sensitive documents, Judge Howell granted investigators access to the specifics of Trump’s talks with his counsel in a pre-indictment judgment. Her 84-page March ruling supported the prosecution’s allegations that Trump engaged in potentially illegal obstructive behavior; these allegations are now a central component of the criminal case. Howell’s investigation, which focused on a lot of the same behavior as the allegations against Trump, came to the conclusion that the prosecution had provided “sufficient” evidence of a crime to violate the attorney-client privilege. Although this standard is less stringent than what a jury would ultimately have to decide, it nonetheless forced Howell to take on some of the same defenses that Trump’s attorneys are currently putting up to Cannon.

For example, Howell refuted Trump’s claim that, in his capacity as a former president, he was entitled to keep secret documents, highlighting his legal need to “safeguard” such data. The “classified documents were stored in unauthorized and unsecured locations,” according to Howell. Cannon’s proceedings have been considerably complicated by this argument. Ultimately, the court denied Trump’s move to dismiss the lawsuit on the basis of this claim, but only after lengthy oral and written debates and a decision that omitted any discussion of the case’s merits.

Judge Boasberg, on the other hand, recently turned down a request made by Trump and his co-defendants to move some private grand jury records from Washington, DC, to Florida. Walt Nauta, Trump’s valet and co-defendant, initiated this request in order to examine a 2022 exchange between his lawyer and prosecutors following his decision to cease participating with the investigation. A warning regarding the possible harm to grand jury confidentially in the event that records were transferred to a different court that was not familiar with the grand jury’s past was added in Boasberg’s opinion. According to his ruling, Nauta’s counsel was attempting to use the request as a “fishing expedition” to try and manipulate the system in order to obtain anything that would help their case by going through the records.

Obama appointee Judge Boasberg cited a plethora of case law and earlier DC judgments, and he sent Cannon a “recommendation” for how to handle the secrecy of other grand jury papers that were more relevant to the case. His decision brought to light Nauta’s attorneys’ attempt to manipulate the system by looking for potentially helpful court records, which he found to be speculative and unfounded.

 

Florida Court’s Inexperience with Sensitive Data Complicates Trump Proceedings

Compared to the DC judges, Judge Cannon, a Trump appointment confirmed in late 2020, has far less expertise managing cases involving substantial political and national security interests. For example, Boasberg was formerly the head judge of the Foreign Intelligence Surveillance Court, which handles a lot of secret and national security cases. One of the nation’s most knowledgeable judges on attorney-client privilege disputes in politically sensitive investigations is Judge Howell, another Obama appointee. In contrast, Cannon works in a courthouse that just recently got a protected facility for analyzing sensitive data, and she has only presided over four criminal trials since her appointment.

Major disagreements over the national security materials that the defense may want to use in court have not yet been scheduled for hearings, and Cannon has been dragging out her handling of the classified records concerns in Trump’s case. Bradley Moss made a comparison between the DC judges’ efficiency and Cannon’s, pointing out the latter’s lack of exposure to the litigation process and the former’s prompt and thorough handling of these cases. This comparison highlights the difficulties and hold-ups that have plagued the Florida processes that fall within Cannon’s purview.