During the 2016 Presidential campaign, crowds at Donald Trump rallies upon hearing the name of Democratic nominee Hillary Clinton would inevitably break out in chants of “Lock her up! Lock her up!” as Trump nodded his head in agreement.

Now seven years later, with Trump under criminal indictment in two federal and two state-level cases, it is the former president who faces the very real possibility of being the first former U. S. President sent to prison.

Trump is charged with trying to illegally overturn the results of the 2020 election both in a federal case and in a sprawling Georgia conspiracy case where he’s been charged along with 18 co-defendants. Trump also faces federal charges for illegally possessing and storing classified national security documents at his Florida estate. Finally, in a New York case Trump is charged with falsifying business records to conceal hush money payments to a porn star.

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Illinois legal experts weigh in

Legal experts we spoke with agreed the New York case is the weakest, and probably will be tried last. But the two January 6th cases and the classified documents case place Trump in significant legal jeopardy.

“The documents case is the most straightforward one, in terms of proof,” said Joseph Ferguson, a former assistant U. S. attorney. “Their defense is arguing that the Presidential records act allows them to keep stuff and by merely thinking something he has declassified it. Both of those notions are non-starters. It’s just not the law. That’s the cleanest case.”

“The official secrets case is much simpler but also would be far less likely to yield jail time,” said Ronald Safer, a former assistant U. S. attorney. “Biden had classified documents. Pence had documents. Bill Clinton had documents. Now they don’t do it willfully. They don’t try to obstruct and when it’s brought to their attention, they give the documents back. Still, I doubt that’s something that’s going to send him to jail. But I would be very surprised if he did not get jail time if he’s convicted for subverting the democratic process.”

“It’s what separates our government from dictatorships and monarchies,” Safer continued. “If the voters’ decision is subverted by those in power that’s a fundamental challenge to our government. And if somebody who subverts that process does not get jail time then what non-violent crime will?”

Former Illinois House Minority Leader Jim Durkin also sees the classified documents case as the strongest of the four indictments and believes federal judges will not be reluctant to send Trump to prison.

“I think it’s going to be very difficult for a judge not to send the former President to a term of incarceration in the federal prison system,” said Durkin, a former Cook County prosecutor. “He should not be treated any different than anyone else who had been charged. These are not probation able cases. The question is how deep and how damning the evidence is that is recovered. But you’ve heard him talking about war plans, waving around the invasion plan for Iran in front of giggling women. It’s consistent with his behavior where he believes he’s above the law and can do whatever he wants.”

Trump faces the possibility of considerable prison time if found guilty in the federal cases. Thomas A. Durkin, a former federal prosecutor with extensive experience in national security law, estimated that under federal sentencing guidelines, if found guilty in the official secrets case Trump would face “a sentence of 51 to 63 months at the low-end, best-case scenario, and in the worst case, which I’m not sure would apply, 210 to 262 months.” In other words, a sentence of just over four years to nearly 22 years.

What’s more, in the federal election subversion case, said Thomas A. Durkin, “I’ve been involved in enough January 6th cases to know the sentencing would be very high. Very, very high. We’re talking about double-digits in years of imprisonment.”

Which is why, despite his defiant public face, Trump has to be sweating.

“Donald Trump’s only defense to these federal cases is to win the Presidency,” said Jim Durkin. “I’m convinced that’s the major reason he’s running. I believe that’s his goal. He wants to get elected and pardon himself. That would get him clear of a federal prison sentence.”

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Impact of Georgia case against Trump

Legal experts differ on whether a President can pardon himself of a federal criminal conviction. However, if that is the Trump strategy, the Georgia indictment complicates matters because a President cannot pardon anyone of a conviction in state court.

The Georgia indictment is problematic for Trump in other aspects as well. At least two Trump co-defendants, former Trump attorneys Sidney Powell and Kenneth Chesebro, have asked for a speedy trial, which is at odds with Trump’s self-admitted strategy of delaying the trial as long as possible. 

“That signals the trials will be split up in some way. No way you’re going to see 18 defendants tried alongside Trump. There’s not a courtroom big enough to handle all the lawyers for that. So, there’s going to be an early trial or two. And you’re going to probably see people pleading guilty to a lesser charge, like lying to investigators,” said Ferguson.

“And in the Georgia case there’s a minimum mandatory sentence of five years under the RICO law. Five years. So going to trial knowing that sentence looms, that’s a big roll of the dice. I expect to see a lot of the lower-level defendants cooperating, trying to cut a deal to testify against the bigger fish,” said Thomas Durkin.

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Issues with imprisoning a former U.S. President

If Trump is sentenced to prison, another long list of issues presents itself. Speaking off the record, a former high-ranking official of the U.S. Marshalls Service told me the decision of where to imprison Trump “would be made at the very highest level of the Department of Justice due to the notoriety of the defendant and the potential security concerns.” Which means the decision would be made or at least carefully reviewed by the U. S. Attorney General.

Non-violent white collar criminals generally get sent to minimum-security federal “prison camps” without guard towers, barbed wire or cells where inmates bunk in dormitory style rooms. “If the Bureau of Prisons did not think he could reside there, do his time there, based on their ability to provide the correct amount of security they’d have to make other arrangements. He’s a tough one because the camps may not provide the right security needed to house him,” said the former U.S. Marshalls official.

“The most complex scenario is assigning him to a low to mid-level facility where he is in the general population and now you’ve got to provide for his security in a somewhat fluid situation. If he’s held in isolation, say in the Supermax prison in Florence, Colorado, it’s way easier to protect him. It’s that middle ground that’s complicated,” said Joseph Ferguson.

According to Ron Safer, there is no inalienable right to Secret Service protection for former Presidents. “The statute says that the Secret Service is authorized to protect former Presidents. The Secret Service determines what is necessary to protect the former President,” said Safer.

“The Secret Service is responsible for the security of the President, but it has lots of latitude to assure that,” said Ferguson. “So, the Secret Service largely would be directing overall security in collaboration with officials of the Bureau of Prisons. They would work all of this out.”

Ferguson pointed to a situation involving Hillary Clinton, a former First Lady who also received Secret Service protection. When she became Secretary of State, the Secret Service turned over those protection duties to the State Department. “The Secret Service does not have to provide physical protection, they only have to oversee it,” said Ferguson.

But with a conviction for inciting the very violent January 6 insurrection, would Trump be considered a non-violent prisoner?

“I think you might get a lot of pushback that the January 6th case is not a crime of violence,” said Thomas A. Durkin. “I think it most certainly is. That brings into play not just the sentencing considerations because it is a crime of violence but also whether Trump continues to subtly threaten or encourage violence.”

As an example, Durkin pointed to an online interview with Tucker Carlson in which Carlson first asked if we’re moving toward Civil War and then “You think it’s possible there’s open conflict?” Trump replied, “I don’t know. I don’t know. I can say this. There’s a level of passion I’ve never seen and there’s a level of hatred I’ve never seen. That’s probably a bad combination.”

In Durkin’s view, Trump is clearly hinting of or threatening street violence if he is imprisoned. “What’s at stake in my opinion is whether you’re going to permit the fear of civil unrest or civil violence alter what most people would consider a republican form of government under constitutional rule of law. Because if you make an exception out of fear of civil violence, that’s it, the game is over,” said Durkin. 

“Usually there is a fear by criminal defense attorneys or their clients that if you don’t shut up, you’re going to be detained pre-trial. And what Trump is pushing up against comes from the fact that he knows it is unlikely in the extreme that he will ever be detained pre-trial, especially while running for President. So, he is just going to push and push and push,” said Ferguson.

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Will jail time for Trump bring on civil unrest?

“I think we’re at a very dangerous point in time in this country,” said Thomas A. Durkin. “I think Trump is shrewd enough to have realized that and use it to his advantage. I personally think he’s going to use it to cut a deal. Because he’s smart enough to know he may well go to prison, and it may be for the rest of his life. I think he’s using the threats of violence as his get out of jail card. And that’s the card he’ll play.”

Ferguson ultimately anticipates a different denouement. “If Donald Trump is actually convicted of some of these crimes and a judge says jail time, I think the sentence probably gets commuted by a President regardless of whether a President is a Republican or a Democrat because the country doesn’t need it,” predicted Freguson.

“Trump and his team will continue to attempt to insinuate political motivation into every aspect of this. The prosecutors are politically motivated. The judges are politically motivated. He is attempting to undermine the reputation and integrity of the criminal justice system and will continue to do that by insinuating this is all politics, with violence as the lever that hangs out there, the Sword of Damocles that hangs over all of us,” said Thomas A. Durkin. “What is at issue for the criminal justice system is whether it can keep its focus on what its responsibility is. A dispassionate, fair administration of justice to come up with a fair resolution procedurally.”

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