Roberta Kaplan knows how to beat Donald Trump in court. She's already done it twice.
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The lead attorney representing E. Jean Carroll secured a major legal victory against Trump last week in a trial that resulted in an $83 million judgment against the former president for defaming the writer. It was the second time in less than a year that Kaplan beat Trump and his legal team after Carroll went public in 2019 with her account of being sexually assaulted by Trump in a Bergdorf Goodman dressing room in Manhattan in the 1990s.
“The single most important thing that Donald Trump convicted — both from his deposition and from the trial — is Donald Trump’s own behavior,” Kaplan told me.
Long before that, however, she had earned a reputation as one of the most skilled and consequential litigators of her generation. She brought the case that resulted in United States v. Windsor, the landmark Supreme Court ruling that established federal recognition of same-sex marriage in 2013. She was also a member of the team that successfully sued the organizers of the infamous 2017 rally of white supremacists in Charlottesville, Virginia.
I first met Kaplan — “Robbie” to those who know her — well over a decade ago, while working with her when I was a young lawyer. We have remained friendly since then, as our career paths have taken us in very different directions and, more to the point, as her stature in both the legal and political worlds has grown.
I spoke with her this week about her recent trial victories of ella, her experience of ella litigating against Trump, and how federal prosecutors — who are doing their best to put Trump on trial before November — can maximize their odds of success of ella in court.