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Is Donald Trump’s Luck About to Run Out in a Manhattan Court?

While Fani Willis deliberates and Jack Smith investigates, E. Jean Carroll finally gets her day in court.

Francis Wilkinson

April 25, 2023

E. Jean Carroll attends the 2019 Glamour Women of the Year Summit.(Astrid Stawiarz / Getty Images for Glamour)

It’s a tabloid banner day in Manhattan today as jury selection begins in E. Jean Carroll’s civil suit against Donald Trump. Carroll’s case, accusing Trump of sexual assault in a Manhattan department store dressing room in the 1990s, serves as a bookend to the Access Hollywood tape, which cemented Trump’s reputation for both sexual assault and immunity to consequences. But it also raises the question: Will Trump slither away again?

Despite a decades-long history of fleecing contractors on his building projects, diverting charitable contributions to his personal use, and defrauding students at his bogus university, Trump avoided arrest until earlier this month, when he showed up for his New York arraignment in the case of falsified reports of a hush-money payment to a porn star, a matter that is arguably the Trumpiest concoction of them all. Many people, including The Nation’s Elie Mystal, believe that the legal scaffolding for that prosecution is shaky, and that Trump is likely to wriggle out of other legal difficulties as well. After all, The New York Times once accused Trump of committing “outright fraud,” and backed it up with thousands of words of documentation. Nothing happened.

Yet, with criminal investigations in Atlanta and Washington, D.C., soon reaching their decision points, Trump’s crime spree may not keep paying quite so well. Trump has proved unable to fool all of the people all of the time. Can he really beat all the raps all the time?

Trump has always been an expert circus performer. However, he typically fares less well in the venue where crimes are prosecuted: the courtroom. Trump has a long record of fails in court—both as plaintiff and defendant. His 62 cases seeking to overturn the 2020 election results, many of them before judges he appointed himself (or at least pretended to), were abject failures. His defamation lawsuit against journalist Tim O’Brien provided no purchase against O’Brien’s reporting that Trump’s highly leveraged empire was a gaudy mirage. O’Brien’s lawyers exposed Trump as a liar and fantasist who established his net worth based on his own woozy “feelings.”

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In 2018, the attorney general of New York sued the Trump Foundation, citing a pattern of misconduct. By the end of 2019, the faux foundation was shuttered and Trump was ordered to pay $2 million to charities. The state’s lawsuit against Trump’s skeevy “university” reached a similar end, with the scam shut down and Trump paying out $25 million in restitution.

Trump’s reflexive lying is not a useful talent in the legal system. Neither is grievance-mongering, blame-shifting, whataboutism, misogyny, racial aggression, ad hominem attacks, or other Trump core competencies. Courts are partial to facts, which have never been partial to Trump. Courts likewise reward preparation, discipline, and coherence, which can help steer fact patterns onto favorable terrain. Trump, by contrast, is a notoriously sprawling mess. Out of one side of his mouth he shouts that the classified documents found at Mar-a-Lago are his rightful property, while out of the other he claims they were planted by the FBI. If you’re looking to establish consciousness of guilt, it’s hard to beat declaring that the papers taken from your office were planted by the deep state. Crooked cops, after all, don’t plant evidence of innocence.

Perhaps the prosecutors investigating Trump in New York, Washington, D.C., and Atlanta will all prove to be incompetent bumpkins. But that seems unlikely. Even Alvin Bragg, the Manhattan district attorney who is generally perceived to have the weakest hand, is acutely aware of the stakes. For better or worse, this case will define his career. Would he have indicted Trump on only the flimsiest of proof? Possibly. But I wouldn’t bet on it.

Trump’s current predicament calls to mind the right-wing scammers who made long careers propagating baseless allegations of election fraud. Kris Kobach, Hans von Spakovsky, and others had a consequence-free run—until the ACLU brought a lawsuit against a Kobach-promoted voter law in Kansas. With witnesses under oath, handcuffed to facts, Kobach was publicly humiliated in the process of losing the case. Similarly, it was the threat of testimony under oath that threw a $787.5 million wrench into Rupert Murdoch’s lie factory earlier this month.

Trump will be tried in at least one jurisdiction where red caps are not much in demand. Having backed himself into a corner with a litany of lies, he can’t strike a plea deal without it being accurately perceived as surrender. And if he hopes for rescue by the Supreme Court, one-third of which he installed, he may discover that the right-wing politicos on the bench are ingrates. If they have to choose between saving Trump’s bacon, or ridding their party of an electoral anvil, the bacon is, well, toast.

How sure am I that Trump will face the music? It’s 2023. I’m not sure the sun will rise tomorrow. Obviously, Robert Mueller, who amassed overwhelming evidence of Trump’s criminal obstruction, failed spectacularly. But Mueller was boxed in by both Justice Department policy and a corrupt attorney general, and his effort was undermined by the entire political stratum of a Trumpified Executive Branch.

Trump lacks all such advantages now. Much of his malfeasance took place in public or before witnesses. Any cases brought against him are more likely to be strong than weak, while his defenses are more likely to be weak than strong. The mundane reality is that the legal system convicts bad guys all the time. There are many exceptions. But perhaps, at long last, Trump will not be one.

Francis WilkinsonTwitterFrancis Wilkinson writes about politics for Bloomberg Opinion. He has written for The New York Times, Rolling Stone, and many other publications.


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