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Trump’s Day in Court (and Court and Court and Court)

Major developments in several of the ex-president’s legal battles, as he keeps trying to dodge, duck, dip, dive, and dodge.
November 23, 2022
Trump’s Day in Court (and Court and Court and Court)
Former Trump CFO Allen Weisselberg enters the courtroom in Manhattan Supreme Court this past summer. (Photo by Curtis Means / AFP / Getty)

Given all the headlines about the new special counsel taking over the federal investigations of Donald Trump’s criminal involvement in January 6th and his storage of classified documents at Mar-a-Lago, it’s easy to lose track of his many other legal battles. But this week brought a veritable pu-pu platter of court convolutions for the ex-president. Let’s catch up.

For starters, the Manhattan district attorney’s office is winding up its three-week criminal trial against the Trump Organization, which it charged with nine counts of wrongdoing, ranging from tax fraud and conspiracy to falsifying records. Longtime Trump aide Allen Weisselberg testified on behalf of the government regarding the apartments, luxury cars, and private-school tuition for which off-the-books payments were made. The legal question for the jury is whether the Trump Organization—a corporation that of course cannot go to jail but could, if convicted, be hit with $1.6 million in fines and barriers to obtaining creditors and business partners—is liable, or instead the blame falls on Weisselberg personally and on outside accountants such as Donald Bender, the Mazars USA partner who worked on Trump’s tax returns. The prosecution declined to call Bender as a witness, and he instead testified for the defense on Tuesday, asserting that Weisselberg never told him about the perks he received from the Trump Organization. For the prosecution to lose the case, the jury will have to buy the notion that none of this was done “in benefit of” the company, even though Trump is the sole or principal owner of the over 500 businesses known collectively as the Trump Organization.


Also on Tuesday, three judges on the U.S. Court of Appeals for the Eleventh Circuit heard oral argument on Trump’s claim that a special master is needed to oversee the FBI’s review of the nearly 22,000 documents seized from Mar-a-Lago in August. Three things to keep in mind here. The first is that Trump already resoundingly lost his argument before this court as to classified records, which the court released to the FBI and the Department of Justice in September, reversing the lower, district court’s bizarre ruling to the contrary.

The second is that no one but Trump would come close to receiving the kid-glove treatment that he has received in these proceedings; normally, once a warrant is authorized by a judge under the Fourth Amendment to the Constitution (as happened here), the government holds the cards. Nobody gets to stop the government from pursuing a criminal investigation altogether. Trump did.

The third is that Trump’s complaints are easily rectified—he asserts that some materials are protected by attorney-client privilege or are personal, not presidential, records. DOJ undoubtedly filtered this stuff out long ago. So the Trump drama is much ado about very little legally. Which is why Judge William Pryor, a George W. Bush appointee, pushed back on Trump’s hair-on-fire arguments on Tuesday: “We’ve got to be concerned about the precedent that we would create that would allow any target of offense of a federal criminal investigation to go into district court and to have [it] entertain this kind of petition . . . and interfere with the executive branch’s ongoing investigation,” he said.

I’m going to go out on a limb here and predict that Trump will lose this one. The battle is nonetheless significant because Special Counsel Jack Smith’s jurisdiction includes this investigation. As it stands, he cannot use any of the documents seized to further the investigation or craft indictments (save classified records). When the Eleventh Circuit rules against Trump, it’s going to light a fire under that probe, which Trump has managed to stall for months.

The next spot of legal news involves New York Attorney General Letitia James’s civil fraud case against Trump, which alleges that Trump, his three children, and a slew of his organizations—plus Weisselberg—duped banks and insurance companies over 200 times by grossly inflating assets over a decade by billions of dollars. Earlier this month, James persuaded a New York state court judge that the defendants might be moving assets in the interim. The court thus barred such activity absent court approval, required the inclusion of supporting documentation in any new financial disclosures to banks and insurers the defendants make, and ordered the appointment of an independent monitor to ensure Team Trump complies throughout the litigation.

Meanwhile—and this one is amazing even by Trumpian standards—his team filed a lawsuit in Florida state court seeking to block the progress of New York’s case, claiming it invades his privacy rights to a revocable trust that holds Trump Organization assets in his name. Not only is James “guided solely by political animus and a desire to harass, intimidate, and retaliate against President Trump,” his Florida lawyers argue, but she was able “to hand-pick the New York state court judge to rule on her request to seize control of the Trump business empire.” That business empire includes “highly valued real estate and other assets, minimal debt, and brand value which, if properly managed and run, is virtually incalculable.”

What’s also incalculable is the audacity of asking a Florida court to interfere with a New York judge’s jurisdiction over a case brought by the State of New York under New York law. It’s why some of Trump’s more sober lawyers reportedly argued strenuously against the filing, which surely borders on malpractice. Trump’s ego appears to have won the day. “As a private company, nobody knew very much about the great business that then-businessman Donald Trump had built but now it is being revealed by James and much to her chagrin,” the complaint states triumphantly. The government managed to transfer the case to federal court (in a process that’s technically known as “removal”). Trump will surely lose this one, too.

Last is the pesky defamation lawsuit filed by E. Jean Carroll, who claims that Trump raped her in a high-end Manhattan department store in the 1990s and then called her a liar once she made the incident public. Trump was forced to testify in a deposition in August. Trial is scheduled for February. Trump lost his threshold bid to toss the suit out altogether. Under former Attorney General Bill Barr, DOJ sided with Trump in arguing that his comments were immunized by virtue of having been made while he was president. Trouble is, he is president no more. (The judge also rejected the strained argument that Trump was performing presidential duties when he made statements about Carroll.)

The latest wrinkle is that in May, New York passed the Adult Survivors Act, which reopened the statute of limitations for otherwise stale sex abuse cases for one year. Carroll’s lawyers accordingly want to move the trial to April and add a battery claim. Trump’s counsel is balking, arguing (understandably, frankly) that a jury could be biased against the defendant if it hears the battery claim alongside the defamation one. Either way, he’s going to trial on a rape allegation; the defense to defamation is truth. (Cue the Johnny Depp and Amber Heard trial.)

All told, and despite his decades-long track record of using the courts successfully to his advantage, Trump’s legal luck is changing. He is not “special” anymore. His feverish dodging and weaving seems increasingly futile—and desperate. The rule of law applies to him like everyone else. Although the gears of the legal system grind frustratingly slow at times, it’s hard to dodge forever a process that is bounded by facts and law—and, in its best moments, justice.

Kimberly Wehle

Kimberly Wehle is a contributor to The Bulwark. She served as an assistant U.S. attorney and an associate independent counsel in the Whitewater investigation. She is currently a professor at the University of Baltimore School of Law. An ABC News legal contributor, she is the author of three books with HarperCollins: How to Read the Constitution—and Why, What You Need to Know About Voting—and Why, and, most recently, How to Think Like a Lawyer and Why—A Common-Sense Guide to Everyday Dilemmas. Her new book, Pardon Power: How the Pardon System Works—and Why, is forthcoming in September 2024 from Woodhall Press. @kimwehle.