Jack Smith

According to one political analyst, Donald Trump's rich history of involvement in civil lawsuits has given him a false sense of security as he faces real jail time should he gets a guilty verdict in any one of the 37 federal charges in his indictment.

In a column for Politico, Jack Shafer wrote that the former president has long boasted he knows the ins and outs of the court system after decades of civil lawsuits filed against himself and his Trump Organization.

Because of that, Shafer suggested the former president is in for a rude awakening when he is arraigned in Florida next Tuesday.

Writing that "Trump has been a party to so many legal actions — both suing and being sued," that he feels he has a handle on how to direct his attorneys to proceed, Shafer added that the former president's previous experience has "blinded him to the danger he is in."

Shafer added that civil suits are "the padded playroom in which Trump has cavorted his entire professional life," and he explained that jail time was never on the table with them. But now it is.

RELATED: Trump set for a 'brush with reality' if he attempts his favorite legal tactic with Jack Smith: former prosecutor

"Criminal cases don’t pit one person or organization against another. They are reserved for crimes against the state or society, and the plaintiff isn’t Joe or Doris or some regulatory body, it’s the big, angry fist of government. When you lose in this venue, you don’t write a check. You’re often sentenced to prison," he explained before adding, "Prosecutors seek justice, not compromise, and they’re relatively immune to the field disturbances that rattle civil litigators. Did Trump’s attorneys not tell him that?"

The analyst added that the newest indictment related to top secret government documents he refused to return could have been the easiest case to avoid by just complying.

"Inside his own bleached skull, Trump must now be imagining that he can run out the criminal clock too, just as he did in so many civil cases," he wrote.

He concluded, "A normal person would not assume they could win all four or five (or however many) criminal cases. A normal person would never put all his eggs in the single basket that says, 'Win the White House, Get Out of Jail Free.' A normal person would never count on DeSantis to deliver. And a normal person would never find himself in this pickle. But Donald Trump is not a normal person."

You can read more here.

As Donald Trump heads to a Florida courtroom to be arraigned on 37 federal counts ranging from conspiracy to violations of the Espionage Act, he and his lawyers may find that his favorite legal tactic won't work for him this time.

In a column for MSNBC, former U.S. Attorney Joyce Vance wrote that the flood of legal problems the former president has been mired in during his four years in office and since he lost re-election have caught the eyes of judges who are now more than aware of his penchant for delays and running out the clock.

As Vance wrote, Trump could be in for a rude awakening if he thinks he can delay the DOJ's case closer to the 2024 election or after with the hope he won't be prosecuted as a sitting president should he be headed back to the Oval Office.

According to the former prosecutor, Trump is headed for a "brush with reality."

RELATED: Judge Aileen Cannon put on notice by legal scholar to 'call it straight' at Trump's arraignment

After writing, "more recently, the courts seem to be catching on," she added, "Increasingly, the judiciary seems to be on to Trump. That’s bad news for his lawyers as they prepare for his arraignment. Tuesday will be Trump’s introduction to the federal criminal justice system. He will be called upon to enter a plea in court. The issue of pretrial detention will be resolved, and while the former president is likely to be released, he will have to arrange for a bond if one is ordered and obey any conditions of release the judge sets."

However, she wrote, "he will not be able to use frivolous tactics to delay, at least not if the trial judge is wise to Trump’s history."

Worst still for Trump is that any delays and legal maneuvers will be subject to scrutiny by judges on the 11th Circuit Court of Appeals which has previously observed Trump's act when they stepped in and overruled Judge Aileen Cannon when she issued very pro-Trump rulings in December of last year.

As Vance explained, "As a result, Trump may have already damaged his credibility with the judges who will now handle the first level of any appeals stemming from his case. That should mean Trump is unlikely to get away with the sort of borderline-frivolous moves that he has often attempted. He will have to make legitimate legal arguments. To the extent that he does not have them, he will be out of luck."

You can read more here.

United States District Court for the Southern District of Florida Judge Aileen Cannon was on the receiving end of advice from a noted legal scholar that she needs to handle the 37-count indictment of Donald Trump with care next week in light of her being "slapped down" the last time she handled a high profile case involving the former president.

Appearing with MSNBC host Ali Velshi, Harvard Law's Laurence Tribe called the allegations contained in special counsel Jack Smith's legal brief "jaw-dropping" and claimed Cannon -- who will likely oversee the initial hearing — needs to "call it straight" when making rulings.

Questioning how the Trump-appointed judge was assigned the case, Tribe told the host, "It's a little puzzling how she was chosen. The earlier case was not really a criminal case it was a civil suit brought by Donald Trump for the appointment of a special master, and the very conservative 11th circuit unanimously concluded she has no jurisdiction at all -— she was off the reservation — and the former president didn't even appeal that."

"Her earlier experience, if anything, doesn't count in favor of her handling this," he warned. "Maybe she is only handling the arraignment on Tuesday afternoon, but if she is appointed, then, I do worry that the degree to which she leaned over backwards in the direction of ruling for Trump, in ways even a conservative court slapped her down for and criticized her for, suggests that her loyalty may be somewhat more towards the guy who made her a federal judge, the one who appointed her, than to the Constitution."

"I hope that if she does what I recommended all your readers do and read this very concise and easy-to-read indictment — and she will, she will surely read , that even she will have a jaw-dropping experience, thinking, is that the guy who appointed me? Is this the guy on whose behalf I went out on a limb?" he added.

"Hopefully that will be her reaction, and she will go back to a normal judicial role and any normal judge with an indictment this strong, with evidence that comes straight from the defendant's mouth or from the mouths of his lawyers after a definitive adjudication of the attorney/client provision, any judge would really decide that it's important one way or the other that will be a verdict in this case before the next election so, the people of the United States know whether it is someone who is guilty of espionage, conspiracy to obstruct justice, and lying to the government with dangerous secrets of our national security -- whether that's the kind of person they want as president."

Adding that he hopes she won't make "dubious rulings," Tribe continued that he hoped she will "call it straight and, if she does, it's very hard to see what defense Donald Trump can present."

"You read it and your jaw drops and you get scared for the country," he said of special counsel Jack Smith's filing, "So, I'm hoping that despite the fact that Aileen Cannon would not have been my first choice as judge, it won't matter who the judge is, justice will be done."

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