Lee Bailey is forever ready to share brutal opinions on the lawyers who have crossed him over the years. Marcia Clark, who in the midst of a row during the O.J. Simpson trial called him a liar? “A harridan,” he growls. His Simpson co–defense counsel and ex-friend Robert Shapiro? “At least mildly sociopathic.” David McGee, the United States Attorney from Florida who doggedly pursued Bailey for helping himself to millions of dollars the government said was not his to spend? “Totally dishonest.”

If F. Lee Bailey’s your lawyer, you’re his friend, you’re his client, and you’re innocent.

When former Dream Teamers, as Simpson’s lawyers were known, failed to publicly proclaim the ex–football star’s innocence following the 1997 wrongful death civil judgment against him, it felt like pure treachery. “Barry Scheck caved, told Newsweek you have to respect the civil verdict, which you don’t, and he never should have said it,” Bailey says.

Bailey and Simpson during the 1995 trial. Getty Images

By the time Simpson went on trial in 2008 on charges that he had liberated several items of his old sports memorabilia at gunpoint from a man in a Las Vegas hotel room, Bailey was the only one of those lawyers Simpson was still in touch with and, seemingly, one of the last people on earth still willing to assert publicly that the onetime legend hadn’t murdered his wife. They talked on the phone several times before and during the 2008 trial.

Having been disbarred in 2003, the old gunslinger Bailey could offer only informal advice. Fire your lawyer, he implored Simpson, who refused to listen. A jury convicted him on all 10 counts, and he was slapped with a 33-year prison sentence. Bailey hasn’t heard from Simpson since the conviction; he says he was told that Simpson was warned by prison officials to steer clear of Bailey if he wanted to get on the good side of the parole board.

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Simpson will likely be let out this year after serving nine years behind bars. Bailey hopes he’ll call. “I’m convinced the guy got screwed,” he says.

Bailey readily catalogs the failings of others, but he takes a rare reflective pause before addressing what he might have done differently to avoid his own current predicament: broke, disbarred, his legacy as one of the finest trial lawyers in American history imperiled by two decades of controversy.

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“At 83, that’s an almost impossible question to answer,” he says, his single malt baritone worn raspy by decades of dominating courtrooms and conversations. “I would do things differently only with the benefit of hindsight, and that’s a chance that life never gives you. At the time I did things, I thought they were right.”

Bailey sips a glass of pinot grigio at lunch one fall afternoon at the Royal River Grill House, his favorite restaurant in his adopted hometown of Yarmouth, Maine, just north of Portland. He’s a celebrity there and, to his obvious pleasure, much fussed over. On his way in, Bailey stops a waitress in the midst of pouring a drink to tell her that he has brought press from a national magazine.

“If the magazine had a gatefold, I’d get you in it,” he says.

Next to him sits Debbie Elliott, his girlfriend of seven years. “A pretty good-looking 62,” he remarks, an accurate assessment of the curvaceous salon owner, who is dressed in head-to-toe black, her platinum blond hair pulled back in a ponytail. Bailey, who in the 1970s wore sideburns so bushy they resembled a barrister’s wig, now has thin white hair clipped close to the scalp, a side effect of cohabitation with a hairdresser.

Bailey and Elliott fell first in love, then into business, taking over the little apartment above Salon Debbie Elliott in a two-story shingled building in Yarmouth to open a business consultancy called Bailey & Elliott. Bailey often offers clients advice while Elliot trims their hair. “It’s very convenient,” he says.



I enjoy being F. Lee Bailey,” Bailey wrote in his 1971 best-seller, , the first of his 20-some books. Despite the legal and financial difficulties that have bedeviled him, he clearly still can’t help enjoying it. When he wrote those words he was 38 and the most sought-after criminal defender in the country. A trio of high-profile court victories landed him on the cover of Newsweek in 1967, just six years out of law school.

I enjoy being F. Lee Bailey.

Most notably Bailey had fought all the way to the Supreme Court to overturn the conviction of Sam Sheppard, a neurosurgeon imprisoned for killing his pregnant wife (the case would inspire the movie The Fugitive). Bailey successfully argued that prejudicial media coverage of Sheppard’s 1954 trial had tainted the jury and created, in the court’s opinion, a “carnival atmosphere”—ironic given that Bailey, in order to sway public opinion so that Sheppard would be allowed a polygraph test, went on The Mike Douglas Show and strapped comedian Dody Goodman into one of the machines.

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Bailey delighted in flaunting the trappings of his status. In his first book he wrote of his “intelligent, unreasonably attractive blonde” second wife, Wiki, and the Lear jet he piloted around the country. “Money can buy a certain amount of happiness,” he wrote in his second memoir, in 1975, cataloging those happinesses: a Mercedes 350SL, a Citroën SM, and a helicopter that he could land inside the circular driveway of his property in Marshfield, Massachusetts, an aircraft that at the push of a button would be plucked up by a space age assembly and deposited safely inside a hangar.

By then he had moved on from Wiki and married a Kiwi, stewardess Lynda Hart. He would meet his fourth and final wife, Patty Shiers, a United Airlines stewardess, on a flight from Boston to San Francisco in 1976; for at least one day Lynda unwittingly sat just a few seats from her husband’s next wife in the gallery at Patty Hearst’s trial. “Lee was a handful,” Lynda, who has remained friendly with Bailey, tells me. “The only thing he couldn’t resist was temptation.”

America’s most notorious living lawyer can’t practice law. In 2001, Florida tossed him from the bar for taking millions of dollars in trial compensation that the government claimed was not his, and two years later, the state of Massachusetts, where he began practicing in 1961, reciprocally disbarred him.

Bailey moved to Maine, and in 2012, at the age of 79, walked into a classroom and took the bar exam. “I didn’t work that hard, and I passed it at the top of the pack,” he says—but then Maine’s bar rejected him as well. Bailey is broke, too. Last June, unable to settle a $5.2 million tax bill, he filed for Chapter 7 bankruptcy, disclosing that all he had to his name was a gold 1999 Mercedes station wagon worth less than $2,000, sundry effects worth around five grand, and a modest condo in Yarmouth on which he carries a $365,000 mortgage.

“It’s a terrible tragedy,” says Alan Dershowitz, who has known Bailey for 40 years and who served with him on O.J. Simpson’s so-called Dream Team. “I have seen lawyers who have done so much worse allowed back in after a couple of years.”

Dershowitz believes that Bailey is being made to suffer for Simpson’s acquittal. “Without a doubt,” Dershowitz says. “I think it was a major factor in the vindictive way in which he’s been treated.” Bailey too sees the beginning of his own end in the Simpson acquittal. “People at every level, judges on down, pointed the finger and said, ‘If you hadn’t prostituted your talents for this guy, he would have gone to jail.’ ”

Lee Bailey points at defendant, O.J. Simpson, during the Simpson murder trial. Getty Images

Bailey’s self-assigned role as “last one standing” of the surviving Simpson attorneys to still proclaim his client’s innocence is totally unsurprising to Dershowitz. “If F. Lee Bailey’s your lawyer, you’re his friend, you’re his client, and you’re innocent,” he says. “He’s the only lawyer who does that. He doesn’t play the game the rest of us play: ‘Oh, I don’t know whether he’s guilty or innocent, but I’m giving him the best possible defense.’ Bailey is totally convinced that O.J. was innocent.”

Bailey is totally convinced that O.J. was innocent.

Bailey’s pet theory: Faye Resnick, Nicole Brown Simpson’s frequent houseguest, who happened to be holed up in rehab for cocaine addiction on the night of the murder, was the intended target of a drug-related hit. His investigators heard rumors that Resnick owed drug dealers $30,000, a theory the defense introduced in the trial.

“We think the killers came to look for Faye Resnick, who was also blond, and, typical of hitmen, they were dumb enough to mistake Nicole for Faye Resnick,” he says. He dismisses as “doctored” the overwhelming photographic evidence offered in the civil trial of dozens of images of Simpson wearing the Bruno Magli loafers—the “ugly-ass shoes” Simpson denied under oath ever owning—shoes whose distinctive bloody tread marks were all over the crime scene.

In Simpson, Bailey admits, he sees something of himself: a great man brought low by false accusations. “I don’t think he got fairly treated, and I don’t think I got fairly treated,” he says. “If that’s not a level of kinship, it’s certainly a level of identity. We have the O.J. curse in common, to a degree.”

Last year’s O.J. television orgy provided a relitigation of the case and another go in the spotlight for Bailey. ESPN’s damning O.J.: Made in America, which used only a snippet of the hours of interviews he sat for, was “really bad,” he says, incriminating Simpson with “the real dregs” of O.J.’s social circle. FX’s The People Versus O.J. Simpson was better, but Bailey wishes Nathan Lane had visited him in Maine before portraying him. He has long had a book arguing Simpson’s innocence ready, but, he laments, “the publishing industry does not want a book favorable to O.J.”

Lee is often wrong but never in doubt,” Grace Mitchell would say of the eldest and most difficult of her three children (the F is for Francis). Indeed, innocuous parts of Bailey’s biography are fodder for endless lawyerly debate. His childhood friend and longtime law partner, J. Albert Johnson, recalls seeing the young Bailey, a rare middle-class kid in working-class Waltham, Massachusetts, decked out in a Little Lord Fauntleroy getup.

“He made that up,” Bailey says. “I never wore a Little Lord Fauntleroy outfit.” But Johnson is insistent. “I’ve seen a picture of him in the Lord Fauntleroy outfit,” he says. “I can tell you where it was in his home.”

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From the beginning, Bailey’s gifts as a lawyer appeared almost supernatural. He was a lethal cross-examiner and a prodigious pretrial crammer, and he would often astonish judges by reciting from memory not only case law but the page numbers where the citations could be found.

“He’s just brilliant, that’s all,” Johnson says. “I couldn’t keep up with this guy. Most of us mortals are lucky to go 20 miles an hour. Lee Bailey’s brain goes a thousand miles an hour, so quick that he becomes frustrated with those who cannot keep up.” Indeed, Bailey says that he scored 162 on two childhood IQ tests—a number higher than Albert Einstein’s. Jurors loved him, especially women; “Bailey types,” they called them in his office.

He’s just brilliant, that’s all. I couldn’t keep up with this guy.

He drank deeply of the fame that floated his way and accepted offers no lawyer before him had entertained. He agreed to play himself in a dramatization of the Sheppard case (it was never made), he grilled Tony Curtis on a short-lived ABC interview show, and in 1969 he hosted a televised mock trial to determine whether Paul McCartney was indeed dead. On 1983’s Lie Detector, Bailey and a polygrapher let the machine settle such burning questions as whether Ronald Reagan’s barber was telling the truth when he said the president didn’t dye his hair.

Still, trouble shadowed him. In 1970 a Massachusetts judge censured him for carping about a guilty verdict on The Tonight Show, remarking that Bailey had “self-esteem of such proportions as to challenge description.” Then, in 1973, Bailey was indicted and charged along with a huckster client, Glenn Turner, for helping run an Orlando-based pyramid scheme. Bailey walked, but he blew $350,000—everything he had and then some—on his defense, a setback that nearly closed his law practice.

Patty Hearst’s 1976 bank robbery trial provided an opportunity for a comeback. The 200 reporters who descended upon San Francisco served as a powerful distraction from Bailey’s famous cramming. Newsweek reported on his “caviar and vodka suppers and nightly closings of San Francisco bars,” while author Shana Alexander wrote about the Bloody Marys and margaritas he’d drink at mid-trial lunches.

Following her conviction, Hearst lodged an unsuccessful appeal on the basis of ineffective counsel, later writing in her memoir that her lawyer regularly popped “hangover pills” and had delivered a bizarre, disjointed 45-minute summation with a flushed face and shaking hands. “I wondered if he had been drinking at lunch,” she wrote.

I wondered if he had been drinking at lunch. —Patty Hearst

“Absolutely not,” says Bailey. The next time he would be in so bright a spotlight was six years later, also in San Francisco, for his own drunk driving trial, at a time when he was, inconveniently, a pitchman for Smirnoff. Despite having refused blood alcohol tests and despite a parade of jailhouse cops who testified that he was acting drunk and belligerent, he got off with just a citation for running a stop sign, after his defense argued that it was in fact the arresting officer who had been drunk and belligerent.

His ingenious lawyer: Robert Shapiro.

Lee Bailey with his lawyers Al Johnson and Robert Shapiro arriving at San Francisco municipal court to defend against Bailey’s drunk driving charge. Getty Images

Bailey had befriended Shapiro while co-defending an accused cocaine smuggler in Hawaii in 1977, and they bonded so strongly that in 1980, when Shapiro’s first child, Brent, was born, he named Bailey (who has three sons himself) godfather.

For the Simpson case, in 1994, Shapiro, a well-known deal cutter, needed an experienced murder trial lawyer. Just before the trial, Shapiro watched helplessly as the power in the defense team shifted to Johnnie Cochran. Shapiro suspected that his old friend had joined the forces that were sidelining him, a struggle that came to a head when a scathing article about Shapiro’s ineptitude and ego appeared in the New York Daily News.

Some would call it indulgence, but I had a thoroughly good time.

Despite Bailey’s denials, Shapiro was convinced that he was behind the leak and declared war. “We can’t have snakes sleeping in the bed with us,” Shapiro told the Los Angeles Times. Shapiro refused to comment for this story, except to e-mail, “When he was in trouble in San Francisco and had his choice of any lawyer in the country, he chose me.” (Bailey now says Shapiro “had no talent in the courtroom.”) When Brent died of an accidental drug overdose in 2005, Bailey didn’t pick up the phone.

Three months before Simpson’s arrest in 1994, Shapiro brought Bailey into the case that would be his undoing. A French smuggler named Claude Duboc was sitting in a Tallahassee jail, accused of running a $165 million a year marijuana ring. After Shapiro dropped out of the case, Bailey inherited a client whose defense was so problematic that he had little choice but to cut a deal with the government.

David McGee, the U.S. attorney prosecuting the case, made it clear that the more of his ill-gotten fortune Duboc turned over to the government, the lighter his sentence would be. Behind closed doors, Bailey says he and McGee’s deputy hatched a plan. Bailey would sell the drug dealer’s two palatial French estates for the government. Bailey’s expenses and fees would come out of Duboc’s 602,000 shares of BioChem Pharma stock, which Duboc advised the government not to sell immediately, since the Canadian company was on the verge of developing a revolutionary AIDS treatment that would send the price soaring.

The government agreed not to sell and transferred the stock to Bailey’s Swiss bank account, warning him that if the stock tanked, there’d be no more money to pay him. Even if his fee had been negotiated as he claims, the details were never memorialized on paper.

Two years later Duboc fired Bailey, and the court ordered Bailey to return the stock, the value of which, true to Duboc’s prediction, had skyrocketed from just under $6 million to $26 million. Bailey flatly refused. “The deal I worked out was that I got this stock to cover fees,” Bailey tells me, reasoning that he had accepted a bet with a significant potential downside as well as an upside. He believes it became a problem only because the stock rose so precipitously. “The justice department stood to be mighty embarrassed if they had allowed a defense lawyer in a drug case to make a $25 million fee,” he says.

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“There’s not even a grain of truth in what he was saying,” McGee says. “He took money that was rightfully going to the government and that would have benefited his client.” The government produced a damning paper trail: Bailey had agreed that any fee he took would first be approved by the presiding judge, and early on he agreed to share a fee of $3 million, split among himself, Shapiro, and another attorney.

Shapiro showed up and testified that Bailey was making the whole fee structure up. Still, Bailey remained defiant in the face of the judge’s threats to jail him. “Hell, I’d do six months standing on my head for $10 million!” he told a reporter at the time.

It turned out that Bailey had already spent $3 million of the stock proceeds on a Florida house and a yacht restoration business. In March 1996, when he was unable to raise the $2.3 million it would take to access the stock for surrender, marshals tossed him into federal prison for contempt. After 44 days spent furiously trying to scrape together the money from friends, he walked out of jail flat broke, but 20 pounds heavier. “The food was so bad I ate a lot of junk food,” he says.

I decided I was going to live my life and let the candle burn, because you never know when it will get snuffed out.

In 1998, while he was feverishly working cases to pay his debtors, Patty, his wife and partner of 25 years, a woman he says he’d “no doubt” still be with today, was diagnosed with terminal pancreatic cancer. Minutes before Bailey was due to deliver a summation on a case in North Carolina, he received a call informing him that she might not survive the night.

“Lee goes out and gives his closing argument. You could hear a pin drop,” says his friend and longtime investigator Patrick McKenna. “I have no idea how he did it. The jury was out 13 minutes before they acquitted.” At the hotel afterward, Bailey collapsed in McKenna’s arms. “In all the years I’d known him I’d never seen him like that,” McKenna says.

Today Bailey—pictured here in 2016 with his dog Brodie—operates an advisory business out of an office above a Yarmouth, Maine, beauty salon. Getty Images

Barely a week after Patty’s death, Bailey learned that Florida intended to disbar him over the Duboc business. In 2003, Massachusetts followed suit. Lacking the funds to hire a lawyer, Bailey represented himself in tax court in 2012 to contest the IRS’s demand for more than $4 million in unpaid taxes.

The IRS was doubtful that his Chris-Craft yacht, Spellbound, was a bona fide charter business, but Bailey informed the agency that sailing was pure drudgery. “It’s no fun to drive a boat,” Bailey testified, pointing out that the Spellbound’s steering and navigation controls were far removed from the revelers on the deck below. For his efforts, the court sliced his tax bill in half.

Bailey’s last stand came in a Portland, Maine, courtroom in March 2013. The year before, the Board of Examiners narrowly voted (five to four) to deny him entry to the bar, citing “Bailey’s word-smithing and hair-splitting rather than admitting mistakes.” He appealed and marched 18 character witnesses through court to testify to his deep contrition. “Duboc was an aberration,” his former partner Kenneth Fishman testified, “not indicative of the man or attorney that he is.”

Bailey was the last witness to appear before Justice Donald Alexander, and he had been prepped by his attorney to throw himself on the mercy of his inquisitor. Thomas Knowlton, an assistant attorney general, provided him the opportunity.

“So you would agree, Mr. Bailey, that you misappropriated roughly $3 million?” Knowlton asked. “No, sir,” Bailey responded. “Because misappropriated is a word used in criminal law, which is the equivalent of larceny, and that takes an intent.” Knowlton regrouped, gave the legend another shot. “At the end of the day, Mr. Bailey, it’s fair to say that you spent $3 million that didn’t belong to you?” Bailey responded, “I spent $3 million that has been adjudged was not mine. At the time I spent it, I had a reasonable belief that it was mine.”

Alexander ruled in Bailey’s favor, but in April of the following year the Maine Supreme Judicial Court reversed the ruling and voted four to three against the famed attorney. “Bailey,” it wrote, “minimizes the wrongfulness and seriousness of the misconduct for which he was disbarred.”

That mea culpa shit wasn’t going to work with Lee. He wasn’t about to give those snotty little government guys any quarter.

Bailey’s intractability wasn’t a surprise to his friends. “That mea culpa shit wasn’t going to work with Lee,” McKenna says. “He wasn’t about to give those snotty little government guys any quarter.”

As heartbreaking as his friends consider his career finale to be, Bailey is remarkably unfazed. “I won’t say it’s depressing, because I don’t think I ever get depressed,” he says, leaning back in a leather chair in his snug garret above the salon, amid scale models of the airplanes he once owned and a big framed print of himself and Cochran flanking Simpson at the moment the not-guilty verdict was read.

His life is pretty mundane now: Jeopardy to keep his faculties sharp, and the occasional aerobics class to work off the Canadian Club. “I had a Lear jet at age 33, while I was still young enough to enjoy it,” he says. “I’d probably be a very secure 83-year-old had I not had 52 airplanes and about 25 boats. But I decided I was going to live my life and let the candle burn, because you never know when it will get snuffed out. Some would call it indulgence, but I had a thoroughly good time."

This story appeared in the August 2017 issue of Town & Country.

