Gage Skidmore

Explain This

Gage Skidmore

Will We Ever See Donald Trump Behind Bars?

The former president's dance card is full of trial dates in federal and state courts across the country. Here's the over/under on what to expect.

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“I could stand in the middle of Fifth Avenue and shoot somebody, and I wouldn’t lose any voters, OK?” Donald Trump boasted at a campaign stop in Iowa back in 2016. “It’s, like, incredible.”

And for almost seven years, he was exactly right. 

From his first day in office when he flouted the federal anti-nepotism statute to install Jared and Ivanka in the White House, Trump waged a daily assault on democracy, busting through norms and laws like a malevolent Kool-Aid Man. He cashed in on his office, deployed the Justice Department as his own personal law firm, extorted a foreign government to harm his political opponent, and even incited a coup. And he still managed to get even more votes in 2020 than he did in 2016!

But now it looks like Trump’s luck may have run out. The former president is staring down criminal trials in Georgia, New York, Florida, and D.C. These may not cost him any votes among his loyal base, but they do have the potential to send him to prison for a long time. So it’s important to understand what is at stake in these four cases, even as every news cycle brings a deluge of stories about Trump’s legal woes.

In Georgia, Fulton County District Attorney Fani Willis charged Trump and 18 co-defendants with a conspiracy to interfere with the 2020 election and to submit a fraudulent electoral certificate to the National Archives. The allegations describe several interrelated plots, including Trump’s call urging Secretary of State Brad Raffensperger to “find 11,780 votes,” a pressure campaign on state legislators to reconvene and steal Biden’s 16 electoral votes, and the breach of voting machines in rural Coffee County.

This is the most complicated of the four indictments, and not just because of its wide cast of characters, including Rudy Giuliani, notorious Kraken lawyer Sidney Powell, and a motley crew of local weirdos. Georgia’s sweeping RICO law is far broader than the federal statute used to take down mobsters. It’s been used to prosecute everyone from street gangs to teachers who participated in a scheme to fraudulently inflate students’ standardized test scores. On top of this, the case is going to be highly dependent on the vagaries of Georgia civil procedure, something unfamiliar to your average cable news legal correspondent. 

Currently, two defendants have asserted their right to a speedy trial, for which jury selection will begin in three weeks. Five are seeking to remove their cases to federal court. One has taken a plea and agreed to cooperate with prosecutors. And presumably all the rest will seek to have their cases severed from the group because no one—not defendants, not lawyers, and certainly not jurors—wants to spend months in court sitting next to the patrons of the Star Wars bar

This case represents a major danger to Trump, particularly if and when additional co-defendants start cutting deals to avoid the ruinous expense of paying lawyers to appear in court for a trial where jury selection alone could take several months. But when that day of reckoning might come is very much an open question. 

In contrast, the election interference case brought in D.C. by Special Counsel Jack Smith is a precision-guided missile. Trump is the sole defendant, and he’s charged with obstruction and conspiracy to obstruct Congress by seeking to substitute his fake electors for Biden’s real ones. He’s also charged under a Reconstruction Era statute designed to protect the rights of all citizens to vote and have their votes counted—a fitting accusation for someone who sought to disenfranchise Black voters in major metropolitan areas and who falsely accused two Black poll workers in Atlanta of sneaking in suitcases of fraudulent ballots.

Trump’s primary goal with respect to the federal charges is to delay as long as possible in hopes that he’ll be back in the Oval Office in 2025 and able to pardon himself or simply order the Justice Department to drop the cases. Trump’s lawyers originally requested a D.C. trial date in 2026, but U.S. District Judge Tanya Chutkan scheduled the DC case for March of 2024. Since then, Trump’s lawyers have spammed the court with indignant motions accusing “the Biden Justice Department” of all manner of impropriety, while seeking to extract weeks of delay to respond to even the most mundane government filing. 

In the meantime their client spends much of the day, as he did during his presidency, screaming on social media and directing his followers’ rage toward his enemies. But now those enemies include prosecutors, potential witnesses, the jury pool, and even the judges presiding over his cases. Trump’s firehose of invective includes such chestnuts as “Deranged Jack Smith & his team of Thugs” and “WITCH HUNT!” as well as references to “a fraud dressed up as a judge in Washington, D.C. who is a radical Obama hack.” He has described Mike Pence, who will certainly be called to testify, as “delusional,” and called for the death penalty for General Mike Milley, the former chair of the Joint Chiefs of Staff. 

Judge Chutkan already faced a death threat from a Trump supporter who was arrested after leaving a voicemail calling the judge a “stupid slave n—–” and promising “If Trump doesn’t get elected in 2024, we are coming to kill you.” Prosecutors moved for a protective order, a.k.a. a gag order, to prevent the former president from intimidating witnesses, jurors, and the court. Trump’s counsel objected, loudly, and with the inevitable demand for more time to respond.

In contrast, Trump’s New York state prosecution has gone almost silent since he was indicted by a Manhattan grand jury in March for 34 counts of falsifying business records to hide the hush money payment to Stormy Daniels in 2016. Trump is alleged to have reimbursed his lawyer Michael Cohen for the $130,000 payoff to Daniels through a series of checks falsely denominated as payments for legal work.

Under New York law, this would normally be a misdemeanor, for which the two-year statute of limitations has long since lapsed. But if a false payment is undertaken to cover up another crime, it becomes a felony, for which charges are not yet time-barred. Here, Manhattan District Attorney Alvin Bragg hasn’t specified what the other crime is, instead making vague reference to violations of federal and state election law. To be fair, Bragg doesn’t have to specify the “other crime” at this stage of the case. But this yaddayaddayadda-ing over a crucial element of the charges has contributed to a broad consensus among legal commentators that this is the weakest of the four cases against Trump. 

After an initial appearance in April, the defendant isn’t due back in New York court until December. The trial was originally scheduled for late March 2024, but will likely be postponed to allow the federal cases to go forward first.

Finally, there’s the documents case in the Southern District of Florida, which should be a slam dunk. For 18 months after leaving office, Trump resisted government entreaties for him to simply return the records he’d pocketed on the way out of the White House, along with various “love notes” from dictators and commemorative knickknacks belonging to the American people. After the Special Counsel issued a grand jury subpoena for all documents bearing classified markings stored at his Mar-a-Lago home, Trump had his lawyers sign a declaration in June of 2022 attesting that a diligent search had been conducted and no further classified documents remained on the premises. But in August, FBI agents showed up with a warrant and discovered upwards of 100 additional classified documents at various locations on the property.

The resulting indictment depicts a cartoonishly inept scheme in which Trump and two of his valets, Walt Nauta and Carlos De Oliveira, conspired to hide government documents from Trump’s own lawyer Evan Corcoran. In the days before Corcoran was due to search the basement storage locker where the documents were being held, the valets furtively ferried boxes in and out, allowing Trump to remove government documents he wanted to keep for himself. The search was a sham, as was the affidavit attesting to it. And when the FBI subpoenaed security camera footage which would have shown Trump’s valets moving the boxes around to evade the search, the three tried unsuccessfully to delete the incriminating film.

In addition to video of Nauta and De Oliveira prowling around the property with flashlights and cameras, there is also a mountain of evidence the co-conspirators texted back and forth to each other, including that ridiculous photo of boxes of documents stacked in a Mar-a-Lago bathroom. There is also testimony from multiple witnesses, including Corcoran himself, since Judge Beryl Howell overruled his claim of attorney-client privilege under the crime-fraud exception. It would appear that the government has Trump dead to rights.

But …

… This case has been assigned to Judge Aileen Cannon, one of the youngest judges on the federal bench who was confirmed by the Senate after Trump had already lost the 2020 election. After the government search in 2022, Trump mounted a preposterous legal challenge to the validity of the warrant which authorized it. This would have been summarily tossed out of any courtroom in the land except for Judge Cannon’s. Instead, she permitted him to advance executive privilege claims as to classified documents, and even countermanded her own special master when he ordered Trump to specify which documents the FBI had “planted” on him, as he and his lawyers repeatedly alleged. In fact, Judge Cannon did everything she could to torpedo the prosecution of the man who appointed her to the bench and was only stopped by the Eleventh Circuit, which slapped her down in withering fashion.

Not surprisingly, Trump has never called Judge Cannon a hack, or a radical, or a “Democrat” plant on Truth Social. And while the judge has so far played this round conservatively, she seems at least receptive to Trump’s claims of impropriety in the grand jury process which may render some of the evidence against him inadmissible. Never mind that the grand jury was supervised by Judge Howell and Chief Judge James Boasberg, both of whom have been on the bench for decades.

In short, if the Florida prosecution goes sideways, it will likely be because of Judge Cannon. But all four of these cases represent a serious threat to Donald Trump’s continued liberty. And in all likelihood, at least the D.C. election interference case will go to trial before the 2024 election.

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