Should Trump go to jail? The 2024 election could become a referendum on that question

REUTERS/Lindsay DeDario

The 2024 election will determine whether Donald Trump returns to the White House. It could also determine if he will face time behind bars.

For Trump, who is now facing his third criminal indictment — this time for his attempts to overturn the 2020 election and obstruct the transfer of presidential power — winning means more than just ego, redemption, settling scores, or the country's future.

"This election could very well be about Donald Trump's personal freedom," said Ari Fleischer, a long-time Republican strategist. "It's not an exaggeration to say that if convicted, he could be sentenced to prison unless he wins and uses the justice system to reverse, stop, or drop the charges."

The deeply personal stakes for Trump add to what is already an unprecedented election in modern history. It's now not just a debate about the nation's challenges, but a partisan battle over whether the 77-year-old former president and GOP frontrunner should be incarcerated. Addressing this issue head-on, Trump ally Rep. Marjorie Taylor Greene, R-Ga., tweeted that she "will still vote for Trump even if he's in jail."

Critics have long asserted that Trump's fear of prosecution was a major motivator for his decision to launch another campaign. While Trump denies this, insisting that charges would not have been brought if he had chosen not to run, the new indictment intertwines his campaign and legal issues.

"The legal messaging is the political messaging, and the political messaging is the legal messaging," explained Trump campaign spokesman Steven Cheung. "It's part of our campaign strategy. Trump has placed significant emphasis on legal issues in his campaign, and from our perspective, it's effective messaging."

The combined total of 78 state and federal charges against Trump is already dominating his campaign speeches. He portrays himself as the victim of a politicized Justice Department aiming to harm President Joe Biden's chief political rival. At rallies, he tries to frame the charges as an attack not only on him but also on his supporters.

"They're not indicting me, they're indicting you," he told the crowd at a recent rally in Erie, Pennsylvania.

On a practical level, Trump is navigating an unparalleled challenge, campaigning while facing potential trials in at least three different jurisdictions.

He is set to appear in federal court in Washington on Thursday to address the latest charges before headlining an Alabama Republican Party event on Friday. He faces another arraignment in Florida next week, where additional criminal charges related to his handling of classified documents have been filed. This will be between campaign stops in New Hampshire and a potential trip to the Iowa State Fair.

Trump also faces the possibility of new charges in Atlanta linked to his efforts to overturn the 2020 election results in Georgia. He must also decide whether to participate in the first Republican presidential debate on August 23.

Trump campaign officials are not concerned about these logistical challenges.

"President Trump's campaign will not be impacted by the deep state's efforts at election interference no matter how hard they try," stated Trump senior campaign adviser Jason Miller. He argued that Trump and his team are experienced in dealing with such situations.
Cheung emphasized that no campaign events have been rescheduled or canceled due to legal proceedings, and if anything, more stops have been added.

"It's full speed ahead," he said before the latest indictment.

However, Trump's challenge extends beyond politics. Each of the cases against him — spanning from the Florida classified documents case to New York allegations of improper hush-money payments to women, and the recently released indictment — will require intense preparation.

"Under normal circumstances, it's impossible to prepare for more than one criminal trial at a time," said Barry Boss, a prominent white-collar criminal defense attorney. "Usually that's overwhelming in and of itself. So the notion of facing multiple indictments is just inconceivable to me."

Typically, defendants in federal cases are required to be present for significant events like initial appearances and verdict returns, but they have leeway in deciding when else to appear.

"Some people are very involved in their defense and want to speak with you every day, while others leave it up to you and make themselves available when needed," Boss explained.

These investigations also dominate Trump's campaign spending. This year, his political operation has spent more on legal fees to defend him, his staff, and allies than on travel, rallies, and other campaign expenses combined, according to an AP analysis.

Generally, sitting presidents are shielded from indictment and criminal prosecution under Department of Justice guidelines. However, winning back the White House would not provide Trump with indefinite protection.

If reelected, he could direct his attorney general to dismiss federal cases, fire prosecutors, or push the limits of presidential power by attempting to pardon himself. However, these efforts would only apply to federal cases, not the state criminal charges in New York or potentially Georgia.

Even if Trump does not secure the nomination, a different Republican president would likely face intense pressure from Trump to drop the charges to appease his supporters — a pressure no president has encountered since Gerald Ford pardoned Richard Nixon for Watergate crimes.

In total, "It's extraordinarily bad news, and the international impact would be devastating. That's why people need to come to their senses," said John Bolton, Trump's former national security adviser and critic. He believes this reality intensifies the pressure on Republicans to find an alternative candidate. "Someone needs to take the initiative and say we are heading off the edge of a cliff here."

But so far, Trump has experienced limited political consequences from his indictments; his lead over Republican challengers has even grown as they struggle to respond. Simultaneously, he has used the prospect of jail time to raise funds.

In a recent fundraising email, he complained about the "Department of 'Justice'" attempting to put him in jail for life as an innocent man. Other solicitations have arrived with subject lines like "re: 400 YEARS in prison."

Fleischer stated that voters will interpret Trump's legal victories and losses through the lens of the campaign.

For instance, if charges in one case are dismissed, "it will be like he won this legal primary," and if a judge rules against him, "people will feel like he lost the first day of the court primary."

Fleischer also suggested that if Trump ends up spending significant time in court, he can envision the former president speaking on the courthouse steps, telling viewers at home, "I'm not the one on trial, you are. And I'm in this courtroom fighting for you."

"It might take him off the campaign trail, but he has another platform to have his voice heard. To him, it's all part of the same campaign."