“He sued for sport; he sued to achieve control; and he sued to make a point. He sued as a means of destroying or silencing those who crossed him,” Zirin said in an interview.

But for all of Trump’s time in the docket, his involvement in legal proceedings has all been of the civil variety. No longer. He’s now facing two criminal prosecutions, a business records case in New York state, and the 37-count federal indictment filed against him Thursday alleging that he removed and retained classified documents when he left the White House. As Trump is about to learn, there’s a big difference between a civil proceeding, which he knows intimately, and a criminal trial. It’s like the difference between a flickering candle, which can raise a blister if you’re not careful, and a forest fire, which can reduce you to ash. Trump’s legal hubris, acquired in decades of civil litigation, has blinded him to the danger he is in. If he really knew courts as well as he claims, he would have done everything possible to avoid at least three more potential cases — for tax fraud, election meddling and interfering with the lawful transfer of power.

The criminal indictment of a former president who happens to be the leading Republican aspirant for the White House is unprecedented territory for the country. But it’s perhaps more important that this is unfamiliar terrain for Trump as well, and he has not prepared properly for the ordeal.

The biggest practical difference between civil and criminal prosecutions is that remedies in civil cases are financial penalties or injunctions. This is the padded playroom in which Trump has cavorted his entire professional life. To Trump, lawyer fees, monetary punishments and court orders — when cases come to that — are just the costs of doing business. Trump’s legal guru, Roy Cohn, taught him to draw out civil cases, wear the other side down, and never give in, a catechism that still guides him today. As Zirin puts it, Cohn taught Trump to counterattack; undermine his adversary; work the press; lie, lie and lie again; and even in the case of a loss or forced to settle, claim victory and go home.

But 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. Trump has already invoked the Cohn rules in the federal indictment, accusing prosecutors of election interference and the Biden administration of judicial corruption. He’s fund-raising off the indictment, too, and using it as a plank in his campaign platform. “They’re not coming after me, they’re coming after you — I’m just standing in their way!” reads the pinned message on his Truth Social account. But the Cohn rules, which can work so brilliantly in civil court, don’t carry the same weight in criminal cases. 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?

They probably did. But remember, this is the guy who was told by an aide not to look into the sun during a solar eclipse, and he did it anyway. His lawyers have probably told him to shut up, too, but if so, he’s already ignored that cardinal bit of defense advice. As he continues to attack the prosecution, will he divulge more potentially incriminating comments, as he did several times during the recent CNN town hall.

Of all the criminal proceedings and investigations against Trump, the one that would have been easy for him to avoid is the classified documents case. If, when contacted by authorities, he had simply returned the documents, he would have suffered not at all, like Joe Biden and Mike Pence, who quickly complied when their poor document hygiene became known. Trump’s problem is that he would rather fight the law even when there is no reason to fight. He turned down multiple opportunities to return the docs. Instead, he prevaricated with a grin as if he were dodging some New York City building inspector. For his defiance, he might go to jail. According to the penalty sheet in the indictment, Trump faces 100 years if convicted on all 37 counts. That’s not how it works, but it gives you a thumbnail of the peril he’s in.

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. His trial dates are months and months distant. It would be a legal miracle to try all the cases — both filed and prospective — before the 2024 election. He must figure he can retake the White House, which, depending on what the Supreme Court says, will give him leverage to postpone his trials. He might also believe that Ron DeSantis will pardon him, which DeSantis has not ruled out. (Presidential wannabe Vivek Ramaswamy has already committed to a pardon, so Trump has that going for him.) A self-pardon has never been tested, but Trump could theoretically take that route and negate federal convictions upon returning to the White House. But he’d still be on the hook for the state offenses, which are not pardonable by the president.

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.

The Cohn rules have taught him lessons that seem to be pointing to his final undoing.

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Trump fought the law. Will the law win? Send your favorite Bobby Fuller Four recommendations to [email protected] and tell me how much you miss Buddy Holly. No new email alert subscriptions are being honored at this time. My Twitter feed’s favorite BF4 song is “Let Her Dance.” My Mastodon, Post, and Substack Notes accounts don’t rock. My RSS feed favors the Dead Kennedy’s revisionist version of “I Fought the Law.”