The lawyer who helped give us marriage equality may be Donald Trump’s biggest problem

Among the many lawyers who labored long and hard to make marriage equality a reality, Roberta Kaplan holds a special place. As Edie Windsor’s lawyer, Kaplan argued before the Supreme Court that the Defense of Marriage Act (DOMA) unfairly imposed a tax burden on Windsor when her partner died. The Court agreed, which was a huge victory for LGBTQ+ rights and paved the way for its decision two years later that made marriage equality the law of the land.

Now, Kaplan may hold another place in the history books. She may be the lawyer who sets Donald Trump on the road to political oblivion.

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That Kaplan is a lesbian makes the possibility that much sweeter.

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Kaplan has the distinction of having won two victories against Trump in the four high-profile legal cases that he’s currently facing. Not only did she get a jury to agree last fall that Trump sexually assaulted and subsequently defamed writer E. Jean Carroll, but she hauled Trump into court a second time for continuing his attacks on Carroll.

Trump’s lack of impulse control – or his arrogant belief that the law didn’t apply to him – cost him dearly. The first jury ordered him to pay Carroll $5 million. The second jury took just three-and-a-half hours to decide that Trump’s repeated attacks should cost him $83.3 million.

Whether Trump ends up paying anything like that remains to be seen. His attorney, Alina Habba, vowed to appeal. (Habba distinguished herself during the trial by having the judge repeatedly school her in Lawyering 101.)

But what Kaplan has done is remind voters just who Donald Trump is at a time when he can least afford it. The same week that Trump tried to lock down the GOP presidential nomination, he found himself in a courtroom, publicly humiliated because he had to obey the law.

Kaplan played Trump like a violin, largely by ignoring him. During his deposition in 2022, he went out of his way to insult her. He said that not only wouldn’t Carroll “be a choice of mine,” he gratuitously added, “I would not, under any circumstances, have any interest in you. I’m honest when I say it.”

If this was meant to wound Kaplan’s ego, it fell on deaf ears. All Kaplan said was, “I’m an attorney.”

During Kaplan’s closing arguments last week, Trump dramatically rose and left the courtroom, a breach of etiquette that the judge duly noted for the jury. If Trump thought that he was dissing Kaplan by walking out, he was also dissing the jury, who rendered their own opinion of him a short time later.

Meantime, Trump has now twice been found liable for damages for defaming a woman that he sexually assaulted. For anyone who has doubts about Trump – and it won’t take a huge margin to repeat his losses in battleground states – the verdict is a reminder of just how awful a person Trump is.

The verdict came at a time when Trump could least afford it. A lot of Americans are only twigging to the reality now that Trump will be the GOP presidential nominee. The same week that he declared victory in New Hampshire, he was hit with an unreal bill in New York.

The nice touch from Kaplan is that she used Trump’s own bragging about his wealth as the basis for seeking a big dollar amount.

As futile as her campaign is, Nikki Haley immediately knew the verdict was a chance to attack Trump. “Donald Trump wants to be the presumptive Republican nominee and we’re talking about $83 million in damages,” she wrote on X.

Haley may be beside the point, but she’s struck a nerve in the party. One sign that the MAGA universe is concerned about the implications of the verdict: much like the NRA going silent after a mass shooting, the right-wing media universe has been talking about pretty much every but the Carroll case.

“It will hurt with independent voters in November,” Alice Stewart, a Republican strategist, told Politico.

Trump’s biggest mistake was in thinking that Kaplan could be intimidated, that by insulting her or playing his usual domination tricks, she would falter. Obviously, he didn’t know his adversary. The New York Times described them as “two New Yorkers, both formidable combatants and talkers.”

The good news is that only one of them is terrific at what she does.