Bob Silver, the man David Boies called “my brain,” dead at 58

February 8, 2015, 4:00 PM UTC
Photograph by Lindsay McCrum

Last Monday morning Robert Silver, the longtime right-hand man of David Boies, the most famous trial lawyer in the country, was found dead in his hotel room at the Four Seasons Hotel Miami, where he had been living for about six weeks. He was 58.

Silver was a brilliant, kind-hearted man who struggled with physical and emotional challenges.

The cause of his death is under investigation, a spokesman for the medical examiner said in a voicemail, which is expected to require “a number of weeks for resolution.”

Boies, 73, and his son, Christopher, 46—also a close friend of Silver’s—said in telephone interviews that, based on conversations with police and medical examiner personnel, there were no indications of suicide or foul play, and the presumed cause of death, pending the report, is a heart attack. (The medical examiner’s office and Miami police department declined to provide any specifics to Fortune.)

Boies and his son are both partners at Boies Schiller & Flexner, the firm Boies founded in 1997 with three other partners, including Silver.

Though Silver lived in New York, in an apartment on East 57th Street, and was working on post-trial briefs for a case being heard in Washington, D.C., he was living in Miami so “he could get some relaxation when he wasn’t burning the midnight oil,” Boies explains in an interview.

A few hours after Silver’s body was found, on February 2, Boies wrote a short email to the firm announcing the death. “Bob was a great person, a great partner, and great friend,” he wrote. “Much of what I have been able to accomplish, and much of what this firm has been able to achieve, has been due to Bob.”

In the past, Boies has sometimes introduced Silver to others as “my brain.” For 30 years, Silver was the consigliere’s consigliere.

Performing his half of a uniquely productive, symbiotic relationship, Silver helped research, strategize, synthesize, and prep most of Boies’s signature trials of the past four decades. Boies then absorbed, sharpened, and executed Silver’s work in the public arena of the courtroom.

In this manner, Silver helped map out Boies’s representation of Texaco in a $10.5 billion dispute with Pennzoil in the 1980s (a lot of money at the time); defend CBS against the defamation suit of Gen. James Westmoreland, the Vietnam War commander; win $1.2 billion for the Federal Deposit Insurance Corporation from Michael Milken and Drexel Burnham Lambert for their alleged role in the S&L crisis of the 1980s and 1990s; prosecute the government’s antitrust suit against Microsoft; unsuccessfully defend file-sharing pioneer Napster against the recording industry; represent Vice President Al Gore in the historic Bush v. Gore vote-count contest of 2000; mount the suit that, in 2013, struck down California’s Prop 8, which had forbidden same-sex marriage; and, at the time of his death, press Maurice “Hank” Greenberg’s attempt to win $17-40 billion in reimbursement from the government, for allegedly having wrongfully seized his property during the financial crisis of 2008, when it bailed out AIG (AIG), the insurance company he founded.

“[Silver] had tremendous intellect, tremendous objectivity, and enormous abilities and productivity,” Boies says in an interview. “But he was also one of the most decent, endearing, honest people you could imagine. He was a model of what not only lawyers, but people, should be.”

Ralph Isham, an investment banker who remained close to Silver ever since they were roommates at Yale, calls him “the most brilliant person I’ve ever known, and the kindest-hearted as well.”

Another close friend, the British-born journalist, editor, and publisher Sir Harold Evans, 86, calls him “exhilaratingly clever, a conceptual thinker of the highest order, who also nurtured a gene for altruism.”

Evans, the former long-time editor of The Sunday Times of London, and his wife, former New Yorker, Vanity Fair, and Daily Beast editor Tina Brown, met and befriended Silver on a chartered plane flight returning to New York from Boies’s 65th birthday party in Las Vegas in 2006.

In an interview, Evans says that Silver first impressed him on that flight with his insights on free speech law not just in the U.S., but also in Britain and Europe–a subject to which Evans had given much thought, due to lawsuits involving the Times.

Evans later learned, he recounts, that “Bob had a passion to help people with physical or mental disabilities.” He remembers attending a gala benefit with him at which participants were asked to sponsor a $4,000 scholarship. “Bob raised his hand,” he recalls, “which would have been generous. Then he bought a second, and then a third.”

Another long-time friend asserts that Silver exhibited “almost pathological generosity.” This friend says he once insisted on taking the lavish gifts Silver brought to a child’s birthday party back to the store, so he could restore the money to Silver’s credit card.

The source’s use of the phrase “almost pathological” is not a joke. He and several others interviewed for this article remembered Silver as a “troubled soul,” who went through depressive, reclusive phases.

Isham says Silver was sometimes “tormented,” in that he “never thought he was good enough. He was self-confident intellectually, but not at all emotionally.”

A different source, who knew him at Yale Law School, says he struggled with serious bipolar-like symptoms at that time.

Another long-time friend, who requested anonymity, asserts: “Bob had some kind of mental illness. He went through these patches and came out again, as if it never happened. Bob couldn’t quite keep it together for extended periods of time.”

This friend recounts that there were times when he received emails from Silver in which “the language would become disconnected” and “delusional.” It was “literally impossible to sense what he was talking about,” he says.

Others interviewed for this article, however, including David and Chris Boies, reject the “mental illness” label, though they acknowledge extreme, and sometimes unhealthy perfectionism.

“He would create something beyond the capacity of almost any other person,” Boies says, “and then stay up all night trying to refine it, to make it better. Those qualities, taken to the extreme, can be extremely wearing and stressful on a person. I do think he would’ve been happier if he learned to appreciate and celebrate his many accomplishments, as opposed to being driven to always try to do more.”

Silver also suffered from physical issues. He was periodically a chain-smoker, sometimes drank too much, and his weight fluctuated markedly. For the last 15 years he had suffered from severe back problems, first triggered when his chair fell off a podium at a conference. He underwent two back surgeries in the last 10 months of his life. He had been an excellent, competitive tennis player, who craved physical exercise, so the injury was torturous.

Just about a week before his death, though, Evans says he received a very upbeat email from Silver vowing to try to play table tennis with him when he returned, and promising to send Evans a draft of the court papers he was preparing.

Silver grew up in Levittown, New York, on Long Island. His father was an aeronautics engineer, of Russian Jewish extraction, and his mother was a psychiatric nurse, of Turkish Jewish background.

According to Silver’s second ex-wife, Teresa Melhado, Silver had been a gifted musician growing up, playing cello and piano and even conducting a chamber music group as a teenager.

Having skipped two grades, he entered Yale College at 16. According to those who knew him then, including Isham, he was estranged from his parents. He also rarely mentioned his siblings: a younger brother Jeffrey, who died in 2012, and a sister, Rebecca, who survives him.

In 1976, at age 20, he graduated summa cum laude with both a bachelors and masters degree the same year. He embarked on a Ph.D. thesis in philosophy, but switched before completion to the joint degree program at Yale Law School and Yale School of Management.

In 1981, he served as a summer associate at Cravath Swaine & Moore—then one of the country’s top two or three corporate law firms in terms of both prestige and partner earnings. Boies, who had recently returned to Cravath after a period as chief counsel for the U.S. Senate Judiciary Committee, selected Silver to work with him based on his extraordinary resume. They clicked.

Silver returned to Yale, picking up his J.D. and M.P.P.M (master’s of public and private management) in 1982. He spent a year at a coveted clerkship for U.S. Court of Appeals Judge Jon Newman, and then returned to Cravath full-time in 1983.

There, he worked for several top partners, in addition to Boies, including the firm’s legendary litigator Thomas Barr. Though all Cravath associates worked dauntingly long days, Silver developed a reputation for putting in frightening, nearly unimaginable hours, a former colleague recounts.

In 1988, he left Cravath to become a faculty fellow at Yale Law School. Cravath partner Barr, a Yale Law alumnus, helped arrange this placement at a time when Silver was struggling with bipolar symptoms, according to a person who knew him at that time. (Barr died in 2008.)

Later, Silver served relatively short stints with two other first-rate law firms, and then spent about a year-and-a-half on his own, consulting for several firms.

While at the second of those law firms, in 1993, Silver married Eva Assimakopoulos (now Eva Lana), but the couple divorced in 1995.

On May 14, 1997, Boies did the unthinkable for a Cravath partner of that era: He left to form his own firm. Silver joined him the next day.

“The first person I got to work with me was Bob,” Boies says.

Three months later, Boies and Jonathan Schiller formed Boies Schiller, with Silver and William Isaacson as the only other partners. (Donald Flexner joined the firm as the third name partner in December 1999.)

When the firm formed an executive committee in 2001, Silver was named to it, and he served on it till his death. (Boies Schiller & Flexner today has about 250 lawyers. Last year it was the ninth most profitable law firm in the country, according to The American Lawyer, with an average partner making nearly $3 million a year.)

In the early days of Boies Schiller, Silver was the person reporters like me went to first, when we wanted to gain entrée to Boies, or to understand his cases. Silver was available at every hour of the day, courteous, good-humored, impeccably dressed, unpretentious, never arrogant, never condescending, and astoundingly articulate. Later, as the firm grew, and hired a spokesperson, Silver became less visible to reporters.

In August 2009, Silver’s neglected private life took a joyous turn. At a wedding at the Southampton home of Louise Grunwald—whose second husband, Henry, was once editor-in-chief of Time Inc.—Silver married Teresa Melhado, a widow. Melhado had been a lawyer in Texas and a financial reporter until her first marriage.

“I adored him,” says Melhado of Silver, in an interview. “He was the sweetest, kindest man. I never heard him say anything mean about anyone.”

“He was just brilliant,” she continues, “but really humble. He would come out with the most amazing things. He’d reel off a quotation from a poet you never knew he’d read. All this knowledge, but he wasn’t trotting it out. It would just pop out by accident.”

Melhado’s first husband had died young, of brain cancer, leaving her with three children. Silver became their surrogate father, she says, “jumping in with both feet.”

“They adored him,” she continues. “It was mutual.”

Melhado asks that I not portray Silver as a “drone” or “grind” who slaved away behind the scene. He was stylish, and funny, a joy to be with, she says—“a snappy dresser, sensitive to esthetics.”

“He loved the show Mad Men,” she says, “with the well-dressed, chain-smoking men of that era. Huge lunches of red meat. That was Valhalla for him.”

By all accounts the marriage made Silver extremely happy. But the couple separated in December 2011, and divorced in January 2012.

It was her decision, and it crushed him. (She declines to discuss the reasons.)

“He was mystified as to why it broke up,” says Boies.

Last September, the case known as Starr International v. United States, in which Boies’s client Hank Greenberg is attempting to recover billions of dollars from the government, went to trial in Washington, D.C. Though in the past Silver often sat at counsel table when Boies tried a case, passing him notes, he did not do so this time. Though he had prepared for the trial for about three years, he did not attend an hour of it. This was so, even though the case had tantalizing box-office appeal to even the most casual observer of current affairs, with Boies cross-examining a Who’s Who of the financial crisis, including Hank Paulson, Tim Geithner, and Ben Bernanke.

“He would have loved to come and sit at trial,” Boies says, in explanation. “But he felt it was much more critical to get the preparatory work done,” he says. “Bob was always someone who made decisions never based on what was in his personal interests. He was totally focused on what was best for the case. . . . Time and time again, he put the interests of the firm, my interests, the interests of the case, the interests of the client, way ahead of his own.”

In December, after Boies Schiller held its annual firm meeting in Key Biscayne, Silver chose to stay in a hotel in Miami while working on post-trial submissions in the Starr case. That’s where he was when his body was found last Monday.

In our conversation, Boies noted that sometimes, when he and Silver were relaxing, at a dinner or a ballgame, he’d urge Silver to take more time off to enjoy himself. “See how much fun you’d have?” Boies would tell him, he recalls.

On one occasion, Boies says, Silver responded with a joke.

“If I could take time off more easily,” Silver said, “I’d be normal. And you wouldn’t want me normal, would you?”

Correction: The original version of this article mistakenly said that Silver’s first marriage occurred while he was still at Cravath. In fact, as the text now reflects, his first marriage was later, in 1993, and ended in divorce in 1995. I regret the error.

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