Roberta Kaplan is a good example of what makes Jewish activism so effective: smart, well-connected, hyper-aggressive, in the context of a court system sympathetic to her causes. She is suing the Charlottesville protesters and was behind the successful gay marriage lawsuit; she is also E. Jean Carroll’s lawyer in her sexual assault lawsuit against Donald Trump.
Attorney Roberta Kaplan is about to make Trump’s life extremely difficultJan. 18, 2021 at 3:00 a.m. PST
But already pending for the soon-to-be South Florida retiree is a trio of lawsuits that allege defamation, fraud and more fraud — all of which are helmed by one attorney.
Roberta Kaplan’s clients include writer E. Jean Carroll, who filed a defamation case after Trump claimed she was “totally lying” about her allegation that he raped her a quarter-century ago in a Bergdorf Goodman dressing room, and niece Mary L. Trump, who claims that Trump and two of his siblings deprived her of an inheritance worth millions.
“I became the go-to person to sue the president,” says Kaplan, 54, with considerable relish.
She is in many ways the ideal legal adversary to take on Trump. Kaplan is 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. Kaplan, says New York Democratic Gov. Andrew M. Cuomo in an email, “has been indispensable in the fight against the cancer of hate and division that Trump spent four years exacerbating.”
For much of her career, there was little in Kaplan’s professional bio to suggest she would become an attorney suing behemoths. Kaplan, known to all as Robbie, is a self-described “traditionalist,” in pearls, pumps and, pre-coronavirus, superior blond highlights, who long worked as a top commercial litigator at Paul, Weiss, one of the nation’s preeminent firms, where the fees tend to be if-you-have-to-ask-you-surely-can’t-afford-us.
But she became increasingly identified as an advocate for liberal causes and outside-the-box legal strategies. She is a lesbian, an observant Jew and a die-hard Democrat for whom 12 hours constitutes a light workday.
“My maternal grandmother always hated a bully,” Kaplan says during a series of phone interviews. “One really good job for going after bullies is to be a lawyer.”
Since launching her own firm four years ago, Kaplan has initiated a constellation of cases against powerful, often intimidating forces: white supremacists, major Hollywood players, the president of the United States. Legal writer Dahlia Lithwick calls her “an attorney general for the resistance.”…Kaplan remains most celebrated for the Edie Windsor case that, in 2013, successfully struck down the Defense of Marriage Act, paving the way with stunning alacrity for the legalization of same-sex marriage two years later to the day.
Among Kaplan’s strategic moves — “I don’t know where I found the chutzpah to do this” — was to help coax Bill Clinton to publish a Washington Post opinion piece renouncing his 1996 support of DOMA before she appeared before the nation’s highest court. United States v. Windsor remains the only U.S. Supreme Court case that she has ever argued.
“A little girl with a big mouth.” That’s how Kaplan’s grandmother described her, meant with affection. Growing up in Cleveland, she was a rigorous student who designed a plan. Head East to a top school (Harvard), train as a lawyer (Columbia), become a New Yorker.…Believing that Trump’s Justice Department seemed unlikely to seriously investigate and prosecute the people responsible for the violence during the “Unite the Right” rally and counterprotest — he infamously claimed there “were very fine people, on both sides” — Kaplan announced, and this was her precise language to friends and colleagues: “I want to sue Nazis.”Because, why not?
Within days, Kaplan and her team flew to Virginia. The firm adopted an outside-the-box approach and sued two dozen avowed neo-Nazis, white supremacists and associated groups, invoking the 1871 Ku Klux Klan Act to argue that they conspired for months to commit racially motivated violence, thereby making it more of a challenge for the organizers to adopt free speech as a defense. The case is scheduled for trial in October.
In the wake of Harvey Weinstein’s sexual misconduct revelations, Kaplan co-founded the Time’s Up Legal Defense Fund, which offers financial assistance for plaintiffs filing harassment cases, and she now serves as chair of the Time’s Up organization. Many women who say they have been sexually harassed or assaulted have come to her. The actress Amber Heard sought Kaplan’s representation in ex-husband Johnny Depp’s $50 million case involving a 2018 Washington Post opinion piece by Heard; he alleges she defamed him by implying that he domestically abused her. (The op-ed does not explicitly name him.) In the complaint, the actor denies any abuse took place.Heard says of Kaplan, “I’m instantly drawn to the type of individual who can look upon the Goliath and say, ‘I think I can take you.’ That kind of energy and temerity is rare in the world, especially in the legal world.”
Kaplan is celebrated for her candor. She’s active in LGBTQ causes, recently serving as the board chair of the Gay Men’s Health Crisis. She rhapsodizes about her “big gay Jewish wedding” in 2005 to Rachel Lavine, a liberal activist who serves on New York’s Democratic committee.
Yet Kaplan remained in the closet until law school graduation.
“Robbie is one of the most conventional radicals you’ll ever meet,” Lithwick says.
In 1991, Kaplan came out to her parents at age 25. It did not go well. Her mother walked up to a wall and began banging her head, repeatedly, in dismay. “Which she has apologized for over and over again,” Kaplan says. The family remains close.
Kaplan experienced a rare episode of depression, which led her to consult a therapist named Thea Spyer, who referenced her lesbian relationship in an effort to comfort Kaplan — and whose death in 2009 left a punitive estate-tax bill to her partner, Edie Windsor, because their marriage wasn’t legally recognized, sparking the Supreme Court case that helped define Kaplan’s career.
Why did such an outspoken person hide her true identity for so long?
“I’d never been a burn-down-the-ramparts sort of person. I believed in working in institutions,” says Kaplan. “Living a life very much on the margins didn’t appeal to me. I really wanted to have kids. I really wanted to be part of the Jewish community. I really wanted to have a career. All of this would have been unavailable in the world I grew up in.”
She has all of that — the marriage, a son (Jacob, now 14), a goldendoodle. On Sunday mornings, she participates in a Talmud discussion group with her rabbi and Lithwick.
“Also, I knew when I met Rachel there was no way I was going to be able to be in the closet and be with Rachel,” Kaplan says. “Those two things were completely incompatible.” Everyone in the New York gay rights movement knew Lavine. Politics, civic engagement and intellectual rigor were part of the attraction. On an early date in a romantic Chelsea bistro, the two argued at length over the comparative power of the Bolsheviks and the Mensheviks during the Russian Revolution.
The firm’s high-profile cases have attracted top legal talent, like Joshua Matz, who briefly left the firm last year to help the House Judiciary Committee draft articles of impeachment.
“We’ve learned that, in presenting options to Robbie, she will presumptively favor the most aggressive option,” Matz says. “She is jaw-droppingly strategic and savvy on the one hand, and extremely bold on the other.”
It’s also a menschy practice. “What’s unusual is the sheer amount of contact she has with her clients,” Karlan says. Kaplan celebrated Passover with Windsor, who died in 2017. She’s available at all hours for phone consultations. Gifts of food are constant. She sent Heard a box of chicken soup, lox and bagels.
From The Washington Post