Roberta Kaplan

Kaplan has made her mark on legal history in myriad ways. A champion of the #MeToo movement and a pioneer for LGBTQA+ rights, Kaplan co-founded the Time’s Up Legal Defense Fund in 2018, which continues to provide legal support to victims of workplace sexual harassment and discrimination.

Kaplan’s most recent headline-making wins were against former president Donald Trump, who was ordered to pay E. Jean Carroll $5 million for sexually abusing her and for later defaming her in a social media post; a second judgment for $83.3 million followed for further defamation. It’s the kind of win that requires tough-as-nails advocacy and litigation skills, which define Kaplan’s career.

“Becoming a great lawyer requires that you be courageous, press boundaries wherever you are, and insist that things can always change for the better,” Kaplan says. “A lawyer should take on a client or cause because you know in your mind and in your heart that it’s the right thing to do.”

Although Kaplan heads a successful white-collar defense and commercial litigation boutique, with clients including UberUBER -2.1%, Airbnb and presidential daughter Ashley Biden, she is also renowned for her advocacy and pro bono work. Case in point: her landmark case United States v. Windsor, which ultimately invalidated a section of the 1996 Defense of Marriage Act (DOMA) and required the federal government to recognize same-sex marriage for the first time.

Kaplan believes it’s important to ward off “corrosive cynicism” and to trust a system where cases are tried on their merits, by judges and impartial juries. One quote in particular, written by a rabbi long ago, keeps her motivated: “‘All the world’s a very narrow bridge. The main thing is not to be afraid.’ This could have been written by a lawyer today,” Kaplan says. “We must not succumb to fear or cynicism. The work we do every day to uphold justice matters.”