In October, a New York judge ordered that the prominent American litigator David Boies be barred from representing Virginia Roberts Giuffre, his client and one of the many victims of the now deceased financier–sex trafficker Jeffrey Epstein, in her lawsuit against Alan Dershowitz, the former Harvard law professor. Although Giuffre would have to find another attorney, the good news was that she could go forward with her defamation suit against Dershowitz, Epstein’s former lawyer, for calling her a liar—“a certified, complete, total liar”—for alleging that the 81-year-old lawyer had sex with her on multiple occasions when she was 16.

For Boies, the decision was a serious setback. The lawyer to at least three of Epstein’s victims, including Giuffre, the famous litigator had become nearly as central to the case as Epstein. They were almost twinned. The white knight to the financier’s dark prince, Boies grabbed the chance to be a fierce advocate for Epstein’s victims. He threatened on the British television show Panorama to subpoena Prince Andrew, one of the men to whom Epstein is alleged to have pimped out Giuffre and other under-age women, which the prince has repeatedly, and recently very publicly, denied. In early November, Boies went so far as to personally sue Dershowitz, a longtime foe, for defamation after he publicly suggested that Boies was trying to extort him. It was Dershowitz’s extortion allegation that triggered Boies’s removal from Giuffre’s case against Dershowitz—on the grounds that Boies was a possible witness. For the 78-year-old Boies, it seemed, the Epstein legal drama had become a crusade, a desperate effort to launder a once gleaming reputation that had been soiled.

If so, it has all gone badly awry. For just as he appeared close to achieving the redemption he sought—after two years of public opprobrium over his relationship with Harvey Weinstein, his almost blind support of Elizabeth Holmes and Theranos, his strong-arm tactics against journalists, and conflict-of-interest questions—Boies was back in the murk. In a stunning report in The New York Times this month, he was cast in a sordid and outlandish alleged scheme to use sex videotapes, purportedly belonging to Jeffrey Epstein, to coerce powerful men—including former Israeli prime minister Ehud Barak—and pressure others into paying multi-million-dollar private settlements to their victims in exchange for keeping their actions secret. Set in motion in late August, shortly after Epstein died in his jail cell, reportedly by hanging, the plan was even more astonishing, perhaps, because Boies, a lawyer renowned for his ability to read people, was said to have been taken in by a con man—claiming to be a hacker—who refused to reveal anything about his true identity, including his name.

It beggars belief that, after the public outcry over his past behavior, as he was trying to resurrect his reputation, Boies appears to have jumped even deeper into the muddy waters of questionable ethics and judgment.

In America, it is the season of fallen idols. The pedestals have been crumbling across the land, from the media establishment to the political world and beyond. Charlie Rose, Les Moonves, Al Franken, Matt Lauer, and Linda Fairstein—the former New York sex-crimes prosecutor culturally canceled this year over her 1989 prosecution of the Central Park Five—were among the many who were toppled. Boies’s was one of the steeper falls. The news stories about Boies today startle in comparison with those of the past. There is Boies, as described in The New York Times: poring over grainy photographs—allegedly stills of videos—of couples having sex, trying to identify the men. And the wince-making updates of Boies’s feud with Dershowitz: “I have had sex with one woman since the day I met Jeffrey Epstein. I challenge David Boies to say under oath that he’s only had sex with one woman,” Dershowitz railed on television to Laura Ingraham in July. Boies had the “chutzpah,” he continued, “to attack me and to challenge my perfect, perfect sex life.”

Reedy, with ice-water blue eyes, Boies for decades was, in liberal America at least, Atticus Finch and Clarence Darrow combined. The man who helped to break the Microsoft monopoly; who fought to block George W. Bush from snatching the American presidency in 2000; who battled, more successfully, for gay marriage in 2009—Boies was the man in the white hat, a cultural hero, valorized and gushed over in the press.

The first cracks in the Boies myth began to appear in the fall of 2017 with the revelations about Boies’s work for Harvey Weinstein during the years the movie producer—who is scheduled to go on trial for criminal-sexual-assault charges in January—was arranging private payments to women to bury accusations of sexual harassment and assault. The reports included Boies’s hiring of private investigators for Weinstein—ex-Mossad agents, no less—to dig up damaging information about Weinstein’s accusers and the journalists investigating him. That some of those journalists were employed by one of Boies Schiller Flexner’s own clients was perhaps even more remarkable, especially when that client, The New York Times, promptly fired the firm, calling Boies’s actions “reprehensible.”

Boies with future client Harvey Weinstein in 2002 at a book party for Rudolph Giuliani.

And there was more. In his 2018 book, Bad Blood, about fraud at Theranos, the Silicon Valley blood-testing company, the Wall Street Journal reporter John Carreyrou described threats he received from Boies and his firm during his reporting of the story, as well as their efforts to frighten and intimidate whistle-blowers, an allegation that a spokesperson for Boies’s firm, Boies Schiller Flexner, denies. Boies represented Theranos’s C.E.O., the freakily deep-voiced, unblinking, blonde Elizabeth Holmes, who is now under indictment on multiple charges, including fraud. In a tour de force of ethical acrobatics that raised eyebrows in the legal world, Boies not only represented the 35-year-old Holmes—half his fee reportedly paid for with 400,000 shares of Theranos stock—he also simultaneously sat on the company’s board, both questionable moves.

Boies has acknowledged that he made some errors—signing the contract with the Israeli investigator, for example. But he has been almost defiant in his own defense, insisting in private and in public that he was simply doing his job—representing his clients with zeal, as required by the ethics of his profession. “You don’t know all the facts when you take on a client,” he told The New York Times, “but once you do, you have a duty of loyalty.” In the case of the sex tapes, Boies did not yet have a client—because the con was discovered before any faces could be identified—but he cites as laudable and credible his goal of using the private payoffs from men to set up a fund for sex-trafficking victims, insisting that neither he nor his firm would take any money for their work. Or was this extortion? Only if the attorneys have no clients they are representing, says Stephen Gillers, professor of legal ethics at the New York University School of Law. If they have a client—which is not clear in this case, where Boies appeared to hope they had a client—it might look like a shakedown, but it’s not. At least not according to the law. “The claim of duty of zeal is what defense lawyers often assert for behavior that ordinary people would consider outrageous,” says Gillers, adding that, right now, Boies “comes across to the public as a junkyard dog.”

“I’ve talked to a lot of people, and they are all asking,” says one Boies friend, a prominent lawyer: What has happened to Boies? Is he tired? Bored? Is he getting careless? And now, with the latest revelations, is it something more serious? In today’s world, where the rules seem to have changed unexpectedly, like a river that has shifted course, exposing what has been hidden—or the tide going out and revealing “who’s been swimming naked,” in the words of Warren Buffett—some friends say Boies just found himself suddenly on dry ground. Others, however, say that, actually, very little has changed. “David has always been a person who, one way or another, has gone over lines,” says a former law partner, “sometimes way over.”

Boies tells the story himself, in his 2004 book, Courting Justice. When he was in his second year at Northwestern Law School, he had an affair with the wife of one of his professors. The school’s dean did not just ask him to leave—he sweetened the deal by offering to help get him admitted to the law school of his choice. Boies chose Yale, and the woman became his second wife in this tale that speaks to critical Boies qualities—his boldness, insouciance, disregard for rules—and to the charmed quality of his life. There was no accountability. Even better, there was no downside. He not only got the girl; he got admission to one of the best law schools in the country.

Born and raised in rural Illinois, Boies was the son of two teachers who moved to Southern California when he was 13. Dyslexic, Boies had trouble reading, but he had a near-photographic memory. Intuitive, quirkily brilliant, he excelled at the things that interested him: the debate team and playing cards for money, which would become a lifelong passion.

Boies was 18 years old when he was married for the first time, to his high-school girlfriend, with whom he had two children. To support his family, Boies took bookkeeping and construction jobs, and supplemented his income playing cards. Not markedly ambitious, he went to college at his first wife’s encouragement, graduating from the University of Redlands, outside Los Angeles. After finishing at Yale Law School in the spring of 1966, Boies went to work in New York as an associate at Cravath Swaine & Moore, then widely regarded as the best corporate law firm in the United States.

Boies’s early renown arose from two high-profile cases: his successful defense of IBM in the late 1970s in an anti-trust case brought by the U.S. government, and his defense of CBS in the 1982 libel suit brought by General William Westmoreland, the former U.S. commander in Vietnam. Boies took on some pro bono civil-rights cases, but his bread and butter—his “multi-million-dollar a year income,” as he once put it—would come chiefly from defending America’s large corporations: Continental Airlines, DuPont, Texaco, Westinghouse.

When Boies left Cravath, in 1997, his resignation was portrayed in The Wall Street Journal, The New York Times, and even USA Today as a major loss for Cravath. In the corporate world, he had become a star, which meant that he had no shortage of clients when he immediately set up his own law firm. Today the firm, Boies Schiller Flexner, has 300 lawyers in 15 offices in the U.S. and London, a far cry from its early days when Boies shared a law office with his third wife, Mary McInnis Boies, whom he married in 1982. Although Boies was joined by two top corporate litigators, Jonathan Schiller and, later, Donald Flexner, the firm orbited around Boies. At times it employed Boies’s children and wives. Over the years it attracted some marquee names to its legal staff—from 2009 to 2014, Hunter Biden, the son of Vice President Joe Biden, worked there, as did Elizabeth Wurtzel, the author of Prozac Nation; Susan Estrich, the feminist lawyer and political operative, joined the firm last year. But, except for Schiller and Flexner, says one former partner, “nobody comes close to outshining David. There are a lot of workaday, experienced litigators, but no superstars.”

Boies hated administration, preferring to focus only on practicing law, and although the firm would become more structured, it retained its homegrown style. Its finances were handled by a close friend of Boies’s, whom Boies represented in her years-long child-custody case, from her landscaping business in Palm Beach, Florida, according to New York magazine. Often, Boies’s colleagues had no idea where he was. He went frequently to Las Vegas. Gambling centered him, gave him psychic space. It was a lot like litigation, he wrote, both making it “necessary to manage your exposure while taking risks” and to be “patient and not get carried away.” Boies could be as sensitive as a racehorse. Once, he walked out in the middle of a trial, leaving his partners to carry on. “We got to court, and David made the opening statement for the plaintiffs, and then he went to the bathroom and disappeared. He never said anything; he just disappeared,” recalls one of the attorneys. “He was very secretive about where he was and what he was doing.” (A spokesperson for the firm denies the assertion that Boies ever disappeared mid-trial.)

Millions of people watched Boies filet Bill Gates on television in the fall of 1998. Even now, the video of the deposition is riveting to watch: Microsoft’s C.E.O. sitting sullenly, rocking back and forth in his chair, angry and seemingly unprepared for Boies’s relentless questioning. His photographic memory along with his view that every trial was like “a morality play” made Boies difficult to outflank. His calm, measured style, his off-the-rack suits, worn with tennis shoes, masked an intense aggression, and appealed to juries. “It is all about winning for David,” says a colleague. “The highest and best value in his value chain is to do everything you can to win for the client. It can turn into zealousness that takes him across red lines.”

The Microsoft trial made Boies a national celebrity. The admiring articles flowed, in Esquire, The New Yorker, and Vanity Fair, among many other publications. He was a runner-up for Time’s Person of the Year. The making of an American idol had begun. Boies was the David who had vanquished Goliath. Journalists, especially men, were smitten. “David is incredibly adept at the press,” says Joel Klein, who was the lead Department of Justice prosecutor on the Microsoft case. “He sees that as part of his job.” Other litigators, especially those who had seen him on rare occasions stumble badly in court, were bemused at his fame, which only grew with his representation of Al Gore in the 2000 presidential election, and his defense of gay marriage nine years later.

These were cases that Boies chose not only because of their visibility but because he cared deeply about the issues. “Both publicly and privately,” says a friend, also a lawyer, “David propounds a very ethical sense. And I think that’s part of the dilemma. The media coverage of him as a good guy and an ethical person is not inaccurate. He believes in his integrity. It’s very important to him. And yet there are all these examples of places where he appears to have breached it.”

Boies in 1985, after General William Westmoreland withdrew his $120 million libel suit against CBS. Boies represented CBS.

Boies met Harvey Weinstein around 2001. He was introduced to the movie producer by Tina Brown, then the editor of Talk magazine, which was financed by Weinstein’s company. Soon after that first meeting, Boies had a contract and a lucrative advance from Weinstein’s company to write a memoir, and Weinstein as a new client. Almost from the start, Boies was handling Weinstein’s problematic personal business. By 2002, for example, the attorney reportedly knew that Weinstein had paid settlements to women who accused him of inappropriate sexual behavior, according to Ken Auletta, who was asked by Boies not to include those payoffs in an article for The New Yorker—although a spokesperson for Boies Schiller Flexner says this allegation is false.

That same year, two women who had worked for Boies Schiller Flexner filed a sex-discrimination suit against the firm, alleging that female associates were paid less than their male counterparts, and discouraged from becoming partners, which the firm denied. Boies struck back hard, even conducting one of the plaintiff depositions himself. “It was the most scorched-earth matter I’ve ever seen,” the women’s lawyer told New York magazine’s Andrew Rice. The settlement of $37,500 per plaintiff was a coup for the firm, but a sum so meager, as Rice noted, that even the judge remarked on its paltriness. “Old Boies Club,” The Wall Street Journal headlined a 2003 story about an Equal Employment Opportunity Commission ruling that concluded there was “reasonable cause” to believe the women’s claims.

Boies has insisted that he had no idea how serious the allegations against Weinstein were⁠—at most, it appears, he thought it was the sort of harassment of women that many men in the movie business (and almost everywhere else) took almost for granted in the pre-#MeToo days. Boies says he certainly did not know there were allegations of rape or sexual assault. Even so, his relationship with Weinstein perplexed his colleagues. “Weinstein would come around occasionally and you’d have to chat him up when David was busy,” says one former partner. “You couldn’t spend 30 seconds with him and not know he was sleazy.” Some speculated that Weinstein manipulated Boies’s need to be needed. Others suggested that Weinstein hardly stood out in a firm that had come to represent some of the darker princes of power⁠—the Russian oligarch Oleg Deripaska, and Najib Razak, the former prime minister of Malaysia, who was accused of corruption. In Boies’s ethical architecture, the cornerstone was that everyone had a right to a good legal defense, no matter how rich they were. On this he was a purist⁠—to wit, his defense of Philip Morris against lawsuits by ex-smokers, even though one of his daughters had died of lung cancer.

Weinstein was also a player in what had become Boies’s circle, which included Charlie Rose, Bill Clinton, Steve Wynn, Mort Zuckerman, and Erik Prince, the billionaire C.E.O. of the global mercenary firm Blackwater. He also reportedly helped Boies’s family. The Weinstein Company cast one of Boies’s daughters in the 2012 film Silver Linings Playbook. Boies’s firm also set up Boies/Schiller Film Group, a movie-financing company run by Schiller’s son, Zack. When one of its movies, Jane Got a Gun⁠—also produced by Boies’s daughter⁠—was in financial trouble, Weinstein’s company helped rescue it with a distribution deal.

To some it seemed that the line separating Boies from his clients had blurred so much that he had become one of them. If his fortune was less substantial⁠—estimated at $20 million in 2016⁠—his lifestyle was up there. He owns a racing yacht, an estate in the wealthy enclave of Armonk, New York, an apartment in Manhattan, a vast wine collection, and a vineyard in Northern California.

In March 2016, Mary Boies flew guests to Las Vegas on chartered planes to celebrate her husband’s 75th birthday. What stood out for many of those in attendance at the lavish party was one of the people who gave honorary toasts that night: not an old friend, or a family member, but Elizabeth Holmes. Boies had met the founder of Theranos in 2011, when he was asked to represent her. As with the many prominent older men that Holmes would attract as investors and board members⁠—among them Rupert Murdoch, the head of News Corp.; the former secretary of defense Jim Mattis; and George Shultz, the former secretary of state⁠—Boies was impressed with Holmes. He later said he had no reason to doubt her claim that Theranos’s revolutionary technology could accurately test blood drawn with a pinprick. He took half his fee in Theranos stock that, at its peak, would have been worth some $7 million.

In 2015, Boies also joined Theranos’s board. While not explicitly forbidden by the American Bar Association’s ethics rules, both moves were nevertheless ethically dicey. “None of this crosses an ethical line under court rules,” says N.Y.U.’s Gillers. Some firms prohibit taking seats on clients’ boards or being paid in stock, but generally, says Gillers, “what lawyers are told is that you are in a dangerous place, this is risky, and there is a higher need for scrutiny.” By the summer of 2015, Theranos was being investigated by The Wall Street Journal’s Carreyrou, and Boies went on the attack.

Boies himself wrote a 23-page letter to the paper warning it against publishing Carreyrou’s reporting. Boies Schiller Flexner’s spokesperson denies the firm engaged in any intimidation tactics, but its reported hounding of one Theranos whistle-blower, Tyler Shultz, was described by his grandfather George, in an interview in the 2019 HBO documentary The Inventor: Out for Blood in Silicon Valley, as an “assault.” His almost compulsive pursuit of his targets⁠—like a bloodhound fixated on a scent⁠—was echoed in this fall’s sex-tape caper.

As Boies saw it, he had little choice. Such strong-arm tactics were necessary because of his obligation to defend his clients with zeal. “There is no ethical rule for lawyers that says you may not engage in outrageous behavior,” says N.Y.U.’s Gillers. “We live in a legal system that is an adversary system, and it posits that each side has an aggressive advocate and that there are only two limits on what they can do: One is court rules that prohibit certain kinds of conduct, and the other is their own sense of propriety. Some lawyers are more restrained, not because they have to be but because of who they are. Many lawyers are not restrained at all and proudly proclaim that they are prepared to go right up to the line for the client. David Boies is not alone in that attitude.”

In 2017, Boies’s firm came close to crossing that line. It sued the novelist Emma Cline for plagiarism on behalf of her ex-boyfriend, who alleged that her acclaimed novel, The Girls, contained fragments of work she had stolen from his computer. A New Yorker article revealed that firm had sent her a draft of a complaint, which contained 13 pages of sexually suggestive texts and a nude photo, that the law firm said it would file publicly if Cline didn’t settle⁠—a threat that came close to violating the rule prohibiting conduct that humiliates or embarrasses an opponent when there is no substantial purpose in doing so. The Boies firm eventually removed the photos and sexts from its complaint—but only after The New Yorker and The New York Times published the first articles about the sexual-assault and harassment allegations against Harvey Weinstein.

Ronan Farrow’s explosive New Yorker account in particular detailed the role played by Boies in the campaign to intimidate Weinstein’s accusers, including the hiring of Black Cube, the Israeli investigative firm. Boies had reportedly used the firm before, in 2017, to try to unearth dirt on Thomas Ajamie, a lawyer hired by the board of AmFAR to investigate a wildly byzantine financial deal between Weinstein and the charity. This time, however, amid the public outcry over the rape and assault allegations against Weinstein, Boies almost apologized. The “request to contract with investigators seemed at the time, like a reasonable accommodation for a longtime client,” Boies wrote in a letter to his employees. “I regret having done this. It was a mistake to contract with, and pay on behalf of a client, investigators who we did not select and did not control.” He suggested he wasn’t paying sufficient attention to what he was signing. Which could be true, according to former colleagues. “He has a very short attention span,” one says.

One can perhaps sympathize with Boies. When you can bill clients $1,850 an hour, as he does, how can you say no? How can you surprise your client by suddenly developing a conscience? The duty to zealous advocacy usually tends to become more assiduously zealous the wealthier the client. Elite lawyers have used it to weaponize the American justice system, employing the law on behalf of their corporate and wealthy clients to intimidate and harass their opponents, who often lack the means to hire their own zealous advocates.

Boies, attorney for Vice President Al Gore, meets reporters outside the U.S. Supreme Court, in Washington, D.C., having presented oral arguments in the 2000 Florida ballot-recount case.

In the incident of the con man and the sex tapes, two wealthy, successful, famous lawyers are said to have plotted to extract money from alleged sexual predators in private deals that might, one day, help some as-yet-unknown victims financially but allow the men to go free to continue their predatory behavior.

From the moment that his friend John Stanley Pottinger, the former civil-rights lawyer and author, introduced Boies to the man calling himself Patrick Kessler, Boies seemed to be hooked. And yet there were so many reasons to walk away: the photos Kessler showed them were blurry; neither the men nor the potential victims were identifiable; Boies had no idea whether any of his clients were pictured; Kessler would not tell him his real name; he wanted money. Where Kessler came from—and who, if anyone, was backing him—was a mystery. Still, Boies didn’t back off. He invited New York Times reporters to his second meeting with Kessler, ostensibly hoping that the prospect of public exposure would increase the pressure on the men to pay up, should they ever be identified. According to the Times, Boies even sought to set conditions: to maximize their leverage in settlement negotiations, he and Pottinger wanted to control which men The New York Times would write about and when.

A spokesperson for Boies Schiller Flexner says that Boies was not aware until the Times reporters told him on November 17 that Pottinger had discussed selling a videotape of a man he thought was the Israeli politician and former prime minister Ehud Barak to Sheldon Adelson, the politically connected casino billionaire. According to the Times account, however, Boies acknowledged that he and Pottinger discussed sharing with Adelson a still frame from the video on the theory that Adelson would buy it to help Barak’s election opponent, Benjamin Netanyahu. Even when the Times informed Boise and Pottinger that their investigation had determined that Kessler was likely a fraud, Boies still seemed unaware of the gravity of the situation. According to a source close to the senior ranks of the firm, Boies neglected to tell its executive committee of the scheme and the upcoming exposé in the Times. A spokesperson for the firm says this account and the assertion that the omission raised hackles at the firm are “false.”

If Boies is rattled by his fall, friends say it is impossible for them to know. “He’s a cipher, even in personal relationships,” says one. “He can be very engaging, but he has an impenetrable layer there, where you are not getting inside at all.” Says another: “I think he cares very much about being seen as this great lawyer. But David is a man with very little rearview mirror. You make mistakes; you move forward.”

Although Pottinger did not respond to requests for comment for this article, in the damage control that followed the Times article, Pottinger and Boies Schiller Flexner stressed that Pottinger had notified the F.B.I. and federal prosecutors about Kessler—according to Pottinger, he passed on the information in late September, before the fraud was discovered by the Times. Pottinger has also said that not all his communications with Kessler should be taken literally, as they were part of a strategy to test the con man’s claims. As for Boies, his firm has tried to distance him from Pottinger, alleging that the Times erred in “conflating” separate actions by each lawyer.

But does that get Boies off the hook? Likely not. Some wonder whether Boies’s career will survive this latest blow. Until this month, it was doubtful that Boies would lose important clients; on the contrary, his no-holds-barred defense of Weinstein and Theranos, among others, is likely to attract new ones. But the damage now could be greater. It is no doubt true that lawyers can get away with many things that would not be permitted in civilized society—including offering to withhold information from the public in return for a monetary settlement for their clients’ opponents. But where Boies’s judgment went wobbly, indisputably, was the point at which he invited the Times reporters to witness his discussion with Kessler. If not for that, the whole seamy caper would have remained in the shadows and no one would know about it today. In the end, it seems, karmic symmetry set in: he who rose to such heights with the press also fell at the hands of the press.

Suzanna Andrews is a journalist whose articles have appeared in The New York Times, Vanity Fair, and Rolling Stone