From Millionaire to Prisoner: How F. Lee Bailey Stole Millions in Drug Money and Lost Everything

The Fall of a Legal Titan

In the spring of 1996, one of America's most celebrated criminal defense attorneys found himself in an unfamiliar position: behind bars. F. Lee Bailey, the legendary lawyer who had freed accused murderers, defended heiresses, and stood beside O.J. Simpson in the trial of the century, was now wearing prison-issued clothing in a federal detention center. His crime? Refusing to surrender millions of dollars that did not belong to him.

The man who had once flown on private jets, lived in luxury, and commanded fees that could bankrupt small nations was now Inmate Bailey, locked in a cell for contempt of court. It was a stunning reversal of fortune, and it was only the beginning of a downward spiral that would end with Bailey disbarred, bankrupt, and working above a hair salon in Maine. By the time he died in 2021 at age 87, the once-mighty F. Lee Bailey owned little more than a gold Mercedes station wagon and a collection of model airplanes, reminders of the jets he used to own.

This is the story of how greed, arrogance, and a $20 million temptation destroyed one of the greatest legal careers in American history. It is a tale of betrayal, revenge, and the ultimate price of crossing the line between defending criminals and becoming one.

The Rise: A Legal Legend Is Born

Francis Lee Bailey Jr. was born in Waltham, Massachusetts, in 1933, the eldest son of an advertising man. At twenty, he left Harvard to join the military, where he flew Sabre Jets and developed a taste for speed, risk, and adrenaline, traits that would define both his legal career and his personal life. After leaving the military, Bailey attended Boston University Law School and quickly established himself as a courtroom prodigy.

His breakthrough came in the 1960s when he represented Dr. Sam Sheppard, a neurosurgeon convicted of brutally murdering his pregnant wife in a case that inspired the television series and film The Fugitive. Bailey secured Sheppard a new trial and won a not-guilty verdict, cementing his reputation as a lawyer who could achieve the impossible. He went on to defend Patty Hearst, the kidnapped newspaper heiress turned bank robber; Albert DeSalvo, the alleged "Boston Strangler"; and scores of other high-profile clients. For more about Bailey's legendary career and courtroom innovations, visit our F. Lee Bailey legal profile.

F. Lee Bailey in his later years

By the 1990s, Bailey was a household name. He was rich, famous, and seemingly untouchable. He owned private jets, lived in luxury, and even played himself in a movie. When O.J. Simpson was accused of murdering his ex-wife Nicole Brown Simpson and her friend Ronald Goldman, Bailey joined the "Dream Team" of defense attorneys. His cross-examination of Detective Mark Fuhrman, in which he exposed Fuhrman's history of racism and use of racial slurs, was a pivotal moment in Simpson's acquittal.

But behind the courtroom triumphs and the celebrity lifestyle, Bailey was about to make a decision that would destroy everything he had built. And it all began with a drug dealer named Claude Duboc.

The Claude Duboc Case: A Dangerous Client

In 1994, F. Lee Bailey and fellow attorney Robert Shapiro took on a new client: Claude Duboc, a wealthy marijuana smuggler and drug trafficker who had been arrested and extradited from Hong Kong. Duboc was facing life in federal prison on drug conspiracy and money laundering charges, and he needed the best legal representation money could buy.

As part of a plea bargain, Duboc agreed to forfeit his assets to the federal government. Among those assets was a block of 600,000 shares of BioChem Pharma, a Canadian pharmaceutical company, valued at approximately $5.89 million. The stock was trading at around $9 per share at the time.

But Duboc had a warning for the federal prosecutors in North Florida: Do not sell the stock immediately. BioChem Pharma, he explained, was developing a groundbreaking new AIDS drug, and the stock was about to skyrocket in value. If the prosecutors seized the stock, they would be required by policy to sell it right away, potentially costing the government millions in future profits.

The prosecutors faced a dilemma. They wanted to maximize the value of Duboc's forfeited assets, but they also needed to follow protocol. So they made a deal with Bailey: he would hold the stock temporarily on behalf of the government until it could be properly liquidated. Bailey agreed, and the $5.89 million in BioChem Pharma stock was deposited into his account at Credit Suisse in Geneva, Switzerland.

It seemed like a reasonable arrangement. Bailey was a respected attorney, an officer of the court, and a man of integrity. What could possibly go wrong?

The $20 Million Temptation: When Greed Takes Over

The $20 million in BioChem Pharma stock that Bailey claimed as his own

Claude Duboc was right. BioChem Pharma's stock exploded in value. Within two years, the shares that had been worth $5.89 million were now worth over $20 million. The stock had gone from $9 per share to over $50 per share, and Bailey was sitting on a fortune that did not belong to him.

And then Bailey made a decision that would change his life forever: he decided the money was his to keep.

Bailey's argument was audacious. He claimed that the stock had not been given to him as a trustee or a custodian, but as payment for his legal fees. He said the stock had been transferred to him "in fee simple," a legal term meaning he owned it outright. In other words, the $20 million windfall was not the government's money, it was his.

There was just one problem: Bailey had never disclosed this arrangement to the government. He had never paid income tax on the $20 million gain. And he had already started spending the money.

According to court documents, from the time Bailey received the stock through the end of 1995, the BioChem Pharma profits represented a staggering 80 percent of his gross income. He spent approximately $3.5 million on personal expenses, maintaining his lavish lifestyle of private jets, luxury homes, and expensive tastes. He continued to live like a millionaire because, in his mind, he was one.

But the federal prosecutors in Florida saw things very differently. They had entrusted Bailey with the stock on the understanding that it belonged to the government, not to him. When they learned that Bailey had spent millions of dollars and was now claiming the entire fortune as his own, they were furious.

The government filed an emergency motion, and Judge Maurice Paul ordered Bailey to appear at a hearing in Ocala, Florida, on February 2, 1996. The judge's instructions were clear: bring the stock with you.

Bailey showed up. But he came empty-handed.

Robert Shapiro's Revenge: A Courtroom Betrayal

The hearing in Ocala was supposed to be a routine matter, a chance for Bailey to explain his position and work out an arrangement with the government. But when Bailey walked into the courtroom that morning, he saw something that made his blood run cold: Robert Shapiro, his former colleague from the O.J. Simpson trial, sitting in the gallery with a smirk on his face.

Shapiro was there to testify, for the government.

The relationship between Bailey and Shapiro had soured during the Simpson trial. Shapiro, who had originally assembled the Dream Team, felt that Bailey and Johnnie Cochran had pushed him aside and taken credit for the acquittal. He resented Bailey's aggressive tactics, his willingness to play the "race card," and his larger-than-life personality. The two men had barely spoken since the trial ended.

Now, Shapiro had his chance for revenge.

Shapiro's testimony was devastating. He contradicted Bailey's claims at every turn, telling the court that the stock had always been understood to belong to the government, not to Bailey. He said Bailey had been acting as a custodian, not an owner. And he made it clear that Bailey's decision to spend the money was not only unethical, it was theft.

Bailey later recalled the moment he saw Shapiro in the courtroom. "He was smirking at me," Bailey said. "I knew just what Shapiro was thinking: 'I got you back, you son of a bitch!'"

Judge Paul was not amused by Bailey's refusal to turn over the stock. He had ordered Bailey to bring the money to court, and Bailey had defied him. The judge's ruling was swift and severe: F. Lee Bailey was in contempt of court.

On March 6, 1996, Bailey was sent to the Federal Detention Center. He would spend the next six weeks behind bars.

Six Weeks in Federal Prison: The Unthinkable Happens

For a man who had spent his entire career defending accused criminals, the experience of being incarcerated was surreal. Bailey, who had walked countless clients out of courtrooms as free men, was now wearing a prison uniform and sleeping in a cell. He was 62 years old, and he was a federal prisoner.

The media had a field day. Headlines screamed about the fallen legal titan, the man who had defended O.J. Simpson and now found himself on the wrong side of the law. Bailey's reputation, built over decades of courtroom victories, was crumbling.

But Bailey refused to back down. Even from his jail cell, he insisted that the money was rightfully his. He claimed that the government was persecuting him, that he was being punished for his role in the Simpson trial, and that the entire case was a vendetta.

Finally, on April 20, 1996, Bailey was released from jail. He had been given an ultimatum: turn over the stock within one year, or face further legal consequences. Bailey, realizing that he had no choice, eventually surrendered the stock to the government.

But the damage was done. Bailey had spent $3.5 million that did not belong to him. He had defied a federal judge. And he had lied under oath about the nature of the stock arrangement. The legal establishment was not going to forgive him.

The Disbarment: A Career Destroyed

The Florida Bar launched an investigation into Bailey's conduct in the Duboc case. The findings were damning. Bailey had mishandled client funds, spent money that belonged to the government, and offered false testimony in court. In 2001, the Florida Supreme Court issued its ruling: F. Lee Bailey was disbarred.

The court's decision was scathing. It cited "multiple counts of egregious misconduct, including offering false testimony" and found that Bailey had violated the most basic ethical obligations of an attorney. The disbarment was not temporary, it was permanent.

In 2003, Massachusetts followed suit. Under reciprocal discipline rules, Bailey was automatically disbarred in his home state as well. The man who had once been one of the most sought-after defense attorneys in America was now unable to practice law anywhere.

Bailey tried to fight back. He appealed the disbarment, arguing that he had been unfairly targeted and that the punishment was disproportionate to his alleged misconduct. But the courts were unmoved. Bailey's career as a lawyer was over.

In 2014, Bailey made one last attempt to return to the courtroom. He passed the Maine bar exam and applied for admission to practice law in the state. But the Maine Supreme Court issued a 59-page decision denying his application. Legal experts compared the rejection to "throwing LeBron out of the NBA", it was an unprecedented rebuke of one of the greatest legal minds of his generation.

Bailey would never practice law again.

The Financial Collapse: From Private Jets to Bankruptcy

The disbarment was only the beginning of Bailey's financial ruin. Without the ability to practice law, his income dried up. The IRS came after him for unpaid taxes on the BioChem Pharma stock profits, over $5 million in back taxes and penalties. Bailey had never paid income tax on the $20 million gain because he had claimed it was not income, but a return of assets. The IRS disagreed.

Bailey's fortune evaporated. The private jets were sold. The luxury homes were gone. The lavish lifestyle that had defined his career was over. In 2016, at the age of 83, F. Lee Bailey filed for bankruptcy in Maine.

His listed assets were heartbreaking: a 1999 Mercedes station wagon (gold, of course) and a few personal belongings. He owed the IRS over $5 million, and he had no way to pay it. Bankruptcy, he hoped, would allow him to discharge the debt and start over. But tax debts are notoriously difficult to discharge in bankruptcy, and Bailey's hopes were largely in vain.

Meanwhile, in 2005, the federal government and Florida law enforcement agencies split $11 million from the sale of Claude Duboc's forfeited assets. Bailey received nothing. Duboc, the drug dealer whose stock had caused Bailey's downfall, was serving a life sentence in federal prison.

The Final Years: Living Above a Hair Salon

By 2017, F. Lee Bailey was living in Yarmouth, Maine, with his girlfriend, Debbie Elliot, a hairstylist. He worked as a "consultant" in an office above her salon. The office was decorated with models of the private jets he used to own, a painful reminder of the life he had lost.

In an interview with Town & Country magazine, Bailey tried to put on a brave face. "I won't say it's depressing, because I don't think I ever get depressed," he said. But the reality was undeniable: one of the greatest lawyers in American history was broke, disbarred, and forgotten.

Bailey still believed that O.J. Simpson was innocent. He still believed that he had been unfairly targeted by prosecutors who resented his role in the Simpson trial. And he still believed that the BioChem Pharma stock had been his to keep.

Alan Dershowitz, Bailey's former colleague, believed that Bailey's downfall was at least partially motivated by revenge. "Without a doubt," Dershowitz told Town & Country. "I think it was a major factor in the vindictive way in which he's been treated."

Bailey himself agreed. "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,'" Bailey said. "They blamed me for O.J. walking free."

But whether or not the disbarment was motivated by the Simpson trial, one thing was clear: Bailey had crossed a line. He had taken money that did not belong to him, spent it on himself, and lied about it under oath. And he had paid the ultimate price.

Bailey tried to stay in touch with O.J. Simpson after Simpson was convicted in a Nevada robbery case and sent to prison. But eventually, the calls stopped. Bailey later learned that Simpson had been warned by prison officials to stay away from Bailey if he wanted to get on the good side of the parole board.

Even O.J. Simpson, the man Bailey had helped set free, wanted nothing to do with him.

The End: Death of a Legend

On June 3, 2021, F. Lee Bailey died in hospice care in Georgia. He was 87 years old. He had been married four times, divorced three times, and had three children. He died essentially penniless, his fortune gone, his reputation destroyed, and his law license revoked.

The obituaries were respectful but honest. They chronicled his legendary career, the Sam Sheppard case, the Patty Hearst trial, the O.J. Simpson acquittal, but they also detailed his spectacular fall. The BioChem Pharma scandal, the disbarment, the bankruptcy, and the final years living above a hair salon in Maine.

Bailey's story is a cautionary tale about the dangers of greed and the consequences of crossing ethical lines. He was a brilliant lawyer, a courtroom genius, and a man who could have retired as one of the greatest legal minds of his generation. Instead, he will be remembered as the lawyer who stole $20 million in drug money and lost everything.

For those interested in exploring more about legendary defense attorneys and their complex legacies, we encourage you to visit our Advocacy Legends page, where we examine the careers of figures like Leslie Abramson and Geoffrey Fieger. These attorneys, like Bailey, pushed the boundaries of legal defense and left lasting impacts on the American justice system.

If you have thoughts on F. Lee Bailey's legacy or the ethics of criminal defense, we invite you to share them on our Contact Page. And for more in-depth analyses of famous legal cases and controversial attorneys, visit our homepage.

Conclusion: A Legacy Tarnished Forever

F. Lee Bailey's life is a study in contradictions. He was a man who defended the accused and championed the presumption of innocence, yet he stole millions of dollars and lied under oath. He was a brilliant legal strategist who could outwit prosecutors and sway juries, yet he made the catastrophically stupid decision to spend money that did not belong to him. He was a legend who ended his life in disgrace.

The BioChem Pharma scandal did not just cost Bailey his law license, it cost him his legacy. Today, when people remember F. Lee Bailey, they do not think of Sam Sheppard or the O.J. Simpson trial. They think of the lawyer who stole drug money and ended up broke and disbarred.

Bailey's fall from grace is a reminder that no one is above the law, not even the lawyers who defend those accused of breaking it. It is a reminder that greed can corrupt even the most brilliant minds, and that the consequences of unethical behavior can be swift and merciless.

In the end, F. Lee Bailey got what so many of his clients avoided: justice.

References

1. Silverman, Ira, and Fredric Dannen. "A Complicated Life." The New Yorker, March 11, 1996. Available at: https://www.newyorker.com/magazine/1996/03/11/a-complicated-life
2. "F. Lee Bailey Disbarred In Florida." CBS News, November 21, 2001. Available at: https://www.cbsnews.com/news/f-lee-bailey-disbarred-in-florida/
3. "F. Lee Bailey Freed From Jail In Dispute Over Drug Money." The New York Times, April 20, 1996. Available at: https://www.nytimes.com/1996/04/20/us/f-lee-bailey-freed-from-jail-in-dispute-over-drug-money.html
4. Rosenwald, Michael S. "O.J.'s last defender - F. Lee Bailey - is broke, disbarred and working above a hair salon." The Florida Times-Union, July 21, 2017. Available at: https://www.jacksonville.com/story/news/nation-world/2017/07/21/oj-s-last-defender-f-lee-bailey-broke-disbarred-and-working-above-hair/15765639007/
5. "F. Lee Bailey, Lawyer for Patty Hearst and O.J. Simpson, Dies at 87." The New York Times, June 3, 2021. Available at: https://www.nytimes.com/2021/06/03/us/f-lee-bailey-dead.html
6. F. Lee Bailey. Wikipedia. Available at: https://en.wikipedia.org/wiki/F._Lee_Bailey
7. "Law enforcement splits $11 million taken from drug dealer." Sarasota Herald-Tribune, June 24, 2005. Available at: https://www.heraldtribune.com/story/news/2005/06/24/law-enforcement-splits-11-million-taken-from-drug-dealer/28851013007/