Is Trump privately worried that he might spend time behind bars?

In late December 2023, former Donald Trump presidential staffer Alyssa Farah Griffin revealed that she believed Trump was running for office again because he was afraid that he might go to jail for the many federal and state crimes that he has been indicted on.

During an appearance on CNN, Griffin explained that she thought the fear of Trump's criminal cases was what drove him to run for office again and said that the former president worried about Special Counsel Jack Smith "in a big way" according to Newsweek's reporting on the interview.

Photo Credit: Wiki Commons By U.S. Department of Defense

Griffin also used a Christmas rant from the former president on his social media platform Truth Social to show just how much Trump was worried about Smith, and went on to note that the post was "kind of vintage Donald Trump."

"He is known for these kinds of unhinged holiday rants and then he follows up with a clip of him on Home Alone II," Griffin said. "Listen, it shows that Jack Smith lives in his head in a very big way. He is very concerned about the DOJ investigation into the events around January 6th. This is the driving force behind his political campaign."

Griffen went on to say that Trump's campaign team would have wanted his holiday message to be about the economy, jobs, or the country's foreign policy, but his messaging kept going "back to the fact that he honestly is worried that he will end up in jail."

"He needs to get elected president to pardon himself. So kind of his true colors are showing when he makes it all about Jack Smith and then puts a bow on it with the old 'rot in hell' at the end," Griffin added. However, this wasn't the first time the news media caught wind of Trump's worries.

In September 2023, Rolling Stone reported that the former president was very worried about spending time behind bars despite what he had been telling the media according to sources close to him who spoke with the news outlet 

The former president had four criminal cases pending against him at that time, cases which are still pending, and Forbes reported in August 2023 that all of his felony charges added up to a possible maximum sentence of 717.5 years, which is certainly something Trump should be worried about. 

717.5 years behind bars is a lot of time to spend in prison for a man who probably doesn’t have all that much time left. However, the idea of spending all that time behind bars didn't seem to worry Trump when he was asked about it. 

For example, the former president sat down with Meet the Press host Kristen Welker in September 2023 to talk about a wide range of issues, one of which was a question about the many criminal charges he faced. 

“When you go to bed at night, do you worry about going to jail?” Welker questioned the former president, who replied in his typical Trumpian fashion with his typical oafish mannerisms. 

“No, I don’t really. I don’t even think about it. I’m built a little differently,” Trump declared. “I don’t even think about it.” However, that might not have been the truth according to a different report at that time. 

According to Rolling Stone, sources close to the former president said he had privately asked about what could happen if he were sentenced. So it's possible his legal troubles really were starting to get to him in September. 

The magazine noted Trump’s private concerns over his possible future marked a major departure from the “private confidence” he had when dealing with his former legal troubles when serving in the Oval Office.

Trump allegedly wasn’t worried about what could happen with the Russian Inquiry since he didn’t believe he had done anything wrong according to one White House official who worked on the Mueller Investigation. 

“Not only was he convinced he had done nothing wrong; Trump was also aware of the Justice Department policy that a sitting president cannot be indicted while in office,” explained journalists Adam Rawnsley and Asawin Suebsaeng of Rolling Stone.

However, Rawnsley and Asawain reported that this time around Trump had been wondering aloud about “what life would be like if he’s convicted, and if appeals fail.” 

Three sources who are familiar with the former president’s private comments explained that Trump had been asking what a stay in prison might be like and what he would lose.

The former president has allegedly asked if he would be doing time in a “club-fed” style prison—something Vanity Fair translated to mean a white-collar prison.

Trump had also apparently inquired as to whether or not he would be allowed to serve his time at home and if his lifetime Secret Service protection would be taken from him. 

Finally, Rolling Stone noted that the former president has also pondered out loud about what he would have to wear if his political enemies ever actually got him behind bars. 

Unfortunately, all of Trump’s worries were relayed anonymously to the news magazine’s journalists. So it’s difficult to know just how scared the former president is when it comes to his criminal cases. But the evidence is mounting that he may in fact be worried about spending time behind bars.