Trump Claims Threat of Jail Time Does Not Bother Him

By Jerry McConway, updated on September 18, 2023

Donald Trump is now facing an onslaught of indictments, not to mention the civil trials that are also on the docket.

Aside from the massive financial implications of these trials, there is the real threat that Donald Trump could go to jail for the rest of his life.

Talking Points…

  • The cases against Trump
  • What Trump said
  • Will Trump go to jail?
  • My Two Cents…

The Cases

Donald Trump now has multiple civil cases against him that could eventually cost him hundreds of millions of dollars in losses, fines, penalties, and legal fees.

When you add in the indictments, Trump could end up with a legal bill of close to $1 billion.

The two cases that worry me the most are the January 6 case and the Classified documents case.

With the judges and jury pools that Trump will be facing, I don't see how he beat the four indictments without being found guilty in at least one case of at least one charge. It would be a miracle if he managed to get through these cases without at least one conviction.

What Trump Said

Trump sat down with Kristen Welker of NBC's "Meet the Press" last week to discuss the leadup to the 2024 election, including the idea that Trump could go to jail.

Welker asked Trump if he sleeps okay knowing that he could spend the rest of his life in jail after these trials.

He responded:

"I’m built a little differently, I guess, because I have had people come up to me and say, ‘How do you do it, sir? How do you do it?’ I don’t even think about it."

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

Will Trump Go to Jail

The honest answer is that he very well may go to jail.

As I noted above, it just seems unlikely that he will be able to navigate every single case successfully when you consider he is facing more than 90 indictments overall.

However, he is unlikely to go to jail anytime soon, regardless of when these initial cases wrap up.

If Trump is found guilty, his legal team will start the appeals process, and considering he was president at the time, every one of these cases is likely to end up before the Supreme Court.

I find it highly unlikely any judge would send him to jail until the appeals process is completed, so, technically, Trump could win the election, and serve as president, but at some point, he finds himself being sent to jail either while in office or after he leaves office.

My Two Cents…

I have said numerous times that legally, I think most of these cases are on very weak grounds.

What scares me to death, however, is Trump taking the stand.

He has given quite a few interviews as of late, and in several of them, if Trump answered the prosecutors' questions the way he answered the media questions, he would be implicating himself.

Trump gets very frustrated when people are challenging him, and his anger issues start to kick in, as was evident when he was talking to Kristen Welker and, to a point, Megyn Kelly.

Trump believes that when he says it, you are supposed to accept it as true, which will not happen in a courtroom.

He will not be able to deflect away and will be required to answer the actual question asked, which is likely to set him off when he is on the stand and trying to deflect from a question he wants to avoid.

As I mentioned above, Trump is very likely to lose at least one of these cases, but the appeals process is something else entirely, and he could win every case via the appeals process. Initially, however, I believe he will be found guilty in at least one case.

And keep in mind, for every case he loses, those legal bills continue to pile up during the appeals process.

About Jerry McConway

Jerry McConway is an independent political author and investigator who lives in Dallas, Texas. He has spent years building a strong following of readers who know that he will write what he believes is true, even if it means criticizing politicians his followers support. His readers have come to expect his integrity.

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