The Fearless Robbie Kaplan
1Digest
Roberta Kaplan, a distinguished civil litigator known for suing Donald Trump twice, shares insights into her career, from her early life in Moscow to her path in law. She reflects on the challenges women faced in the legal profession and emphasizes the power of litigation to drive societal change, citing marriage equality as an example. Kaplan details her strategic approach to case selection, witness assessment, and her notable work on the E. Jean Carroll case against Trump, including her "spider strategy" during depositions. She also touches upon the financial aspects of contingency cases, the influence of political power on the legal system, and her analysis of the #MeToo and Times Up movements. The discussion extends to media scrutiny, her transition to starting her own firm, observations on law students, and humorous anecdotes. Kaplan further explores civil procedure reform, jury dynamics, settlement strategies, judicial decorum, and the art of legal persuasion. She recounts her experiences building her own firm, the importance of understanding judges, and shares personal stories about her wife's activism and her own early career aspirations. Finally, she discusses her current case against Elon Musk and expresses concerns about campaign finance and the Supreme Court.
Outlines
Introduction and Early Life Influences
Introduction of Roberta Kaplan, a renowned civil litigator. Kaplan shares her formative experience living in Moscow in 1987 during Glasnost, describing the totalitarian regime and its impact on her worldview, and discusses her non-legal family background and her decision to pursue law.
Navigating the Legal Profession and Driving Change
Kaplan reflects on the challenges for women in law school and early career, highlighting subtle biases. She emphasizes the significant impact lawyers can have on society through litigation, using marriage equality as a prime example.
Strategic Litigation: Case Selection and High-Profile Cases
Kaplan outlines her approach to selecting cases, focusing on witness credibility and evidence. She details her strategy in the E. Jean Carroll case against Trump, discussing witness strengths and the unique aspects of the accusation, and explains her "spider strategy" used in depositions.
Financial Realities, Political Influence, and Social Movements
Kaplan discusses the financial risks of contingency cases and how external funding secured the E. Jean Carroll case. She speculates on political influence affecting legal outcomes and analyzes the successes and failures of the #MeToo and Times Up movements.
Career Transitions, Teaching, and Personal Anecdotes
Kaplan recounts facing media scrutiny, her departure from a large firm to start her own, and her experiences teaching law students. She shares a humorous story involving her son and Justice Ruth Bader Ginsburg at the White House.
Civil Procedure, Trials, and Judicial Matters
Kaplan discusses civil procedure reform, the role of judges, and jury dynamics, including challenges during COVID-19. She clarifies the nature of the verdict against Trump and emphasizes the importance of judicial decorum and support for legal professionals dealing with trauma. She also touches on legal persuasion and the interpretation of evidence like text messages.
Building a Firm, Understanding Judges, and Personal Background
Kaplan details establishing her own law firm to achieve case diversity and stresses the critical importance of understanding a judge's approach. She shares an anecdote about a prosecutor internship application and describes her wife's political activism.
Political Landscape, Current Cases, and Legal System Concerns
Kaplan reflects on the political climate, expresses hope for future repair, and discusses her current case against Elon Musk. She advocates for campaign finance reform and voices concerns about the Supreme Court's impact on faith in the legal system.
Keywords
Civil Litigator
A lawyer specializing in civil lawsuits, handling disputes between individuals or organizations, aiming for resolution through negotiation, settlement, or trial.
Totalitarian Regime
A form of government that theoretically permits no rival power or opposition, characterized by extreme control over public and private life.
Glasnost
A Soviet policy of open discussion of political and social issues, introduced by Mikhail Gorbachev in 1985, aiming for greater transparency.
LGBTQ+ Rights
Legal and social equality for lesbian, gay, bisexual, transgender, and queer individuals, including marriage equality and protection against discrimination.
Donald Trump
45th President of the United States, known for his business career, political campaigns, and numerous legal challenges.
E. Jean Carroll
A writer and columnist who successfully sued Donald Trump for defamation and sexual abuse, winning significant jury verdicts.
Deposition
Out-of-court testimony given under oath, typically in response to written or oral questions, used as evidence in civil litigation.
Contingency Fee
A fee arrangement where a lawyer's payment is dependent on winning the case, usually a percentage of the recovered damages.
#MeToo Movement
A social movement against sexual abuse and sexual harassment, encouraging victims to share their experiences.
Campaign Finance Reform
Legislation aimed at controlling the influence of money in politics, including limits on contributions and spending in elections.
Q&A
What was Roberta Kaplan's experience living in Moscow in 1987 like?
Kaplan described living in a totalitarian regime under Glasnost, witnessing the pervasive control and the normalization of surveillance, which significantly shaped her worldview.
What challenges did women lawyers face when Kaplan began her career?
Women were scarce in law firms, lacked role models, and often encountered subtle biases, where assertive behavior considered acceptable in men was labeled negatively in women.
How did Kaplan approach the E. Jean Carroll case against Donald Trump?
Kaplan used a "spider strategy," initially appearing less confrontational, and focused on Carroll's credibility, the unique details of her story, and Trump's deposition testimony.
What is the "spider strategy" Kaplan mentioned?
It involves acting less knowledgeable initially to disarm opponents, then pouncing with strategic questions or arguments, often towards the end of a deposition or trial.
What are Kaplan's thoughts on the #MeToo and Times Up movements?
She believes they achieved overdue justice but also entered a "Robespierre period" of excessive judgment, potentially harming their long-term effectiveness and even aiding Trump's reelection.
Why did Kaplan leave a successful partnership at Paul Weiss to start her own firm?
She sought greater diversity in the size and type of cases, as the large firm's focus shifted exclusively to massive, multi-partner litigation.
What is Kaplan's current case involving Elon Musk?
She represents Imran Ahmed of the Center for Countering Digital Hate, suing Elon Musk for allegedly using his influence to have Ahmed's green card revoked due to his criticism of tech companies.
What are Kaplan's concerns regarding the Supreme Court?
She is worried about the court's willingness to overturn established precedent, like Roe v. Wade, which she believes erodes public faith in the legal system.
What advice did Kaplan's professor give her regarding a question about marijuana use on a prosecutor application?
The professor advised her to answer "experimentally," but Kaplan's honest and specific answers led to her application being withdrawn.
What is Kaplan's view on campaign finance reform?
She considers it the "lynchpin" of many national problems, arguing that without reform, particularly overturning Citizens United, the country cannot get back on the right path.
Show Notes
Roberta “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…but is perhaps best known for her recent triumph defending her client E. Jean Carroll against Donald Trump. In both 2023 and 2024, Kaplan took on Trump in court and won both cases, securing two unanimous jury verdicts against him. Kaplan has been described as the kind of “lawyer that you don’t want to see opposing you” and has been consistently ranked as one of the top litigators in the country. Kaplan also famously argued before the Supreme Court of the United States on behalf of LGBT rights activist Edith Windsor in United States v. Windsor - which resulted in a landmark decision that invalidated a section of the 1996 Defense of Marriage Act and required the federal government to recognize same-sex marriages. Kaplan was formerly a partner at Paul, Weiss, Rifkind, Wharton & Garrison before starting her own firm in 2017. In 2018, she co-founded the Time's Up Legal Defense Fund. Kaplan recently started a new firm in 2024 and is currently a partner at her firm Kaplan Martin LLP.
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