November 14, 2025


Roberta Kaplan: Pioneering Creativity in the Legal Arena

In the latest edition of Above the Law's series, "The Rainmaker," we delve into the remarkable career of Roberta Kaplan, a litigator whose strategic creativity has reshaped the landscape of legal advocacy. As a co-founder of Kaplan Martin LLP, Kaplan has not only spearheaded significant legal battles but also redefined what it means to be a 'rainmaker' in the modern legal field.

Kaplan recalls her early days in the courtroom alongside mentor Marty London, noting the casual camaraderie between judges and male litigators, a dynamic she initially found daunting. The traditional rainmaker’s path, often characterized by male-dominated networking spaces and leisure activities like golf and cigars, seemed inaccessible and unappealing to Kaplan. However, her journey has been anything but traditional.

In 2013, Kaplan argued the landmark case United States v. Windsor before the Supreme Court, a pivotal moment that she describes as a career breakthrough achieved through innovative legal thinking. The case, fought on behalf of Edie Windsor, challenged the discriminatory Defense of Marriage Act (DOMA) on tax grounds—a creative legal strategy that ultimately expanded rights for LGBTQ+ Americans.

Kaplan’s approach to law extends beyond the courtroom. After her success in Windsor, she left the large firm environment to start Kaplan Martin, a boutique firm that combines high-caliber litigation with a more nimble, creative approach. Here, Kaplan and her team undertake cases that many larger firms might shy away from, including using the KKK Act of 1871 to sue white nationalists involved in the Charlottesville rally.

The firm’s innovative model includes forming a non-profit to support financially demanding pro bono work, allowing them to pursue justice without the constraints often faced by larger firms. Kaplan’s philosophy of legal practice emphasizes creativity not only in legal strategies but in operational tactics as well, ensuring that her firm remains agile and impactful.

Kaplan’s record speaks volumes about her influence and innovation. She has notably defeated high-profile figures like Donald Trump in court and represents organizations like the New York City Metropolitan Transportation Authority. Her work consistently demonstrates that courage and creativity are indispensable tools in the fight for justice.

Roberta Kaplan's story is not just about legal victories but about reimagining the role of a litigator and a leader. Her journey underscores that being a rainmaker is about much more than generating revenue—it's about making a meaningful impact on society and mentoring the next generation of lawyers to think differently about their roles and opportunities.

As the legal landscape continues to evolve, Kaplan’s trajectory offers inspiration and a blueprint for future lawyers who aspire to make a difference, proving that with creativity and determination, even the most entrenched systems can be challenged and changed.