Trump prosecution could stretch well beyond 2024 election 

The Justice Department’s massive and complex legal case against Donald Trump is likely to dog the former president well into the 2024 presidential contest. 

The thorny issues raised in the classified documents battle, combined with Trump’s penchant for aggressively challenging suits, suggests a long-term fight that may not even end before Election Day next year.

And helming the case will be Judge Aileen Cannon, a Trump appointee who slowed the initial investigation with numerous rulings favorable to the former president. 

“It’s going to be very difficult to bring a case like this to trial within the year, given the highly sensitive classified information at issue,” Brian Greer, a former CIA attorney, told The Hill.  

“Plus, Trump is going to seek every delay possible. If Judge Cannon goes along with these delaying tactics, we’ll be looking at a trial in 2025 at the earliest.”  

The indictment, based on Trump’s handling of 31 documents classified among the highest levels, signals special counsel Jack Smith and the Justice Department (DOJ) plan to aggressively pursue the case. That approach, however, requires sorting out how to address the classified material both during discovery and in presentation to the jury. 

The high-level breakdown of the records in question suggest the Justice Department did not settle on “Goldilocks documents — documents that are sensitive but not too sensitive” and therefore more easily addressed at trial, said Brandon Van Grack, a former top national security lawyer at the DOJ.  

“These appear to be even more sensitive than your typical retention case, and what I would think from that is that the intelligence community very much is also focused on the fact that they view the conduct here as something that was potentially harmful and damaging to national security. So they’re taking it just as seriously as the Department of Justice is taking it,” he told The Hill.  

Just security clearances for Trump’s attorneys alone will take time, and even an expedited process could take several weeks. Cannon ordered Trump’s attorneys to begin the process no later than Tuesday. 

The discovery process — where the parties exchange the evidence they will present at trial — will also present opportunities for Trump challenges. 

Prosecutions resting on classified documents use a different process for discovery, all dictated under the Classified Information Procedures Act (CIPA), which lays out narrower grounds for what must be shared with the defense. 

“Instead of just being relevant, it needs to be relevant and helpful to the defense,” Greer said. 

The process allows for the government to redact and summarize some of the information and will also include a determination over how much of the evidence Trump and his attorneys can challenge.  

Justice Department lawyers Friday filed a motion for a protective order that would allow Trump to see the documents — but only in the presence of his attorneys. 

One of the bigger pretrial battles could come during a stage of requirements detailed under CIPA Section 5 that requires defendants to notify the government of any classified information they plan to use at trial.  

“Trump’s team will likely argue that the CIPA Section 5 notice requirement is unconstitutional, because it requires them to give some sort of notice of their defense to the government. That argument has been resoundingly rejected by the courts, but it will still be made by the Trump team,” Greer predicted. 

The DOJ can also push back on whether Trump’s team has been sufficiently specific about the evidence it plans to use at trial — in part because they may wish to further redact the evidence. 

Another likely battle is whether the DOJ can use the silent witness rule — a method of having experts testify in broad strokes about the classified records so that they can avoid declassifying them or making them public.  

Trump’s team is likely to push to declassify the evidence in the hopes the Justice Department will drop some of its charges. 

“They will want to put pressure on the government to have to declassify as much information as possible for trial,” Greer said. “If Trump’s lawyers get the court to rule that any document that he is charged with has to be declassified in order to be used at trial, it might cause the Department of Justice to rethink some charges.”  

Greer said in “99.9 percent” of similar cases, the Justice Department would seek a judge’s blessing to use the silent witness rule to avoid such issues. 

“It’s just a question of: Do you do something different than normal because it’s the former president? And because it’s President Trump, who’s going to have some sympathetic judges in the judiciary, especially Judge Cannon? That may cause the government to rethink some strategies,” he said. 

Van Grack said while the process will slow the case, the DOJ has likely already thought through many of these issues and will be prepared to quickly file on the matters. 

“Ultimately, the former president will be able to make those challenges,” he said. 

“There are delays anytime you’re talking about classified information, if nothing else, because there’s literally this additional process and litigation. But depending on the facts, it doesn’t have to be. I have done CIPA litigation on retention cases that have not materially delayed proceedings,” Van Grack added. 

Cannon will oversee all of the back-and-forth between the parties — another factor in determining the speed at which the case progresses. 

In Trump’s earlier challenge to the investigation, Cannon repeatedly sided with the former president, at one point agreeing with a Trump request to block the Justice Department from using the classified records it seized while also appointing a special master to review his privilege claims. 

Both were later overturned by the 11th Circuit Court of Appeals, but that was roughly four months after Trump began his initial suit. 

Some legal observers have suggested the Justice Department seek to remove Cannon to the case, a path they may be hesitant to pursue given the likely howls from critics. 

The Justice Department can still appeal any of Cannon’s decisions on an expedited basis, but even matters given priority before the court take time.   

Once the case actually does get to trial, the DOJ has suggested it could try the case itself in as little as 21 days. 

The stakes are high for Trump, who could face anywhere from 12 to 22 years in prison, based on an analysis of sentencing guidelines published in Just Security.   

Trump has vowed to fight the charges and has repeatedly maintained he did nothing wrong. 

“​​Indictment must be immediately withdrawn by the Injustice Department, with apology!” Trump wrote on social media Friday.  

Still, even if Trump is convicted by a Florida jury, it’s unlikely he’d be quickly placed behind bars.  

“Simply because of how criminal prosecutions work, and then how long they can take, how long we should expect a prosecution of someone who is as prominent and well-resourced and politically significant as Trump to take both prior to any trial and after, I find the odds that he might be in any sort of prison by November 2024 extremely low,” said Ankush Khardori, a former DOJ trial attorney specializing in major financial fraud. 

“Because he can stay out — even if he’s convicted at a trial — he can stay out pending appeals.”