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.”

Robbie has consistently been ranked by Chambers and others as one of the top litigators in the country.  Chambers (which ranks Robbie as Band 1 in three separate categories: commercial, employment litigation and higher education) has called Robbie “a modern-day legal giant. A towering intellect and a genius in court, with the instincts of a street fighter.” In 2025, anonymous reporters on Chambers described Robbie as a “force of nature” who is very good at submitting “drop-the-mic” briefs for her clients.

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.

Commercial Litigation

Robbie made partner at Paul, Weiss a year early (in 1998) based on her work for Sumitomo Corporation after one of its copper traders confessed to years of rogue trading in 1996, resulting in a loss of more than $2 billion dollars. Robbie, as the senior associate on the case, first led a large team investigating the facts on the ground in Tokyo and then turned to defending Sumitomo in multi-jurisdictional regulatory investigations, civil litigation, and then prosecuting actions against those who assisted the rogue trader.

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

Robbie, for example, recently won a stay in favor of arbitration in connection with litigation Sean Combs brought against the international liquor company Diageo relating to certain vodka and tequila brands, which ultimately led to a favorable settlement. She also represented Authentic Brands Group in its dispute with the former operator of Sports Illustrated, which also resulted in a favorable settlement. Robbie currently represents Diageo in a series of multi-jurisdictional class actions challenging the labeling of Casamigos and Don Julio tequilas.

Robbie has handled a wide variety of cases representing clients in the financial services sector, including matters involving SPACs, stock analyst recommendations, market timing in mutual funds, reinsurance transactions, structured finance transactions and multi-level marketing companies.  She represented Citigroup in class actions resulting from the collapse of Worldcom in 2002 and the insurer AIG in a series of regulatory and litigation matters relating to the restatement of its financials.

In the wake of the financial crisis in 2007, Robbie represented Fitch Ratings in dozens of regulatory investigations and civil litigations in both state and federal court relating to Fitch’s credit ratings of RMBS, CDO, and municipal bond transactions. She represented JP Morgan and a syndicate of other banks in a bankruptcy adversary proceeding relating to the collapse of the housing market.  More recently, she represented Pershing Square in a case defending the legitimacy of SPACs under the Investment Company Act.

Robbie has also been honored to represent major law firms in connection with their insurance, commercial, employment, and related matters.

Higher Education

Robbie has earned a reputation for helping top universities navigate their most pressing challenges. She has represented Columbia University for over a decade in cases related to allegations of gender-based misconduct, helping to shape the contours of the Title IX jurisprudence in the Second Circuit.  See, e.g., Nungesser v. Columbia Univ., 169 F. Supp. 3d 353 (S.D.N.Y. 2016); Roskin-Frazee v. Columbia Univ., 474 F. Supp. 3d 618 (S.D.N.Y. 2019). Robbie also secured the dismissal of breach of contract claims in lawsuits against Columbia seeking hundreds of millions of dollars in tuition refunds related to the restrictions imposed on campus during the COVID-19 pandemic. In re Columbia Tuition Refund Action, 20 Civ. 3208, 2021 WL 790638 (S.D.N.Y. Feb. 26, 2021).

Robbie currently represents Columbia in Title VI matters arising out of events on campus since the horrific terrorist acts by Hamas in southern Israel on October 7, 2023. With respect to the recent wave of partisan attacks on “affirmative action” or “DEI,” Robbie secured a dismissal of a case brought by a student challenging NYU Law Review’s selection process in light of the Supreme Court’s decision in Students for Fair Admissions. Doe v. N.Y. Univ., No. 23 Civ. 10515, 2024 WL 2847368 (S.D.N.Y. May 30, 2024).

In the area of Title IX and college sports, Robbie defeated a motion for a preliminary injunction seeking to require Brown University to restore its squash teams to varsity status. Sterman v. Brown Univ., 513 F. Supp. 3d 243 (D.R.I. 2021). She similarly succeeded in negotiating an end to a decades-old consent decree that required Brown to maintain exceedingly narrow gender proportionality requirements with respect to its athletics teams. Cohen v. Brown Univ., 16 F.4th 935 (1st Cir. 2021).

At the height of the COVID pandemic, Robbie conducted a groundbreaking investigation into gender equity issues arising out of the 2021 NCAA Division 1 women’s basketball championships. In that report, Robbie predicted the stunning rise in the popularity of women’s basketball, concluding that the NCAA had significantly underestimated the value of the women’s game. The vast majority of the recommendations in Robbie’s report have been adopted by the NCAA.  

Government Matters

Throughout her career, Robbie has been involved in cases defending or challenging a wide variety of federal, state and local government laws and regulations.

Robbie’s very first trial where she acted as “first chair” or lead trial lawyer was the dispute between PG&E and Robbie’s client, the California Public Utilities Commission (CPUC) resulting from the 2001 California energy crisis.  In that case, PG&E sought to avoid regulation by the CPUC going forward as part of its bankruptcy plan. Although the case settled mid trial, PG&E failed in its effort to evade state regulation.

Robbie has also succeeded in quashing a NYAG subpoena and then obtaining a preliminary injunction for Airbnb on Fourth Amendment grounds, blocking a New York City ordinance that would have required Airbnb to turn over virtually all of its business records. Airbnb, Inc. v. Schneiderman, 989 N.Y.S2d 786, 788 (Sup. Ct. 2014); Airbnb, Inc. v. City of New York, 373 F. Supp. 3d 467 (S.D.N.Y. 2019). She has also represented Uber in several cases involving regulations that posed similar business and privacy concerns. Robbie is currently representing a leading affordable housing developer in contract-related disputes.

Most prominently, Robbie 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 to prevent the Trump Administration from terminating federal approval for congestion pricing and seeking to force compliance by withdrawing funding and approvals.

Robbie is currently ranked as one of the 50 most powerful lawyers in New York by City and State.

Employment, Discrimination & Gender-Based Misconduct Matters

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.  Carroll v. Trump, 124 F.4th 140 (2d Cir. 2024). The second verdict, which involves issues of waiver under the Westfall Act and principles of presidential immunity, is still on appeal.

Robbie has also represented a woman sued by a prominent Hollywood producer for defamation after she posted on Facebook that he had sexually assaulted her years earlier, as well as the parents of a boy who tragically committed suicide after he was relentlessly bullied at a boarding school. She has also obtained many multi-million-dollar confidential settlements for victims of bullying, discrimination and sexual assault, including for victims of Jeffrey Epstein.

Public Interest Matters

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.”

Robbie 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, 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. In November 2021, after a four-week jury 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.

In 2024, Robbie 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 Robbie 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.

Recognition and Publications

Among numerous honors and recognitions, Robbie was recognized as the 2020 “Attorney of the Year” by the New York Law Journal, received a Lifetime Achievement Award from the New York Law Journal, and has been honored as “Litigator of the Year” by The American Lawyer, “Lawyer of the Year” by Above the Law, and “Most Innovative Lawyer of the Year” by The Financial Times. The Financial Times noted at the time that “the judges had little trouble picking just one of them to win the award for most innovative individual – itself an innovation for the report this year. Robbie Kaplan has been involved in some of the most important legal developments of recent years.”

Robbie is the author of the book Then Comes Marriage: United States v. Windsor and the Defeat of DOMA (W.W. Norton), chosen by the L.A. Times as one of the top ten books of 2015 and praised by President Bill Clinton as “a riveting account of a watershed moment in our history, and the strategy, ingenuity, and humanity that made it happen.”

Robbie holds a J.D. from Columbia Law School in 1991, where she teaches a seminar on Advanced Civil Procedure. She earned her A.B., magna cum laude and phi beta kappa, from Harvard College in Russian History and Literature in 1988.