Jackie Molloy for The Washington Post
On the other side of Donald Trump’s turbulent presidency, the lawyers are waiting.
Leaving aside his Senate impeachment trial, mounting government investigations include a civil probe by New York Attorney General Letitia James, a criminal probe by Manhattan District Attorney Cyrus Vance Jr., and a federal probe by acting U.S. Attorney for D.C. Michael Sherwin that may include Trump’s role in the catastrophic storming of the U.S. Capitol this month.
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.”
Before the presidency, Trump was often as engaged in legal tussles as he was in real estate, suing and threatening to sue his way out of financial trouble. With a return to private life, “his terror is that he will no longer be protected by the office and will have to deal with these lawsuits,” says his niece. Trump faces the prospect of spending considerable time in the role of defendant. Kaplan says she will seek to depose him in all three cases. Trump’s lawyers did not respond to requests for comment on the cases in this story.
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 work day.
“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.”
Stanford University law professor Pamela Karlan says of their frequent legal conversations: “Robbie’s not calling about feelings. She wants to fix it first. She’s the least diffident person I’ve ever met. Plenty of smart people worry about failing. They worry about every little thing. Robbie doesn’t worry about that. In a really disarming way, she doesn’t care if people view her as hyperaggressive.”
Kaplan speaks after arguing the Edie Windsor case before the U.S. Supreme Court in March 2013. The court ruled in favor of Windsor, seen in a pink scarf, and struck down the Defense of Marriage Act.
In Kaplan’s third Trump case, she represents participants in ACN, a multilevel marketing company promoted on “The Celebrity Apprentice.” They’re suing not ACN, but the former host and his three oldest children, accusing them of endorsing the company as a promising business opportunity.
While Trump billed himself as a populist, Kaplan perceived a consistent disconnect in how Trump University and other enterprises allegedly took advantage of the very people whose interests he claimed to champion.
“Because of his prominence, he marketed his ability to convince unsophisticated, very poor Americans to invest,” says Kaplan, who was indignant that Trump “would exploit people like this to line your own pockets.”
(In a Business Insider story, a Trump organization spokesperson responded to the suit by saying, “Before enrolling with ACN, every participant acknowledged in writing that they are ‘not guaranteed any income.’ ” In that story, ACN co-founder Robert Stevanovski claimed the plaintiffs were told that Trump was getting paid to endorse the company. “I think it’s politically motivated that they’re going to sue him and the family and not us,” he said.)
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.
Roberta Kaplan at her 1988 college graduation from Harvard University.
“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.
Five years ago, that plan expanded to landing a top Justice Department position in Hillary Clinton’s administration.
Instead, in the summer of 2017, Kaplan launched her own boutique firm, still a rarity among female corporate lawyers, creating an unusual model that combines lucrative commercial litigation with a progressive public-interest practice. Free from the agendas of risk-averse institutional clients, Kaplan and her colleagues became free to take on any case they believed had merit.
One week after the firm moved into its 71st-floor offices of the Empire State Building, the furniture yet to arrive, Charlottesville erupted.
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 — 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.
Rogelio V. Solis
Outside the federal courthouse in Jackson, Miss., in 2016, Kaplan addresses the media while representing the Campaign for Southern Equality and a lesbian couple who challenged state legislation prohibiting same-sex marriage.
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.”
Suing the powerful has brought repeated threats. Kaplan has an apartment in Manhattan but requested that her country home’s location, where she has spent the pandemic working, go unnamed.
Kaplan says the greatest abuse she’s received on social media has come not from neo-Nazis, white supremacists or Trump’s true believers, but from Depp’s vehement online champions.
Johnny Depp and Amber Heard attend the 2015 Venice Film Festival. Though Kaplan no longer represents Heard in a $50 million defamation lawsuit filed by Depp, the two remain close.
A hallmark of Kaplan Hecker & Fink is crafting complaints in layman’s language that pack a wallop. The Mary Trump brief is a doozy. “For Donald J. Trump, his sister Maryanne, and their late brother Robert, fraud was not just the family business — it was a way of life,” the complaint begins, before alleging three duplicitous schemes, “The Grift,” “The Devaluing” and “The Squeeze-Out.”
Says Mary Trump, “That brief is literature.”
The president’s lawyers, in an effort to have the case tossed, claimed that the complaint is “laden with conspiracy theories.”
When Carroll first met with Kaplan, the lawyer quickly understood her client’s objective. “I don’t give two flying figs about an apology,” Carroll says. “I am dying to get him in a deposition. I want him to say that I’m not a liar. I just want him to admit that he lied and that, yes, it happened.”
The last few years of Kaplan’s professional life, with her firm swelling from four to 43 elite lawyers, are inextricably intertwined with Trump. Without his election, Kaplan may not have launched her own firm as quickly or filed three lawsuits against him.
“I’m ready. I’m excited,” says Kaplan. In the Carroll case, Kaplan believes that Trump’s proclivity for false and misleading statements, with more than 30,000 of them during his White House term, according to The Post, will be tested when he is under oath. During a 2007 Trump deposition, lawyers caught him making exaggerated claims 30 times, according to a 2016 Post investigation.
“When we depose you, you’re not going to get away with that,” Kaplan says. “He had the mantle of the presidency, and that’s now gone.”
Jackie Molloy for The Washington Post
“My maternal grandmother always hated a bully,” Kaplan says. “One really good job for going after bullies is to be a lawyer.”
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.
Kaplan holds her son Jacob in 2006. The previous year, she married political activist Rachel Lavine at their “big gay Jewish wedding.”
“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.
Although known for her fresh legal arguments, Kaplan was comfortable working in a large firm. She seemed unlikely to go out on her own. In many ways, it’s the boldest professional move she’s made.
“What makes a good litigator and lawyer is being a pessimist and risk averse because you need to be looking at problems around the next corner,” says Karlan, who helped prepare Kaplan for the Supreme Court argument. “Robbie has been as successful as she is because she doesn’t appear to be that kind of thinker. She’s an optimist.”
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.”
At the Supreme Court in 2013, Kaplan walks with Edie Windsor, left, who had been ordered to pay federal inheritance tax of $363,000 following the 2009 death of Thea Spyer, her partner of more than four decades. Kaplan had consulted Spyer, a therapist, after coming out to her family in 1991.
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.
Citing logistical challenges that were better served by local counsel, Kaplan’s firm no longer represents Heard in the defamation case that is scheduled for trial in May.
Yet Kaplan continues to offer Heard legal advice on the case and other legal matters. They speak regularly, sometimes daily. “She is the bravest lawyer I have ever met. She doesn’t get intimidated or scare easily,” Heard says. “The well-behaved woman never interested me. There’s a rebellious part of Robbie. I think of her as my Jewish mother.”
Kaplan’s close friend Sharon Nelles, head of litigation at Sullivan & Cromwell, says: “If you can come at the world the way she does, you are not reined in by whether there are social constructs or boundaries. You can create your own mold. Lawyers for the most part react. Robbie acts.”
Nelles recalls a time when Kaplan called to consult on a case. “She’s yapping at me on the phone and then lets out a little screech.”
Nelles asked what was wrong. “Oh, I’m having a medical procedure,” Kaplan said. “Let me call you back when I get off the doctor’s table.”
Mary Trump hired Kaplan to sue President Trump, his sister Maryanne Trump Barry and the estate of his late brother Robert Trump “because I want justice for my daughter, and for me, and for my dad. If Donald Trump is not going to be held accountable for other things, he needs to be held accountable for this,” she says, adding: “Maybe that will start the dominoes to fall. Maybe other people will feel that they, too, have options and will come forward.” Kaplan’s firm regularly fields inquiries from potential clients who wish to sue Trump.
Carroll cannot wait for her day in court with Trump. She’s already picked out her outfit. Black. Armani.
She also views her lawsuit as symbolic, saying, “It’s for all the women in the country who have been harassed or assaulted by powerful men, and feel helpless to do anything about it.”
So Carroll’s doing something about it.
“I don’t have to be brave,” she says. “Because Robbie Kaplan is brave for me.”