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Is Bringing the Trump Documents Case in Florida a Mistake?



Former President Donald Trump’s best defense to the 38-count indictment brought against him by the Justice Department may turn out to be the decision by DOJ to have brought the case in Florida rather than Washington, D.C.

The case against Trump looks strong based on the indictment’s compelling detail of Trump’s alleged mishandling of national defense documents and efforts to obstruct justice. Evidence referenced in the charging documents include text messages from Trump’s co-defendant and personal valet, Walt Nauta, audio of Trump himself seemingly admitting he knew he could not de-classify documents once he left the Presidency, as well the notes of Trump’s own lawyer with all of it woven into a narrative that seeks to explain to the court and American public why the case is not about mere sloppy document management. Thus far the defenses put forth by Trump and his legal team fail to impress.

The legal defenses—I’m not counting Trump’s various insults directed at Special Counsel Jack Smith as legal defenses—thus far appear to fall into two buckets: prosecutorial misconduct and supposed de-classification of documents. The prosecutorial misconduct may be based upon reports that prosecutor Jay Bratt, Chief of the DOJ’s Counterintelligence section, may have engaged in conversation with Nauta’s defense lawyer, Stanley Woodward, that included bringing up Woodward’s application to become a judge.

The conversation took place during a meeting between prosecutors and Woodward in which the prosecutors sought to convince Woodward that Nauta should cooperate with DOJ against Trump. Woodward has filed a letter under seal with Judge Jeb Boasberg, Chief Judge of the federal district court in Washington, D.C., which claims that this conversation supposedly was meant to suggest that Woodward’s judicial application to become a judge in D.C. Superior Court could be given favorable consideration if Woodward’s client cooperated—in essence some type of bribe.

Starting with the fact that the DOJ’s Counterintelligence section has zero input into D.C. Superior court judgeships, this allegation is unlikely to go anywhere past Boasberg’s desk as it really relies upon the “deep-state” conspiracy notion that the entire Biden administration is allied against Trump and will do anything to tank his candidacy.

Similarly, Trump’s declassification argument has always been weak, whether it be based upon Trump claiming he can declassify merely by thinking about it to the fact that Trump’s own aides deny that Trump ever gave an order to automatically declassify any documents he took with him to the White House residence.


In any event, counts 1-31 of the indictment fall under the 18 U.S.C. section 793(e)—referred to as the “Espionage Act”—do not require that the documents at issue be classified at all but only that Trump willfully retained national defense information. In sum, the defense that Trump and his team have previewed so far look weak.

Ironically, the biggest help to Trump may end up being the DOJ’s decision to bring the documents case in Florida rather than Washington, D.C. Florida is better for Trump than D.C. because it’s a more conservative and Republican state with a jury pool potentially more sympathetic to Trump than would be D.C.’s presumably more liberal and Democratic jury pool—a jury pool that has thus far produced convictions of the Proud Boys and Oath Keepers for seditious conspiracy and some 78 convictions at trials for Jan 6 defendants.

But the biggest help to Trump likely would be the fact that Trump-appointed federal judge Aileen Cannon could preside over the case. Cannon was the judge who last year baselessly appointed a special master to review documents seized during the Mar-a-Lago search warrant that yielded critical evidence for Trump’s indictment. Cannon’s rulings were widely criticized and ultimately reversed by the 11th Circuit federal court of appeals. The choice of Florida is particularly surprising because up until recent reporting all the investigation and grand jury work appeared to be centered in D.C.

U.S. Special Counsel Jack Smith makes a statement to reporters about the 37 federal charges returned by a grand jury in an indictment of former U.S. President Donald Trump on charges of unauthorized retention of classified documents and conspiracy to obstruct justice at Smith’ offices in Washington, U.S. June 9, 2023.

REUTERS/Leah Millis

Judge Cannon was reportedly assigned to the case through an apparently unbiased random process. If this is true, then Cannon is unlikely to be shaken from the case even if the DOJ were to try to move to disqualify her. While a mechanism exists for this to happen in 28 U.S.C. section 455(a), which provides for disqualifications when a judge’s “impartiality might reasonably be questioned,” such a motion is hardly a slam dunk way to get rid of Cannon. Nor would the optics of such a motion be good for the DOJ since it would open them up to Trump claiming that prosecutors were “judge-shopping.”

So, why would the DOJ take the chance of bringing the case in a jurisdiction more favorable to Trump and risk drawing a judge who previously appeared to favor Trump with questionable legal rulings?


While we have no window into the internal deliberations that must have gone on in making this crucial strategic decision, one consideration the DOJ had to consider was the legal question of venue. As pointed out by Andrew Weissmann and Ryan Goodman in Just Security, a pending Supreme Court case raises the possibility that trying a case in the wrong venue might preclude the case from being re-tried in the correct one.

Such a possibility might have given the DOJ—particularly a DOJ led by a former federal court of appeals judge—some pause. Prosecutors may also have been worried that bringing the case in D.C. would lead to time-consuming pre-trial litigation about venue that would play into Trump’s usual delay tactics with every day of delay bringing the case closer to the red zone of the 2024 Presidential race.

Another potential factor that cannot be ignored is Attorney General Merrick Garland’s well-known goal of trying to rehabilitate the DOJ’s reputation after Bill Barr turned the department into a political weapon for Trump. Garland’s mission to protect the DOJ from accusations of partisanship may have led him to believe that bringing the case against Trump in Florida would prove the DOJ was not forum shopping for an anti-Trump venue. But Garland’s efforts to avoid criticisms of being partisan have thus far proven to be futile as Republicans attack the DOJ for being politically “weaponized” on a daily if not hourly basis.

It is not only the first federal indictment ever brought against a former President, but it accuses the former Commander-in-Chief of the country of endangering national defense and then trying to cover it up.

Whatever the reason was for bringing the case in Florida—and there may be very sound reasons for it that we are not privy to—the decision is fraught with risk. As a former prosecutor, I much prefer getting a conviction and having to defend it on appeal than facing delay and possible derailment of the case before it ever reaches trial. Judge Cannon poses precisely such a risk.

Special Counsel Jack Smith and his team have done an outstanding job of quickly investigating a factually complex case that is historically momentous for its gravity. It is not only the first federal indictment ever brought against a former President, but it accuses the former Commander-in-Chief of the country of endangering national defense and then trying to cover it up. But the search warrant that yielded the crux of this case was executed on August 8, 2022 and despite that search yielding more than 100 documents marked classified located in unsecure locations like Trump’s desk drawers and despite the months of requests to Trump, including a grand jury subpoena that were not complied with, AG Garland did not appoint Smith until November.

Moreover, the DOJ has presumably been investigating Trump’s role in the Jan 6 riot for more than two years and long before Smith was appointed. Such delay in resolution of potential criminal actions by Trump have done little either to rehabilitate the DOJ’s reputation or to protect our democracy from further partisan strife. As the saying goes: justice delayed is justice denied.


Source: The Daily Beast

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