Is There a Price That Keeps Trump Quiet? E. Jean Carroll May Find Out.

How much money must E. Jean Carroll win to stop Donald J. Trump from talking about her?

A Manhattan jury last month ordered the former president to pay $5 million in damages, $3 million of that for defaming Ms. Carroll when he said her accusation that he had raped her decades earlier was a lie. The next day, Mr. Trump appeared on CNN, and again accused Ms. Carroll of making up her story and for good measure called her a “wack job.”

Now, Ms. Carroll is seeking millions of dollars more to stop the river of invective.

Forbes magazine says Mr. Trump is worth $2.5 billion, but his actual wealth is in much dispute — he has said his net worth fluctuates with his mood. As he seeks the presidency again, he has used his legal troubles, which include state and federal indictments, to raise money by tearing into prosecutors and plaintiffs.

Mr. Trump became a celebrity and then the nation’s chief executive largely through the power of an untrammeled tongue, creating fascination even among opponents with his unpredictable and cruel verbal assaults. He is also famous for his love of money, bragging about his fortune and flaunting its gilded prizes.

Ms. Carroll and her lawyers are trying to win a jury award that would bring his competing desires into economic equilibrium. But is there any amount of money that could persuade the former president to keep her name out of his mouth?

Ms. Carroll’s complaint will be heard as part of a trial scheduled for January, stemming from verbal assaults he made against her in 2019. Ms. Carroll has said she lost her job as an advice columnist for Elle magazine after those attacks and is seeking at least $10 million in compensatory damages for harm to her reputation. After Mr. Trump’s recent CNN diatribe, she said she also wanted “a very substantial punitive damages award” that would “deter him from engaging in further defamation.”

Ms. Carroll’s lawyer, Roberta A. Kaplan, said it was hard to put a number on that deterrence without knowing more about Mr. Trump’s financial position.

“What I do know is that Donald Trump cares a lot about money,” Ms. Kaplan said. “And here, the prospect that he could have to pay millions of dollars in punitive damages each time he defames E. Jean Carroll again has to weigh on his mind.”

Mr. Trump’s former fixer and lawyer, Michael D. Cohen, who helped Manhattan prosecutors build a criminal case against Mr. Trump over a hush-money payment to a porn star, said the calculation was primitive: “Donald is similar to a petulant child who continues to stick his finger in an electric socket, only to stop when it really, really hurts. In this case, it’s in his pocketbook.”

A lawyer for Mr. Trump, who has asked a judge to reduce the sum he already owes Ms. Carroll, did not respond to a request for comment.

Ms. Carroll drew Mr. Trump’s enmity in June 2019 after she first went public with her accusation that he had raped her in a Manhattan department store dressing room in the mid-1990s. Mr. Trump called her allegation “totally false” and said she was not his “type.” Ms. Carroll sued Mr. Trump for defamation for those comments in the case that is now scheduled for trial in January, after being stalled in appeals.

Last month’s verdict stemmed from a separate lawsuit, filed in 2022 under a New York law that allows adults a one-year window to sue long-ago sexual abusers. It, too, included a defamation accusation, because Mr. Trump last year had again called the rape accusation a hoax. The jury found him liable for sexually abusing Ms. Carroll, rather than raping her, and awarded her $2 million for that misconduct, plus $20,000 in punitive damages. It gave her $2.7 million for the defamation, along with $280,000 in punitive damages.

Given Mr. Trump’s comments on CNN after the verdict, the punitive damages clearly did not have the effect Ms. Carroll desired.

She went straight back to court. On June 13, the judge overseeing both cases, Lewis A. Kaplan of Federal District Court, let Ms. Carroll revise her earlier suit to include the fresh opprobrium.

Benjamin Zipursky, a Fordham Law School professor, said U.S. Supreme Court precedent has suggested that punitive damages should not exceed 10 times the compensatory damages. Using that as a guide, if Ms. Carroll obtained the $10 million in compensatory damages she seeks, a $100 million punitive damages award might be upheld.

Ben Chew, a Washington, D.C., lawyer, helped the actor Johnny Depp win a $10 million jury award from his ex-wife in a defamation case, with the former couple ultimately settling for $1 million to avoid further litigation. Mr. Chew said that because Mr. Trump’s liability for badmouthing Ms. Carroll was established in the recent trial, the only issue ahead is damages — “and how much would be required to deter recidivism.”

Because the punitive damages awarded last month did not muzzle Mr. Trump, Mr. Chew said, Ms. Carroll may wish to argue for several million dollars — “perhaps even to the eight and nine figures,” he said.

Or maybe it will require 10 figures, as shown by the success of one major defamation case.

Chris Mattei, a lawyer who last year helped the families of eight people killed in the 2012 mass shooting in Newtown, Conn., win $1.4 billion from Alex Jones, the Infowars conspiracy broadcaster, said the award “appears to have temporarily quieted Jones’s direct attacks on the families, though the harm from his decade of lies continues.”

“We needed to obtain a verdict that was substantial enough to get him to reassess his business incentives, believing that Alex Jones is primarily a profiteer,” Mr. Mattei said.

As for Mr. Trump, Mr. Mattei added, “he has political incentives right now that are at the forefront of his mind.”

Mr. Trump has often fought legal battles outside court, using them to win support from voters and making allegations that his lawyers have declined to repeat under oath. He has labeled Jack Smith, the special prosecutor who has leveled charges against him, a “deranged lunatic” and called Manhattan’s district attorney, Alvin L. Bragg, a criminal.

Those men could send Mr. Trump to prison, but Ms. Carroll’s case threatens only financial pain.

“Money has always been a decisive factor in his entire personality,” said James D. Zirin, a lawyer and the author of “Plaintiff in Chief: A Portrait of Donald Trump in 3,500 Lawsuits.” He added, “The amount of money that he has to pay out diminishes his power and diminishes his appearance as being this powerful Teflon Donald kind of figure.”

Mr. Trump has a reputation for stiffing people who work for him, from laborers to lawyers. But plaintiffs who win money have leverage like liens on real estate and mandatory financial disclosures.

One person who believes Mr. Trump is now likely to stop defaming Ms. Carroll is Barbara Res, a former top Trump Organization executive. Ms. Res said that since the recent 38-count federal indictment against Mr. Trump that accuses him of hiding classified records, his lawyers will be imploring him to cease and desist with the legal commentary. In layman’s terms: enough, already.

“I think that they will tell him to stop,” Ms. Res said, “and I think he now is in a position to listen.”

Anthony Scaramucci, who spent 11 days as the communications director in the Trump White House in 2017 and today is a harsh critic of the former president, said Mr. Trump’s repeated disparagement of Ms. Carroll was right out of his playbook — “double and triple down, never admit you’re wrong, never apologize for anything.”

“He’s like a washing machine,” Mr. Scaramucci said. “He has a spin cycle, he has a rinse cycle — then he has a repeat cycle.”

Susan C. Beachy contributed research.