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Donald Trump In Prison Is the Question That Should Make Your Brain Hurt

What would Donald Trump being in prison actually look like? To be frank, it raises so many questions a starting point is not easy to find.  

By Gage Skidmore. President of the United States Donald Trump speaking with supporters at a "Make America Great Again" campaign rally at Phoenix Goodyear Airport in Goodyear, Arizona.
By Gage Skidmore. President of the United States Donald Trump speaking with supporters at a "Make America Great Again" campaign rally at Phoenix Goodyear Airport in Goodyear, Arizona.

The historic and ignominious possibility of having a former president in prison raises questions as to what that could look like. Donald Trump doesn’t seem publicly fazed by it at this point.

Trump faces 91 counts in four separate venues including two cases for his effort to overturn the 2020 election and the subsequent Capitol riot on Jan. 6, 2021.

When asked by NBC News Meet the Press host Kristen Welker if he thinks about it, Trump responded by saying “I don’t even think about it. I’m built a little differently I guess.”

Would Donald Trump Live in a Plush Prison?

What would Donald Trump being in prison actually look like? To be frank, it raises so many questions a starting point is not easy to find.  

Rolling Stone raises the question as to whether he would retain his lifetime Secret Service protection and whether he would be sent to a “Club Fed” minimum security prison, he would be sentenced to house arrest in a plush location, or if he would be sent to a rougher prison setting.

“What would they make him wear, if his enemies actually did ever get him in a cell — an unprecedented set of consequences for a former leader of the free world,” Adam Rawnsley and Asawin Suebsaeng write in Rolling Stone. “What would happen — including in the Fulton County, Georgia criminal case against him and various co-defendants — if he were convicted and sentenced, but also re-elected?”

They continued, “The private questions are a departure from the air of supreme confidence invincibility Trump has projected. In interviews and elsewhere, he has claimed that the thought of losing in court and going to prison simply cannot enter his mind.”

Donald Trump Convinced He Will Avoid Jail

Yet that is not what Donald Trump is saying himself.

“I think it’s very unlikely,” Trump said. “What, what did I do wrong? I didn’t do anything wrong. You mean because I challenge an election, they want to put me in jail?”

The former president remains convinced he will be acquitted if not in the initial trial then on appeal.

“These are political, these are banana republic indictments,” he said. “I’ve been treated very badly.

“When you say, ‘Do I sleep?’ I sleep, I sleep. Because I truly feel that in the end, we’re going to win.”

Trump could end up being out on bail while awaiting his appeals. A conviction in the District of Columbia January 6 case is likely inevitable due to the demographic makeup of the city in which Trump won less than 10% of the vote and was widely reviled as president. The same will be true in Manhattan and likely in Fulton County, Georgia in which Trump won 26% of the vote in 2020.

Cases Against Trump Questionable

Many legal experts consider the charges in the Jan. 6, 2021, flimsy at best and rooted in constitutionally questionable legal theories. The Stormy Daniels case in New York even was panned by Trump’s nemesis former Deputy FBI Director Andrew McCabe.

“The question is whether what he did amounts to criminal offenses.…In fact, there is significant overlap in that case and Willis’ — the federal case includes the Georgia shenanigans but is broader because Trump’s schemes went beyond Georgia, seeking to reverse election results in additional battleground states won by Biden,” former federal prosecutor Andrew McCarthy wrote. “Smith’s problem is that the federal penal statutes he has invoked — relating to fraud, obstruction and civil rights — do not clearly and narrowly target the kind of conduct in which Trump engaged.”

McCarthy continued, “The special counsel will have to stretch the law and get favorable court rulings to make the charges stick. I am not convinced that he can (or at least that he should) prevail, but it’s a serious case.”

And McCabe suggested that there’s nothing there in the Manhattan case.

“I if I had to characterize it, it’s disappointment. I think everyone was hoping we would see more about the direction that they intend to take this prosecution. What is the legal theory that ties that very solid misdemeanor case 34 counts of misdemeanors to the intent to conceal another crime, which is what makes it a felony?” McCabe said. “It’s simply isn’t there. Now, it’s possible that the DA has an elaborate and solid theory that’s backed up by a lot of evidence, and he has just decided to conceal that at this point.” 

The only case that has any real legal merit to it is the Donald Trump classified documents case. There is not any subjectivity as with the Jan. 6, 2021 cases. The question is simple, “Did Donald Trump knowingly break the law and engage in the obstruction of justice?”

Even there, Donald Trump is liable to appeal to the U.S. Supreme Court based on presidential powers, and he could ask the court to invalidate the Presidential Records Act on constitutional grounds.

John Rossomando is a defense and counterterrorism analyst and served as Senior Analyst for Counterterrorism at The Investigative Project on Terrorism for eight years. His work has been featured in numerous publications such as The American Thinker, The National Interest, National Review Online, Daily Wire, Red Alert Politics, CNSNews.com, The Daily Caller, Human Events, Newsmax, The American Spectator, TownHall.com, and Crisis Magazine. He also served as senior managing editor of The Bulletin, a 100,000-circulation daily newspaper in Philadelphia, and received the Pennsylvania Associated Press Managing Editors first-place award for his reporting.

Written By

John Rossomando is a senior analyst for Defense Policy and served as Senior Analyst for Counterterrorism at The Investigative Project on Terrorism for eight years. His work has been featured in numerous publications such as The American Thinker, Daily Wire, Red Alert Politics, CNSNews.com, The Daily Caller, Human Events, Newsmax, The American Spectator, TownHall.com, and Crisis Magazine. He also served as senior managing editor of The Bulletin, a 100,000-circulation daily newspaper in Philadelphia, and received the Pennsylvania Associated Press Managing Editors first-place award in 2008 for his reporting.

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