Roberta Kaplan

Practice Areas

Appellate Litigation; Commercial Litigation; Education; Employment, Discrimination and Sexual Misconduct; Investigations and Crisis Management; Public Interest Litigation; Regulatory Enforcement and Litigation; Trials

Career

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 Robbie 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.”

Robbie is known both for her intellectual creativity and her dogged determination. The head of litigation at Sullivan & Cromwell is quoted in a profile of Robbie explaining that Robbie “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.”

On behalf of her client, E. Jean Carroll, Robbie 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.

Clients

Robbie’s career has focused on representing clients across a wide array of industries and fields (including technology, entertainment, higher education, consumer products, and financial services) in their most complex regulatory and litigation challenges.

Work Highlights

As noted above, Robbie has represented E. Jean Carroll since 2019 in two cases alleging defamation and battery arising out of Donald Trump’s sexual assault of Carroll in a Manhattan department store dressing room in 1996. Both cases went to trial and Robbie recovered a total of more than $88 million from two separate juries in the Southern District of New York. The first verdict has been affirmed in a 77-page per curium opinion by the Second Circuit. The second verdict, which involves issues of waiver under the Westfall Act and the doctrine of presidential immunity, is still on appeal.

Robbie also serves as counsel for the Metropolitan Transit Authority (MTA) in connection with at least twelve separate lawsuits seeking to block the implementation of congestion pricing in New York City, all of which have failed, paving the way for congestion pricing to begin in January 2025. As a result of Robbie’s efforts, Janno Lieber, Chair and Chief Executive of the MTA, observed: “We’ve been sued in every federal court and state court east of the Mississippi, and we’re batting 1,000.” Robbie currently represents the MTA in a lawsuit that the MTA filed where she has prevented the Trump Administration from terminating federal approval for congestion pricing and seeking to force withdraw funding and approvals for transportation projects in New York.

In addition, Robbie 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.”

In 2017, Robbie 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. After a four-week trial, Robbie 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 Robbie’s work on the Charlottesville case.

Education

Awards