F. Lee Bailey, a swashbuckling, high-flying defense attorney whose celebrity often eclipsed that of his famous clients, but whose legal career crashed under the weight of financial fraud, personal bankruptcy, and disbarment, died Thursday in Georgia. He was 87.
His death was confirmed by his former law partner, Superior Court Judge Kenneth J. Fishman.
A Waltham native and Boston University Law School graduate, Mr. Bailey was for decades the model of the modern gun-for-hire criminal defender, a brilliant, pugnacious counselor whose courthouse presence all but guaranteed legal fireworks.
Beginning in the early 1960s, he attracted a roster of clients whose names and deeds, alleged or proven, commanded front-page headlines.
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Prominent among this group were O.J. Simpson, on whose legal “Dream Team” Mr. Bailey served as co-counsel; Albert DeSalvo, who confessed to being the notorious Boston Strangler; publishing heiress and kidnap-victim-turned-bank-robber Patricia Hearst; Army Captain Ernest Medina, implicated in the Vietnam War’s infamous My Lai Massacre; and neurosurgeon Sam Sheppard, whose arrest after his wife’s murder inspired the television series and hit film “The Fugitive.”
Mr. Bailey’s courtroom countenance was striking, augmenting his reputation as a pitbull criminal defender. Of modest height and stocky frame, sporting bushy sideburns and custom-tailored suits, he projected an outsized personality. At the same time, he deployed an arsenal of legal skills — florid oratory, a near-photographic memory, an innate flair for theatrics — to maximum effect.
There was little of the genteel Atticus Finch in Mr. Bailey, certainly. He was known to question witnesses mercilessly, battle with judges and prosecutors ferociously, and suffer from lack of ego rarely if ever, no matter the trial outcome or verdict in the court of public opinion.

The Simpson case fit that template. Accused of two brutal murders, the former football star faced almost certain conviction, based on evidence collected at the crime scene and presented in court. That is, until his high-priced defense team set out to prove police bias.
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It fell to Mr. Bailey to interrogate Los Angeles police Detective Mark Fuhrman, and it was his punishing cross-examination of Fuhrman, boring in upon his history of using racial slurs, that helped sow enough doubt in jurors’ minds to secure a not-guilty verdict for Simpson.
His surprising, if not shocking, acquittal cast a shadow over Mr. Bailey’s later career, however, even as he continued to insist years later that Simpson was innocent of the crimes. (He theorized that Nicole Brown Simpson, O.J. Simpson’s ex-wife, was the victim of a mistaken-identity drug-related hit.)
“Among the rednecks of America, which there are many more than people seem to realize, it was terribly damaging,” he said, looking back on the trial’s effect on him personally. “I got blamed for O.J.’s acquittal.”
In most cases, Mr. Bailey was unapologetic about the clients he represented and the methods he employed to defend them.
“I get paid for seeing that my clients have every break the law allows,” he once asserted. “I have knowingly defended a number of guilty men. But the guilty never escape unscathed. My fees are sufficient punishment for anyone.”
Away from court, Mr. Bailey burnished his own legend incessantly. He wrote best-selling books, hosted TV specials, lectured widely, piloted airplanes and helicopters, and starred in commercials for vodka and mattresses, two consumer items with which he was admittedly well acquainted.
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“He was a celebrity lawyer, no question,” said veteran Boston attorney Joseph Balliro, a longtime friend and occasional legal ally. “From day one, Lee also was the best criminal defense lawyer I’ve ever known. Nobody comes close, and I’ve known many exceptional ones.”
Mr. Bailey’s knack for attracting media attention (and media-related deals) mostly served him well, although not always. Most notably in the Patricia Hearst case — following her conviction on bank robbery charges, she accused Mr. Bailey of drinking on the job and signing a lucrative book deal before the trial even began — it called into question his pursuit of personal gain over client service.
In his best-selling book about the Hearst case, attorney-author Jeffrey Toobin noted as much, writing that Mr. Bailey’s “hunger for money dwarfed even his lust for fame.”
At the height of his wealth and celebrity, Mr. Bailey maintained offices in Boston, New York, and Florida, and owned an interest in dozens of airplanes, helicopters, vintage cars, and boats. His emergence as a pop-culture figure was not accidental, either. In the 1960s, he hosted a celebrity interview show, “Good Company,” and a program investigating the “Paul is dead” mystery. (Beatle Paul McCartney was then, and is still, very much alive). He also appeared in prime-time TV series, made the covers of Time and Newsweek, sat for an ego-stroking Playboy interview, and published a novel, “Secrets,” in 1978.

In 1966, Mr. Bailey moved into a palatial Marshfield house, his home base for two decades. Built on 3½ hilltop acres, the 12,000-square-foot structure featured a helicopter hangar (he commuted to his Boston office by chopper) and indoor and outdoor swimming pools. He sold the property in 1985 and later owned a home in Lynn.
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Mr. Bailey’s own legal troubles began in the 1970s, when he defended a businessman named Glenn Turner, who stood accused of running a fraudulent self-help pyramid scheme. A grand jury investigation into Mr. Bailey’s conduct led to his indictment on bank fraud charges. Although he was acquitted — appearing on his behalf was future Dream Teamer Alan Dershowitz — the affair cost him dearly, monetarily and otherwise.
In 1982, Mr. Bailey was arrested in California on a DWI charge. He was represented by Robert Shapiro, who later brought him onto the Simpson defense team. After his acquittal, Mr. Bailey published a payback book titled “How to Protect Yourself Against Cops in California and Other Strange Places."
By the mid-’90s, Mr. Bailey’s legal career was floundering, his personal affairs and finances unraveling.
Claude Deboc, a former client, had pleaded guilty to drug smuggling. To cover Mr. Bailey’s fees, the government let him hold $6 million in stock owned by Deboc. When its value more than quadrupled, government officials insisted the profits belonged to Uncle Sam, not Mr. Bailey. He vehemently disagreed, citing a verbal agreement that could not be independently validated.
By that time, Mr. Bailey had already spent $4.6 million of the stock proceeds. He was jailed for 44 days and fined $3.5 million.
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Testifying against him this time was Shapiro, with whom he’d suffered a bitter falling out after the Simpson case.
In 2001, Mr. Bailey was disbarred in Florida on multiple counts of judicial misconduct. Massachusetts swiftly followed suit. His final attempt at a career comeback came in 2012 after moving to Yarmouth, Maine. He passed the state bar exam, but Maine’s board of examiners refused to admit him. A successful appeal was rejected by the Maine Supreme Judicial Court, which narrowly held that Mr. Bailey “minimizes the wrongfulness and seriousness of the misconduct for which he was disbarred.”
He never practiced law again.
Francis Lee Bailey was born and raised in Waltham, one of three siblings. His mother was a schoolteacher and nursery school founder, his father a newspaper ad salesman. They divorced when Lee was 10.
A talented hockey player, Lee Bailey attended two private New Hampshire schools, Cardigan Mountain and Kimball Union Academy, before enrolling in Harvard College, where he was admittedly an indifferent student. He dropped out to join the Navy, then transferred to the Marine Corps, where he learned to fly jet planes. While there, he became a legal officer in training and wound up handling nearly 200 cases during his military service.
Accepted by Boston University Law School in 1957, he simultaneously opened his own investigative firm. Soon after his graduation in 1960, he landed his first prominent case, defending an auto mechanic named George Edgerly, who stood accused of murdering his wife.
The case foreshadowed much of Mr. Bailey’s future work as an ace legal strategist. He hired a polygraph expert — a tool Mr. Bailey himself excelled at using — and not only won a not-guilty verdict but garnered sufficient press coverage to attract a steady stream of future clients.
Among them were Dr. Carl Coppolino, charged in 1965 with murdering his wife and the ex-husband of his mistress (he served 12 years in prison); the families of passengers killed aboard a Korean Air Lines flight shot down over the Soviet Union in 1983; and Panamanian strongman Manuel Noriega.

The case of the Boston Strangler was another headline-grabber. It involved the rape and murder of more than a dozen women in the Boston area, crimes committed over a period of 19 months. Albert DeSalvo, arrested after a series of notorious sexual assaults, eventually confessed to the Strangler murders while sitting at Bridgewater State Hospital, yet police did not have enough evidence for the murder charges. So Mr. Bailey defended him on the rape charges, for which DeSalvo drew a life sentence. He recanted the confession before he was killed while in prison, in 1973.
The Hearst case provided another publicity-rich venue for Mr. Bailey’s talents, but its outcome proved to be a mixed bag for the defense — and a watershed of sorts for Mr. Bailey himself.
Patricia Hearst was kidnapped in 1974 by members of the radical group the Symbionese Liberation Army. She was held captive for 19 months, during which she participated — willingly, it seemed — in several crimes, including a bank robbery in which one bystander was killed.
At trial, Hearst claimed she’d been brainwashed by her captors. Mr. Bailey got first-degree murder charges dropped in exchange for her testifying against other SLA members. Hearst was given a seven-year prison sentence and served less than two years behind bars. (Her sentence was commuted by President Jimmy Carter; President Bill Clinton later granted her a full pardon.) She later charged Mr. Bailey with erratic behavior and rendering ineffective counsel.

Mr. Bailey’s personal life also contained its share of turbulence. He married four times, three ending in divorce. A fourth marriage, to Patricia Shiers, ended with her death in 1999.
Lynda Hart, his third wife, once said of Mr. Bailey, “The only thing he couldn’t resist was temptation.”
Mr. Bailey leaves three sons, Bendrix of Rochester, Brian of California, and Scott of Atlanta; a sister, Nancy of Chelsea; and five grandchildren.
Bendrix said that while “much of what’s spoken about him and written about him is the sensational aspect of his career,” often lost in the discussion is how his father’s success with certain cases still resonate today.
For example, Mr. Bailey appealed Sheppard’s murder conviction to the US Supreme Court, which ruled he did not receive a fair trial due to extensive publicity — a factor that now regularly receives considerable attention. Sheppard was found not guilty in a retrial.
And while Mr. Bailey had considerable success obtaining not guilty verdicts, Bendrix said, there is “a subtle point that’s important to understand. The only thing F. Lee Bailey did better than other people was to get people like Mark Fuhrman to reveal the truth that they would rather keep secret, and then the juries and the judges decide what to do with the accused. No great lawyer gets anybody off. What a great lawyer does is get the truth out so the jury can make a decision.”
In Maine, where Mr. Bailey became well known to his Yarmouth neighbors, he ran a business consultancy with his longtime partner, Deborah Elliott, operated out of offices located above her hair salon.
In 2017, facing a $5.2 million tax liability, Mr. Bailey filed for Chapter 7 bankruptcy protection. He again blamed his legal woes in part on his role in the Simpson case, telling Town & Country magazine that he and Dershowitz “have the O.J. curse in common, to a degree.”
“I don’t have a very lavish life,” he told a Globe reporter in 2016. “But I sleep well.”
Joseph P. Kahn can be reached at josephpkahn@gmail.com. Bryan Marquard of the Globe staff contributed to this report.