Roberta A. (“Robbie”) Kaplan is a renowned civil litigator and trial lawyer with decades of experience in commercial, higher education, government regulation, civil rights, and employment litigation. Stephen Gillers has remarked that Kaplan is the kind of “lawyer that you don’t want to see opposing you.” She has been described as “a brash and original strategist, with neither a gift for patience nor silence, a crusader for underdogs who has won almost every legal accolade imaginable.”
Kaplan is known both for her intellectual creativity and her dogged determination. The head of litigation at Sullivan & Cromwell is quoted in a profile of Kaplan explaining that Kaplan “sees things from a thousand different angles all at once . . . she knows her law cold, she knows the Constitution cold and she’s not afraid, if she sees a problem, to go to figure out some law that’s going to allow her to fix it.”
Lawdragon Honors
On behalf of her client, E. Jean Carroll, Kaplan has the distinction of being the only lawyer to have taken the deposition of President Donald J. Trump twice, and to have obtained two separate unanimous jury verdicts against him of $5 and $83.3 million respectively, with both juries reaching a verdict in less than three hours.
Kaplan has always had a deep commitment to using the law to advance the public interest. She is perhaps best known for successfully challenging a key provision of the so-called Defense of Marriage Act on behalf of her client Edith Windsor in United States v. Windsor, 570 U.S. 744 (2013), leading to nationwide marriage equality two years later. Professor Laurence Tribe of Harvard Law School has observed that he cannot “think of any Supreme Court decision in history that has ever created so rapid and broad a lower-court groundswell in a single direction as Windsor.”
Kaplan recently secured a major victory for the non-profit Center for Countering Digital Hate (“CCDH”) in a lawsuit brought by X Corp. alleging that CCDH violated X’s terms of service by researching and criticizing the prevalence of hate speech on its platform.
In 2017, Kaplan filed a high-stakes lawsuit against twenty-four neo-Nazi and white supremacist entities and individuals responsible for organizing the racial and religious-based violence in Charlottesville, Virginia, in August 2017. In November 2021, after a four-week jury trial, Kaplan and her team secured a landmark $26 million verdict against the neo-Nazis and white supremacists that has since been affirmed on appeal. Dahlia Lithwick, in her bestselling book Lady Justice (Penguin, 2022), devotes a chapter to Kaplan’s work on the Charlottesville case.
In 2024, Kaplan reached a historic settlement agreement with the State of Florida that effectively nullified the most troubling aspects of Florida’s “Don’t Say Gay” law. The settlement Robbie negotiated makes it clear that the law does not restrict references to a gay or transgender person or to a same-sex couple in public school classrooms.
Two of the public interest cases that Kaplan brought to fruition have become the subject of feature documentaries: “To A More Perfect Union” about United States v. Windsor and “No Accident” about the case against the white nationalists responsible for the violence in Charlottesville.
