No one knows more about manipulating this country’s legal system than Donald Trump. As a favored protege of the infamous and despicable New York lawyer Roy Cohn, who built a successful career ruining other peoples’ lives as Sen. Joe McCarthy’s ruthless sidekick in the 1950’s, Trump learned early on how to abuse the legal system as a tool of intimidation against his enemies.
For those unfamiliar with the sheer scale of Trump’s litigiousness, the title of a 2019 book by attorney James D. Zirin, “Plaintiff in Chief: A Portrait of Donald Trump in 3500 Lawsuits” says it all. As David Fahrenthold, in his 2019 Washington Post review of Zirin’s book, summarizes:
…Zirin argues that Trump learned to see the law as Cohn did: “not as a system of rules to be obeyed . . . but as a potent weapon to be used against his adversaries.” Trump sued often but rarely won big. Winning in court wasn’t always the point: The lawsuit itself was the thing, a tool of intimidation cloaked in legalese, an outgoing missile that left your enemies buried in costs and hassle. That approach had costs for Trump, too. But he could bear them. He lost friends, wives, lawyers and business partners — but always found new ones, who thought their fate would be different.
That lesson — to weaponize the legal process as much as possible — likewise applied whenever Trump found himself on the receiving end of litigation. Jack Shafer, senior media writer for POLITICO (also referencing Zirin’s account) notes that “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.”
However, as Shafer observes, the “Roy Cohn strategy” that Trump has so successfully employed in escaping serious civil liability over the course of his career does not translate well in the criminal arena, which is where Trump finds himself navigating today.
Shafer notes that “[T]he Cohn rules, which can work so brilliantly in civil court, don’t carry the same weight in criminal cases.”
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…[.]
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.
In short, if he hasn’t already realized it, Trump is soon going to find out that his favored tactics of wearing down the opposition with bluster, threats and expensive, crippling countersuits are simply inapplicable in a criminal setting. As Shafer observes, “Prosecutors seek justice, not compromise, and they’re relatively immune to the field disturbances that rattle civil litigators.”
In Shafer’s view, the biggest “tell” that reveals Trump’s over-arching, Roy Cohn-style mindset is the fact that he voluntarily put himself in peril in connection with the obstinate retention of those classified government documents. As Shafer notes:
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.
According to Shafer, what Trump failed to comprehend is that his reflexive, “I can get away with anything” attitude that’s worked so well for him over the past fifty years doesn’t provide the same options when the subject is criminal guilt or innocence. The opportunity to bury your opponent with onerous expenses (or just refusing to pay a judgment by filing for bankruptcy) is simply not a viable tactic, as it would be in a civil case. Nor is the opportunity available to appeal an adverse verdict with the strategy of negotiating it down, as often occurs in civil litigation. Trump can appeal any criminal conviction, of course, but unless and until that conviction is reversed, a convicted criminal he remains.
Even so, Trump may justifiably believe that he can steamroll an obviously biased Aileen Cannon, the Florida district judge currently presiding over the classified documents charges. Leaving aside whether he manages to negotiate a plea bargain in that case (a distinct possibility), it’s by no means certain whether Cannon would ever countenance a jail sentence. He also is unlikely to receive a trip to prison on the “hush money” case currently pending in the Supreme Court of New York, assuming he is convicted. While his guilt in both of those cases appears fairly patent, his exalted position as a former president may come into play in both circumstances.
But by summer’s end he will likely be facing at least two additional (and more serious) criminal indictments relating to his efforts to overturn the 2020 election, filed by Special Counsel Jack Smith as well as Fulton County GA prosecutor Fani Willis. Both of these prosecutors have demonstrated their relative indifference to Trump’s usual shenanigans, and both doubtlessly by now have been threatened so many times by Trump’s rabid supporters that they’ve likely been rendered impervious to any coercion or intimidation, public or private.
Of course, Trump thinks he can run out the clock, like he’s always done in civil matters. In fact, that appears to be his only strategy: To regain the White House, have a compliant and hand-picked Justice department dismiss all his federal criminal charges (but, significantly, not the state-based ones); or, if one of the cases actually sees trial before the 2024 election, perhaps throw his support behind a DeSantis or some other Republican in exchange for a promised pardon. But as Shafer points out, while certainly possible, none of these strategies are particularly attractive or even promising, particularly given the baggage that multiple indictments (or convictions) will carry with a majority of the voting public.
Rather, the fact that Trump finds himself in this predicament in the first place suggests that his reliance on Roy Cohn’s nefarious strategy and tactics may have finally exceeded its shelf life.