In the basement, a corridor was lined with framed tributes to milestones in his remarkable career:

Westmoreland v. CBS, the landmark First Amendment case; United States v. Microsoft, in which he trust-busted on behalf of the federal government; Bush v. Gore, which needs no introduction; and Hollingsworth v. Perry, the pioneering effort to legalize gay marriage.

Behind glass were a 1986 New York Times Magazine cover story (“The Wall Street Lawyer Everyone Wants”), a 2000 Time article (“Get Me David Boies!”) and one from Fortune in 2010 (“Corporate America’s No. 1 Hired Gun”). Boies’ latest big profile was conspicuously absent. Bloomberg Businessweek had asked in December: “Can his reputation survive?”

The last 12 months have been an unprecedented public relations disaster for the most prominent lawyer in America. In October, his longtime client Harvey Weinstein was branded a sexual predator. Another high-profile client, Theranos, on whose board Boies served, has been exposed as a fraud. The Times publicly fired Boies’ firm, which had been representing the newspaper, after learning that he had been personally involved in an undercover operation to smear Weinstein’s victims and deceive Times reporters. The Manhattan district attorney is looking into the matter and Boies’ role.

In May, “Bad Blood,” the best-selling Theranos exposé by Wall Street Journal reporter John Carreyrou, laid out in gripping detail the aggressive efforts by Boies and his firm to intimidate — and, in some cases, terrify — company whistleblowers. Carreyrou compared the tactics to those of “thugs.”

Of all the humiliation, scolding and criticism Boies has endured, it was this comment that seemed to eat at him as we talked in his study in July — his first extended interview since the furor peaked.

“Overall, his reporting on Theranos was excellent,” Boies said of Carreyrou, between sips of 20-year-old Château Mouton Rothschild, which he had rescued from the cellar. “And overwriting aside, even his personal comments about me were within the realm of fairness. But calling me a ‘thug’ on his book tour was over the top.”

Boies, 77, seemed more puzzled than hurt that editors of The Times, The Wall Street Journal, and Bloomberg had recently spurned his letters to the editor. “I was disappointed,” he allowed, in the same judicious and unflappable manner that has made him a favorite of federal judges. Boies suggested that exonerating facts about his work for Weinstein and Theranos had been omitted from media coverage. “What are letters for,” he asked, “if not to air an opposing view?”

Most of all, Boies said, he felt misunderstood. While he concedes he made mistakes, he maintains he was simply defending his clients’ interests to the best of his abilities, including protecting them from damaging headlines.

“You don’t know all the facts when you take on a client,” he said, “but once you do, you have a duty of loyalty. You can’t represent them halfway. If, as a lawyer, you start to value how you are going to look to the media, as opposed to how your client will look, then you should find a new profession.”

A bedrock of lawful society is that every defendant, no matter how repugnant, has the right to a zealous attorney. But — as he himself has put it — that doesn’t mean the right to David Boies. He can afford to be selective about whom he represents, and he told me that he accepts as clients fewer than 20 percent of the people who approach him.

Throughout his half-century of practice, Boies has shown an almost unerring instinct for picking clients who burnish his reputation. It has made him one of the highest-paid lawyers in the country, with an hourly rate of $1,850. And it has baffled legal observers that, in what could have been his gilded years, Boies ended up representing both Weinstein and Theranos, led by Elizabeth Holmes, in ways that arguably helped prolong their misdeeds. For the first time in his career, the most vaunted advocate in the United States has been a defendant in the court of public opinion.

— ‘The Golden Boy’

One afternoon in August, Boies occupied a prime corner table at the newly reopened Four Seasons restaurant in Manhattan. It was his third meal there in 36 hours. With tousled dark-blond hair and a rather slight build, he looked tanned and relaxed and was looking forward to a safari in Kenya. He was drinking a glass of cabernet from the vineyard he owns in Northern California, visibly relieved that he could again indulge his craving for the Four Seasons version of pigs in blankets.

From his vantage, any clouds over his reputation had dissipated. His firm, Boies Schiller Flexner, was thriving, and he was in demand. In just the first six months of this year, he had generated $35 million in billings. A lawyer for Leslie Moonves, who in early September was forced out as CBS’ chief executive after allegations of sexually aggressive behavior, recently approached Boies to see if he’d consider representing Moonves. Boies demurred, saying, “I don’t think that would be good for Les, and I don’t think that would be good for me.”

Although he’s a Democrat, Boies said he’d be more than happy to represent President Donald Trump in the investigation by Robert Mueller, the special counsel. “Whether you agree with him or not, he needs to have effective representation,” Boies said of the president. “This long, drawn-out morality play isn’t in the country’s best interests. It needs to be resolved. Of course, he’d have to agree to do what I told him.”

Boies said he had no plans to retire. “People retire so they can do what they love to do,” he said. “I already love what I do.” He’s busy on a constitutional challenge to the Electoral College. On a pro bono basis, he’s representing a sex-trafficking victim in a suit against billionaire hedge fund manager Jeffrey Epstein. And he’s one of the lead lawyers representing plaintiffs in a class action against Takata, a manufacturer of defective air bags.

Within the legal establishment, Boies’ reputation seems undimmed. “When you are a superstar like David Boies, there will always be some people who are jealous and want to take you down,” said Jed S. Rakoff, a senior U.S. District Court judge in New York. “I’m not saying that everything he has ever done is beyond reproach, but he has been in my court numerous times and has always performed at the very highest level, both in terms of skill and in terms of professionalism. I think he continues to be very highly regarded by the judges of the Southern District.”

“If you represent people who did bad things, the public is going to lash out at you,” said Theodore B. Olson, a partner at Gibson, Dunn & Crutcher and Boies’ adversary in Bush v. Gore and his co-counsel in the gay marriage case. “David may push hard, but that’s what’s required sometimes.”

Every judge and lawyer I interviewed noted that few laymen fully appreciated their ethical duties. “I often have to explain to journalists that there’s a divergence between legal ethics and the ethics of ordinary people,” said Stephen Gillers, a professor at New York University School of Law and an expert on legal ethics. “Representing a bad person doesn’t make you a bad person.”

Among the general public, however, Boies’ “reputation has absolutely been damaged,” Gillers said. “He may be a stellar lawyer. But in representing a Harvey Weinstein or Elizabeth Holmes, he’s not seeking to vindicate an overarching legal principle as he did in Bush v. Gore or gay marriage.

“Criminal defense lawyers who represent vicious criminals may lead perfectly ethical and admirable lives, but their clients can harm their reputation in the larger community,” he continued. “David Boies can’t represent the Harvey Weinsteins and Elizabeth Holmeses of the world the way he did and still expect the public to see him as a golden boy.”

That’s where Boies finds himself today: still revered by the bar, but fallen in the eyes of the media and liberal constituencies, and undergoing a reappraisal of his career and tactics.

“Anyone who’s been on the other side of his maneuvers knows that he and his firm are incredibly aggressive advocates who push the envelope for their clients,” Carreyrou said. “That was obscured for decades by the fact that he was on the right side of history again and again.”

While Boies projects a sanguine sense of his future, one thing nags at him: who will play him in the film version of Carreyrou’s book. (Jennifer Lawrence is taking on the role of Holmes.) He has been portrayed on stage and screen before, by Ed Begley Jr. in the HBO movie “Recount,” and by Morgan Freeman and George Clooney in productions of the marriage-equality play “8.” Whoever gets the part in “Bad Blood” may be considerably less appealing.

— The Hollywood Upside

Boies got his start at Cravath, Swaine & Moore, the paradigm of the institutional corporate law firm. (We were briefly colleagues there, but never worked on a case together.) Within its staid ranks, Boies was something of a maverick. Usually a little disheveled, he wore off-the-rack Sears or Lands’ End navy suits and a plastic watch strapped over his shirt cuff. He found time for gambling excursions to Las Vegas and cross-country driving trips with his four sons. (He has been married three times and also has two daughters, one deceased.)

At Cravath, staying out of the media was a cardinal virtue. But successfully defending CBS’ “60 Minutes” in a libel suit by Gen. William C. Westmoreland in 1984 made Boies a hero to much of the press. He reveled in the laudatory coverage, and may have been the firm’s most famous partner since former Secretary of State William H. Seward — its only partner who could be deemed a celebrity in his own right.

Boies was drawn to high-profile clients. He tried to bring a young Trump to Cravath, but was blocked by the firm. And he took on George Steinbrenner, the famously irascible owner of the New York Yankees. In 1997, Cravath’s largest account — Time Warner, the owner of the Atlanta Braves — objected to Boies’ representing Steinbrenner. Boies said he wouldn’t abandon a client, and left Cravath to start his own firm: Boies Schiller Flexner.

Liberated, Boies and his firm took on all kinds of clients and embraced fee arrangements, like contingency fees and stock compensation, that weren’t allowed at Cravath. The firm flourished; this year, it had 340 lawyers and average profits per partner of $3.2 million, among the highest in the country.

“I spend a lot of money,” Boies told me: on his Westchester estate and a car and driver; his rare-wine collection; his vineyard; a racing sailboat; a Manhattan co-op in the Sherry-Netherland Hotel.

Four years after he started the firm, in 2001, editor Tina Brown introduced Boies to Weinstein — her partner in a multimedia venture — to discuss a legal memoir. Weinstein hired him, and almost immediately, Boies had to confront the producer’s ugly behavior with women. In 2002, he talked The New Yorker out of publishing allegations of sexual harassment. At the time, none of the victims would go on the record, and Boies argued that the encounters were consensual. Boies knew there had been settlements with some of the accusers: He had shown Ken Auletta, the reporter on the story, copies of the canceled checks from Weinstein’s personal account.

Afterward, Auletta asked Boies how he could represent someone like Weinstein. “I’m loyal,” Boies replied.

He stayed loyal, even as he became aware of the settlements that Weinstein had reached with women alleging inappropriate sexual behavior. “I knew of two or three over the last 20 years,” Boies told me. “Harvey had a reputation as a philanderer. But there was never any evidence or indication of assault, rape or threat of force. He was emphatic that he’d never assaulted anyone or forced anyone to have sex with him.” Boies also helped negotiate a 2015 settlement with a Weinstein employee, Lauren O’Connor, that required Weinstein to seek anger management therapy. (In June, Weinstein pleaded not guilty to assault and rape charges.)

For his part, Weinstein showered Boies with invitations for opening-night parties and celebrity-studded charity events. The Weinstein Co. put one of Boies’ daughters in the hit 2012 film “Silver Linings Playbook,” and also distributed a movie she produced, “Jane Got a Gun.” Along with the son of one of his law partners, Boies formed a film-production company, which invested $5 million each in two Weinstein films, “Gold” and “The Upside,” both flops.

These entanglements may have colored Boies’ objectivity and judgment about Weinstein. But they weren’t, in the legal sense, a conflict of interest. They more closely aligned Boies’ interest with his client’s, which as far as the bar is concerned is a good thing.

— An Impossible Conflict

Boies met Elizabeth Holmes in 2011, after an early Theranos investor asked him to represent her. At the time, her claim that Theranos technology could render an accurate blood test from a finger prick was hailed across Silicon Valley as a breakthrough with enormous profit potential.

“She showed us the lab,” Boies said. “She was very well prepared, committed and intelligent. She made a terrific impression.” A committee of prominent doctors and scientists served on an advisory board.

So impressed was Boies that he took half his and his firm’s fees in Theranos stock, which eventually amounted to 400,000 shares, or roughly $7 million at the company’s apex. Had the company thrived, it could have been worth many times that.

Like his business and social dealings with Weinstein, a financial stake in a client risks coloring a lawyer’s independent judgment. For that reason, firms like Cravath and Gibson Dunn prohibit it. But they are exceptions. It’s a common and lucrative practice, especially among Silicon Valley and San Francisco firms with large venture capital divisions. Defenders of the arrangement note that scores of startups might not have succeeded without the expensive legal advice they were able to finance with stock, rather than cash.

The American Bar Association “has wrestled with the wisdom of the practice for over 20 years,” Gillers said. “The answer that has emerged,” he added, “is that it’s not categorically forbidden, but it has to be monitored closely to protect the client.” To guard against this, clients typically consent to the arrangement in writing, as Theranos did.

Boies insists that his friendship with Weinstein, his personal admiration for Holmes and his firm’s financial interest in Theranos had no impact on his professional judgment, and he seemed somewhat puzzled that anyone would think otherwise. “Anything that gives you an incentive to put the client’s interest first is good for the client,” he said.


During the summer of 2015, at the behest of Jim Mattis, a Theranos board member who is now the secretary of defense, Boies agreed to join the Theranos board. The Wall Street Journal was investigating Theranos, and Mattis told him he anticipated “a difficult period where both Theranos and Holmes would need the advice of a seasoned lawyer,” Boies recalled.

That added another level of ethical complexity. As a board member, Boies assumed a fiduciary duty to shareholders. Now he was obliged to act in the best interest of two different parties: investors and company management. What if one — say Holmes — acted in a way that harmed the other? Precisely because the arrangement could create an impossible conflict, some firms prohibit such board memberships. Yet it is not explicitly forbidden by the bar’s ethics rules.

As The Journal’s Carreyrou stepped up his reporting on Theranos that summer, Boies used all the tools at his disposal to defend Holmes and muzzle the journalist’s sources. His partners sent letters threatening suspected talkers with litigation if they disclosed trade secrets or confidential information. (One whistleblower, a man in his 20s, incurred several hundred thousand dollars in legal fees.) He wrote a 23-page letter to The Journal warning it about publishing Carreyrou’s article.

Boies told me that he maintains a long-standing policy: He won’t sue media organizations, or even threaten to do so. “There may be valid defamation actions, but I don’t want to be the lawyer doing that,” he said. “Going all the way back to CBS and Westmoreland, my experience has been that most reporters try to get it right.” He also has long positioned himself as a friend to reporters and a champion of the First Amendment. He’s a donor to the Committee to Protect Journalists and has served as its annual dinner chairman.

Carreyrou insists that the letter did “explicitly threaten” a lawsuit. Boies denies that, but he seems to be splitting hairs. The letter demands that Carreyrou and The Journal save all their notes and records, which “would doubtless be highly relevant in any lawsuit” — and then cites two cases as precedent. Boies either violated his own policy regarding media lawsuits, or came precariously close to doing so.

When I pressed Boies on this, the litigator in him wouldn’t give an inch. “You don’t write a 20-plus-page letter to threaten someone,” he said. “I could do that in one paragraph. You write that kind of letter to persuade. You may point out things that you believe are inaccurate or reckless and that could support a lawsuit. But it’s not a threat to sue.”

He added: “The question is, can you make the story better, more accurate, more favorable to your client? If so, you’re being an effective advocate.”

From Boies’ point of view, his approach worked. Among the facts that Carreyrou had uncovered, and that didn’t appear in the article, was Holmes’ long-running romantic relationship with Ramesh Balwani, Theranos’ president.

Carreyrou’s article, published in October 2015, was nonetheless a bombshell. “The reporting was excellent. He and The Wall Street Journal deserve credit,” Boies said. “If I knew then what I do now,” he added, “I would have written a very different letter.”

The article didn’t shake his confidence in Holmes, however. She agreed, at his suggestion, to an independent verification of Theranos’ technology in order to rebut the Journal article and reassure investors and regulators.

In early March, she was a guest at Boies’ 75th birthday bash at Las Vegas’ Wynn Resort. But by the end of that month, there were still no results. Holmes began relying on other outside lawyers, and she fired the company’s general counsel, a former Boies Schiller partner, who returned to the firm.

“I’d say that by summer, I wasn’t exactly persona non grata, but I was pretty close,” Boies said. He tried to resign from the board, but other directors dissuaded him. His own outside lawyer advised that as a director, he couldn’t resign in a way that might damage shareholders.

The final straw came in August, when Holmes made an overly optimistic presentation to shareholders without consulting Boies. As he put it in an email to Holmes, he could not continue being her lawyer if she did not heed his advice: “If we are going to risk being at the scene of a serious accident, we want to have the steering wheel in our hands.” He continued, “Because of the very public role we have taken in defense of the company, the firm’s own credibility is at stake.”

Within 72 hours of sending the email, Boies stopped representing the company. He remained a director until Theranos could find a replacement, which took until February. The next month, the Securities and Exchange Commission alleged that Holmes orchestrated a “massive fraud” costing investors more than $700 million and putting the health of its testing subjects at risk.

— An Undercover Operation

Boies’ work for both Weinstein and Theranos might well have gone unnoticed, and his reputation might have remained unblemished, had that been the end of the story. But Boies himself became the subject of further investigative reporting.

Weinstein approached Boies in the spring of 2017, after he learned that Times reporters, as well as Ronan Farrow, then a reporter for NBC News and later for The New Yorker, were unearthing allegations of sexual assault. Weinstein asked Boies to write letters to the publications threatening legal action.

Boies said he told Weinstein that he’d be “crazy” to sue, and reminded him about his personal rule against media lawsuits. But, he said, he agreed to give Weinstein legal advice and act on his behalf as a “friend,” and would not charge him for any of his work.

In his hybrid role as lawyer and friend, Boies approached The Times. He knew many of its reporters and editors, and his firm represented the paper in a libel suit. When The Times retained one of Boies’ partners for the libel case, the company signed an explicit waiver of any conflict, which even gave his firm the right to sue The Times on behalf of another client.

Boies had numerous exchanges with its executive editor, Dean Baquet, maneuvering to get reporters to interview Weinstein on background. Baquet rebuffed him; The Times’ policy is not to talk to subjects of investigative reports on such a basis.

The Times obviously knew that Boies was advocating Weinstein’s point of view, even as his firm continued to represent The Times. What it didn’t know — and what Boies never told the paper — was that he had also negotiated and signed an agreement with Black Cube, a secretive investigative agency that used undercover operatives.

The company’s goal was to dig up “intelligence which will help the client’s efforts to completely stop the publication of a new negative article in a leading NY Newspaper,” as a contract Boies signed put it.

Boies told me that he didn’t view any of this as a conflict of interest with his work for The Times. “Reporters don’t have a monopoly on investigating facts,” he said. To the extent that Weinstein was innocent, he said, it was in both his and The Times’ interest to know that. And even if it was a conflict, he noted, there was the waiver The Times had signed.

When the Times and New Yorker articles appeared in October, Boies said, he was shocked by “the scope of what was involved, the nature of the allegations, including force and rape, and the number of people who came forward, both on the record and anonymously.”

“I think even people who knew Harvey well were shocked,” he added. He called the articles, which won the Pulitzer Prize for public service, “fairly reported, which is what I’d expect from The New York Times and The New Yorker.” At the same time, he said, “it’s not popular to say this, but Harvey is still presumed innocent until proven guilty.”

On Nov. 6, another New Yorker piece by Farrow focused explicitly on Boies’ work for Weinstein, and revealed the contract with Black Cube. Boies was interviewed and confirmed many of the details in the article, which, he told me, fairly presented his views and was “wonderfully well reported.”

Confronted with the Black Cube revelation and the attempt to undermine its own reporters, The Times promptly fired Boies. “We never contemplated that the law firm would contract with an intelligence firm to conduct a secret spying operation aimed at our reporting and our reporters,” The Times said in a statement at the time. “Such an operation is reprehensible.”

“There was really no debate,” Baquet told me recently. “We were outraged. A guy who was working for us was essentially trying to hurt us. It’s not like he was just representing Harvey Weinstein. He was hiring private detectives to deceive journalists. You’d think he’d be ashamed of that.”

Boies said he had no idea that Black Cube’s work would include targeting Times reporters working on the story, but he acknowledged it was a mistake to have hired a firm that he didn’t select and over which he had no oversight or control. “At the time, it seemed a reasonable accommodation for a client, but it was not thought through, and that was my mistake,” he said.

Boies found it difficult to extricate himself from Weinstein. “I’m probably too reluctant to fire clients,” he said. “A lawyer has a lot of leeway in deciding to take a client. But to abandon a client, especially a client in trouble, is a much higher hurdle.” But in November, he said, he and Weinstein “mutually agreed” to part company. Boies said ethical constraints prevented him from saying any more.

— Boies’ Closing Argument

Boies said the #MeToo movement represented a “revolution that’s long overdue,” even though “every revolution causes collateral damage, and to some extent, I’m part of the collateral damage.”

At 77, he is aware that his legacy is at stake. “I guess if it’s a long obituary, this is going to be in there,” he said at lunch at the Four Seasons, referring to the Weinstein and Theranos controversies. “In the context of 50 years of a high-profile law practice, there are going to be things that make people unhappy. Any time you go through something like this, you reflect on what you might have done differently.”

But he added: “For 99 percent of the people I deal with, this doesn’t affect them. For some people, mostly in the media, it does affect them. I get that.”

Of course, I’m in the media, writing for his former client The Times, but he’s not advocating on behalf a client. He’s defending himself. I asked him what that felt like.

“Steve Jobs told Walter Isaacson” — his biographer — “that he wanted his children to understand him,” Boies said. “I get that. When you’re talking about yourself, you tend to be less of an overt advocate. If you want people to understand you, you have to be accurate and complete, blemishes and all.”

I asked him to assume I’m the judge and readers the jury. What’s his closing argument? He seemed to relish the challenge.

“I’m proud to be a lawyer and to serve the justice system,” he began. “That’s essential to everything we care about: liberty, equality, inclusiveness, the pursuit of happiness. The justice system protects the weak and limits the strong.

“In America, this is an adversarial process,” he continued. “In many countries it’s not. History shows that no system does more to protect individual rights and liberties than a system that provides people with a lawyer with complete dedication to the client.

“A lawyer can choose what clients to represent. A lawyer does not have the choice of how to represent a client. A lawyer is duty- and honor-bound to represent a client effectively and aggressively, within the bounds of the system itself. And once a lawyer takes on a client, you do not have the right to abandon that client under fire, except in extraordinary circumstances.”

By now he had hit his stride. “If we decide any class of accused is not deserving of aggressive representation simply because of what they’re accused of, then we undermine the protections that are essential for all of us.”

This was Boies the legendary litigator, spontaneously generating fully formed paragraphs. Evidently, though, Boies felt he had not made himself fully understood, and a few days later, he wrote me an email of more than 1,000 words.

“Like I often do following a particularly good discussion (or movie or play), I keep thinking afterward about what we covered,” he began. Doing so seemed to trigger, for the first time in our interactions, an element of wistfulness.

Without naming names, but obviously referring to Theranos and Weinstein, he conceded that “greater due diligence would have led me to decline the representation” of one. Of the other, “I think I have to acknowledge that I have let loyalty to a client often outweigh revelations that, had I known them earlier, would have led me not to accept the representation initially.”

“I don’t know whether any of this adds anything to what you have,” he concluded. “But it has helped me think through how I feel about these issues.”

This article originally appeared in The New York Times.

James B. Stewart © 2018 The New York Times