To many, Armonk resident David Boies’ soft-spoken, aristocratic demeanor belies a cunning, even ruthless, legal mind within.
David Boies settles into a moss-green club chair inside his elegant home office. The room is cozy, lined with books and dotted with family photos, with a picture window overlooking the manicured rolling hills of his Armonk estate. Boies, wearing his signature Lands’ End navy-blue suit with a blue-checked shirt, begins by saying, “Let me just show you one thing.”
He hands over his iPad, which displays a photo of a smiling Boies standing behind a huge African tortoise.
“Isn’t that great?” he asks.
The tortoise is magnificent and looks as if it weighs at least 150 lbs. But what is Boies really saying by opening an interview with this image? That he will only be revealing his polished exterior? That a tough façade protects a more vulnerable inner self? That slow and steady wins the race — particularly when it comes to his storied legal career? That he’s a survivor? Or maybe that he and his wife, Mary, simply enjoyed a recent safari in Kenya.
One thing is certain: David Boies is in control. Yet despite his high profile as one of the most famous lawyers in the country, the inner Boies remains something of a mystery.
The 78-year-old legal legend — who has argued in front of the Supreme Court seven times — has been variously described by colleagues and journalists as “the Michael Jordan of the courtroom,” “the Tiger Woods of the legal world,” and “the greatest trial lawyer alive.”
Listing his awards would take pages, but they include “Global Litigator of the Year” by Who’s Who Legal (seven times), “Litigator of the Year” by The American Lawyer, and “Lawyer of the Year” by the National Law Journal. Even TIME anointed Boies one of the “100 Most Influential People in the World,” to say nothing of the recognition he’s received for his work in social justice.
Socially, Boies is warm and charming. Professionally, he can be ruthless and intimidating. The New Yorker depicted a Boies cross-examination as “a little like watching your cat play with his food before he eats it.” In one high-profile case, reporters started humming the theme song from Jaws each time Boies approached an opposing witness. Sometimes, after undergoing a pretrial Boies deposition, witnesses for opposing counsel decide not to testify.
“Winning is not that hard; you have to want it enough. He once asked a colleague, “Do you want to win, or do you want to sleep”.”
“He’s almost like a snake charmer,” says Theodore B. Olson, himself a famous attorney who has worked with Boies as both co-counsel and opposing counsel. “He focuses on the witness, and the witness is almost hypnotized. David will lead him or her down a path, using the witness’s own words or reasons and then puts them in a logical chain that leads them to a conclusion that was the opposite of what they wanted to say.”
David Boies’ legal prowess is clear, but other aspects of his life are less so.
He looks to-the-manor-born, with a patrician appearance, a vague resemblance to the Bush family (my editor, who has met Boies, says, “Lincolnesque”) and a lifestyle that includes a 17-acre property in Westchester, a 900-acre California winery, and a 184-foot sailboat. But Boies’ upbringing in Illinois was modest. His father, a high school teacher, worked several other jobs to support the family of five children. Boies himself started working at age 10 (a paper route) and worked his way through college and law school. He learned to fight when his family moved to Compton, CA, when Boies was in seventh grade. He’s so articulate that he speaks in fully formed paragraphs, yet he suffers from dyslexia and didn’t read until the third grade.
Until a few years ago, Boies was a darling of those who lean left politically. A Democrat, Boies, with co-counsel Olson (a conservative Republican), successfully argued in favor of same-sex marriage in front of the Supreme Court. To this day, Hollingsworth v. Perry remains the case Boies is most proud of, because “it is the case that’s impacted the most lives positively.” He represented Al Gore in the 2000 presidential election recount — a rare defeat. (Olson, his opponent in that case, led the winning team.)
Back in the 1980s, David Boies successfully represented CBS in a libel case brought by General William Westmoreland. CBS had run a documentary accusing the general of underestimating enemy troop strength in Vietnam. Boies undermined Westmoreland’s credibility, pointing out contradictions in his testimony. In another high-profile case, Boies won the government’s antitrust suit against Microsoft, where he reportedly reduced Bill Gates to a stammering, sullen witness.
David and Mary Boies preside over their majestic 17-acre estate in Armonk, where they often socialize with friends Tom and Meredith Brokaw.
The last few years have been less kind to Boies’ legacy, however. Starting in 2017, headlines popped up about Boies’ “fall from grace.” In September 2018, a New York Times profile ran the headline “Boies Pleads Not Guilty.” The representation of two different clients — Harvey Weinstein and Elizabeth Holmes — made Boies a lightning rod for criticism by some of the same people who’d once lauded him. He’d represented Weinstein prior to the sexual assault accusations but kept him as a client after the scandal broke, eventually dropping him in November 2017. “I’m loyal,” Boies says.
Moreover, Boies’ firm, Boies Schiller Flexner, hired investigators to dig into the personal lives of Weinstein’s accusers (which Boies would later admit was a mistake on his part). Boies also came under fire for representing Holmes and her disgraced startup, Theranos. The company’s claims of running extensive blood tests from one drop of blood proved to be fraudulent. Boies was not only Holmes’ lawyer but also on the board of her company, which critics claimed was a conflict of interest. Further, Boies’ firm was accused of intimidating whistle-blowers and journalists who tried to divulge the company’s failures.
To be a great litigator, Boies says, one must have the ability to create a compelling narrative that can stand up to cross-examination. And Boies does exactly that when asked to explain the seeming contradictions and controversies in his legal career.
“A lot of people misunderstand what lawyers do,” Boies says. “I think it’s misguided and even dangerous to undercut the indivisible protections we’ve built up over the centuries — protections like the presumption of innocence, the right to counsel, the right to trial by jury. You can’t only give those protections to people you like. These are fundamental to a democratic society, fundamental to a progressive society.”
Boies says he doesn’t mind the personal hits he has taken, noting he hasn’t lost any clients. But he’s particularly upset about the case of Ronald S. Sullivan Jr., a law professor at Harvard Law school, and Sullivan’s wife, Stephanie Robinson. The two were the first African American faculty deans in Harvard’s history. When Sullivan joined Harvey Weinstein’s defense team, some students protested, and Harvard chose not to renew the couple’s contracts, according to multiple news reports. Sullivan ultimately withdrew from the case, and according to the Harvard Law School website, at press time, the two remain on staff.
Boies calls the dismissal a dangerous precedent, arguing that institutions of power shouldn’t be penalizing lawyers who take on cases that others find objectionable. “When people, whether they are conservatives or progressives, undercut those principles because they disagree with a particular way they are being applied or because they find a particular person reprehensible, it endangers those principles for everyone.” And, he warns, it’s generally the most powerless and vulnerable people who most need those rights protected.
“I’m much more excited by a good lawsuit than playing bridge or poker…”
The attorney’s work ethic is legendary. Boies believes that “winning is not that hard; you have to want it enough.” He once asked a colleague, “Do you want to win, or do you want to sleep?” Boies believes he was likely in the bottom half of his Yale Law School class intellectually but graduated at the top through hard work. His dyslexia taught him valuable legal skills, including patience, skillful oral communication and careful listening, he says. Boies never uses notes in front of a jury — he can’t process the written words quickly enough — so he’s learned to be in command of all the facts.
“A trial is more about the molding and presentation of a narrative than it is an exposition of the finer points of law,” says Boies.
Deeply competitive, Boies’ confidence is well-earned. In 2009, when he and Olson filed the lawsuit to overturn California’s ban on gay marriage, the two were intensely criticized from both the left and the right. Conservatives attacked Boies and Olson for undermining public morals. Liberal groups, including the ACLU and Lambda (an organization dedicated to achieving civil rights for LBGT people) warned them it was too early to bring the case and that a defeat would be a huge setback for equality. They advised waiting for a more liberal Supreme Court. But Boies believed they could win, and they did. (“Can you imagine if we’d waited?” he asks now.) He keeps in touch with the plaintiffs and celebrates their wedding anniversaries.
Boies Schiller Flexner devoted more than $12 million worth of time and expenses on the suit, Boies says. “We decided early on that we were going to take on the cases that required a level of resources that very few firms were able to devote, the kind that require investment of literally millions of dollars, [because] those firms that were able to devote it, largely didn’t.”
Other large pro bono cases by Boies’ firm include a successful suit against the state of Florida for failing to provide medical treatment under Medicaid to poor children. Boies was also instrumental in a pro bono suit to shut down Backpage, a sex-trafficking website. His current high-profile work is on behalf of the victims of the late Jeffrey Epstein, an alleged financier accused of conducting an international sex trafficking operation involving hundreds of underage girls. The Epstein case triggered a clash of legal titans when Boies Schiller Flexner client Virginia Roberts Giuffre accused Harvard law professor and former OJ Simpson attorney Alan Dershowitz in 2014 of having sex with an underage Giuffre as part of Epstein’s sex-trafficking network. (Boies has since taken on additional alleged victims pro bono.) Dershowitz responded with multiple bar complaints against Boies and his firm for unethical conduct (all of which have been dismissed, says Boies) along with a war of words in the media.
Yet Boies revels in his family at least as much as he does in contentious legal battles. With surpassing pride, he lists some of the many accomplishments of his wife, Mary, a towering legal figure in her own right. They include stints as a VP at CBS, general counsel of the U.S. Aeronautics Board, assistant director of the White House Domestic Policy staff under Jimmy Carter, and counsel to the U.S. Senate Commerce Committee. She sits on multiple boards and is currently vice chair of Business Executives for National Security, as well as a board member of the Council on Foreign Relations. Not surprisingly, the Boieses often seek advice from each other for whatever happens to be pending on their respective legal dockets.
Mary, her husband claims, is even more driven and disciplined than he is — and not just in her career. The no-nonsense 69-year-old brunette is a highly competitive athlete, boasting top finishes in multiple triathlon events for her age group. Sometimes, when the two go out for dinner, David will drive, and Mary will ride her bike to meet him. On vacations to Virgin Gorda, in the British Virgin Islands, Mary paddleboards more than 13 nautical miles, to the island of Tortola.
“She sometimes makes me exhausted just watching her,” Boies admits.
Two side-by-side photos just outside Boies’ office tell the story. In one, taken from high above, David is sunbathing languidly on the deck of a sailboat they’d owned. The other photo shows Mary, who has scaled the mast to, yes, photograph her husband.
Boies had six children: two with his first wife (his high school sweetheart), a set of twins with his second wife (whom he met at law school), and two with Mary. However, he has lost two adult children. His daughter Caryl died of lung cancer in 2010 at the age of 48, and last spring, his son Jonathan died of a rare vascular brain condition at age 50. Most of Boies’ surviving children and 11 grandchildren live nearby.
All of his children except for one daughter went to law school. In addition to intergenerational family barbecues and picnics, there are — not surprisingly — competitive family games. Boies admits to being sore from a crash during a recent family badminton game, where he and his son Christopher took on son Alex and his girlfriend. (Boies manages to mention that his team won.)
Like most, David Boies treatures family and leisure time, though the 78-year-old is by no means finished with his career. After all, he says, “There’s still a lot of justice to be done.”
The Boieses also love their county of residence, Westchester, for both its countryside and easy access to Manhattan. They’re loyal patrons of Le Crémaillère in Bedford but also like Amore in Armonk for casual fare. Good friends Tom and Meredith Brokaw live nearby; the two couples socialize often, including traveling together.
David Boies is a generous friend, says Olson. “He’s an extraordinarily kind person, despite being a competitive person, and he’s very competitive. Despite how busy he is, and he’s very busy, David is very thoughtful, always reaching out. If anyone he knows is in trouble or needs help, David is the first one to lend a hand.”
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That generosity extends to his community. Boies has to be pushed to talk about the family’s local philanthropy but acknowledges their support of Bedford Presbyterian Church, Northern Westchester Hospital, and Westchester Community College. (He does not mention that he and Mary donated $5 million to the hospital or that the emergency department is named for them.)
David Boies’ Westchester wine cellar, meanwhile, is legendary, housing in excess of 10,000 bottles at a crisp 53.9 degrees. His California winery, Hawk and Horse, produces a red Cabernet Sauvignon and a red dessert wine. When Boies descends to the basement of his house to show off his collection, it feels as if he is proudly revealing secret treasure. He cradles double magnums of 1982 Lafite Rothschild and 1982 Chateau Latour. The shelves are meticulously ordered, yet on the floor, stacks of unopened wine cases are everywhere.
Speaking of cases, you’d think most litigators at this stage of their career would take a victory lap, uncork one of those amazing bottles, and relax. But not Boies, for whom retirement holds no interest. “I’m much more excited by a good lawsuit than by playing bridge or poker,” he says. “I’d much rather spend 80 percent of my time practicing law and 20 percent playing cards.”
David Boies walks out of the wine cellar and down the hallway, which is lined with magazine covers highlighting his career, awards, family photos, and the drawings of grandchildren, pausing just long enough to adjust a framed photo of son Jonathan. As he heads back upstairs for his next appointment, Boies does not look like a man ready to hang up his briefcase. With a small smile, he notes, “There’s still a lot of justice to be done.”
For 20 years, Kate Stone Lombardi was a regular contributor to The New York Times, eight of them as a columnist for the Westchester section. Kate’s work has also appeared in the Wall Street Journal, Ladies Home Journal, Good Housekeeping, and TIME. She is also the author of THE MAMA’S BOY MYTH (Avery/Penguin, 2012).
