Trump lawsuits: Some get delayed. Some prove costly.

The outlook for former President Donald Trump’s legal troubles is beginning to look very different than it did only a few months ago.

Civil trials that many legal experts once rated secondary to his upcoming criminal prosecutions have begun to hit Mr. Trump hard in the wallet. Two convictions for defamation against writer E. Jean Carroll will cost him some $88 million, unless the awards are reduced on appeal. He will likely be on the hook for hundreds of millions more after New York state Justice Arthur Engoron, who has already found the Trump family business liable for financial fraud, rules on penalties in that case.

At the same time Mr. Trump’s big criminal trials are appearing increasingly less likely to produce verdicts prior to the 2024 presidential election. Less-than-speedy judicial decisions have pushed back federal proceedings charging him with trying to overturn the 2020 vote and illegally retaining classified documents. In Georgia, charges that the prosecutor hired a romantic partner have muddied prospects for that state’s sweeping election interference case.

The bottom line is that Mr. Trump’s legal strategy of attempting to drag out cases to lessen any political impact on November’s election could be working.

“He has been remarkably successful thus far at delaying his criminal trials,” says Daniel Urman, a professor of law and public policy at Northeastern University.

Expensive civil cases

For Mr. Trump, the potential outcome of the civil cases has always seemed less dire than the possible consequences of the criminal proceedings. Civil cases don’t result in jail sentences. Instead, they typically produce monetary judgments.

But the size of the award against the former president in the Carroll defamation case, along with what may be an even larger judgment in the New York state fraud case, could pinch the finances and cash flow of even a wealthy real estate magnate.

Late last month, a federal jury awarded Ms. Carroll more than $83 million in damages for defamation after she accused Mr. Trump of sexually assaulting her decades ago in a department store dressing room. He had denied the charge, and attacked the writer in bitter, personal terms.

This sum is stacked onto $5 million Ms. Carroll won from Mr. Trump last year in a related legal proceeding.

While these judgments will almost certainly be appealed, Mr. Trump under New York law will have to either produce the entire sum to be held in trust while the appeal proceeds or post a bond equal to the amount.

Meanwhile New York state Attorney General Letitia James is asking for a $370 million judgment against Mr. Trump and co-defendants for exaggerating his firm’s wealth to lenders. Judge Engoron has already ruled the defendants are guilty in this case. He is planning on issuing a ruling on the size of penalties by mid-February.

“That’s the working timeline,” said Alfred Baker, a spokesperson for New York’s Office of Court Administration, last week.

A total of half a billion dollars in civil judgments would not bankrupt the billionaire Mr. Trump. But it could drain his ready cash and force the sale or mortgaging of real estate assets.

“I believe we have substantially in excess of $400 million in cash, which is a lot for a developer,” said Mr. Trump in a deposition last year for the Carroll case.

Mr. Trump’s presence at the civil cases this year greatly increased media coverage and public awareness of the proceedings. His use of the courtroom as a quasi-stage to express discontent perhaps presaged the approach he may use if his criminal cases come to trial.

In the Carroll courtroom, Mr. Trump glowered, whispered loudly to his attorneys, and finally stalked out entirely during the summation by Ms. Carroll’s attorney Roberta Kaplan.

His behavior was “his way of sending a message to the jury and creating a circus,” tweeted former federal prosecutor Renato Mariotti on Jan. 26.

If so, it apparently did not work, as the jury returned its verdict of an $83 million judgement within a few hours.

Slow criminal cases 

Mr. Trump’s evident desire to stretch out his criminal trials as long as possible has been more successful.

“He has absolutely used the opportunities available to him to the fullest in that way,” says Professor Urman. 

Trump critics have hoped these trials might deliver a final blow to the former president’s Oval Office hopes. That remains possible, but it now seems at least as likely that the most important of these cases will not wrap up before November.

If they do not, and Mr. Trump triumphs, upon his inauguration he is almost certain to order the Justice Department to drop the cases brought by special counsel Jack Smith – the federal election interference case and the prosecution for hiding classified documents at Mar-a-Lago after leaving office.

Perhaps the most important current source of delay is the question of presidential immunity that Mr. Trump’s lawyers have raised in regard to the election case.

They argue that Mr. Trump, as a former president, is immune from criminal prosecution for acts taken while in office if he is not first impeached and convicted by the Senate for those acts.

The case, under Judge Tanya Chutkan, has been paused for 50 days while this question is litigated. It is currently under consideration by a panel of the DC Court of Appeals and will almost certainly end up in the Supreme Court.

Originally, the trial in the election case was scheduled to begin on March 4. That date has now dropped off the public calendar of the federal court in Washington. It is unclear when the case might resume.

The federal classified documents case has similarly slowed following a relatively brisk beginning. Judge Aileen Cannon, a Trump appointment to the federal bench, has run pretrial proceedings at a relatively leisurely pace. And any case in which litigation revolves around classified information is complicated, involving lengthy discussions among defense, prosecution, and judge as to what secrets can be used at trial, and how they should be handled.

The documents case is still scheduled to begin on May 20, but many legal experts doubt that deadline will be met.

Meanwhile, whether the Georgia election case will proceed on schedule is now up in the air, as a state judge weighs whether prosecutor Fani Willis should be removed from the case following reports of her romantic relationship with a subordinate. 

The only Trump criminal trial that appears to be still on track is one in New York state that centers on charges involving Mr. Trump’s payment of hush money to adult film actress Stormy Daniels prior to the 2020 election. That involves a novel interpretation of state law that prosecutors have used to charge the case as a felony.

“Trump prosecutions are no longer on pace to finish before the election, with the least important New York case now most likely to move in time,” wrote Michigan State University political scientist Matt Grossmann on X, formerly Twitter, last week.