ORLANDO, Fla. — For two generations, F. Lee Bailey has been America's most famous trial lawyer, a real-life Perry Mason who has defended some of the most notorious figures in recent memory: Sam Sheppard. The Boston Strangler. Patty Hearst. O.J. Simpson.
But now, in the twilight of his career, the 67-year-old Bailey finds himself in some of the worst legal trouble of his 40-year practice.
On Thursday, a federal judge in Orlando will hear arguments on whether to hold Bailey in contempt and send him to prison for refusing to turn over $2 million in legal fees that the government claimed for itself.
That comes weeks after a judge in a separate case recommended to the Florida Supreme Court that Bailey be disbarred for paying himself with millions in stock that the government intended to seize from a client.
Bailey's troubles have some colleagues wondering how the West Palm Beach-based lawyer's legendary career could be ending in such a mess.
"I'm surprised by all that. He has had a long and distinguished career," said Johnnie Cochran Jr., who along with Bailey was part of the Dream Team that won Simpson's acquittal on murder charges. "It's a tough time for him, and I think he deserves better."
Bailey's difficult year has also extended into his personal life.
His fourth wife, Patricia, and his mother died last year. And he testified in court last year — during an attempt to convince a judge that he cannot repay the $2 million — that he is broke.
It was Bailey who invented the modern celebrity lawyer in the 1960s and 1970s, when he was host of the TV show "Good Company" and wrote books such as "The Defense Never Rests."
Bailey's law career began in 1960 when he was admitted to the Massachusetts Bar after graduating with the highest grade point average in the history of Boston University's law school. He had previously dropped out of Harvard to serve as a Marine fighter pilot.
Bailey shot to fame in the 1960s defending in separate cases two doctors accused of killing their wives. He won an acquittal for George Elderly and won the reversal of a conviction for Sheppard in the celebrated case that inspired TV's "The Fugitive."
In 1971, Bailey won an acquittal for Ernest Medina, a soldier who was tried for his role in the My Lai massacre during the Vietnam War. He unsuccessfully defended Albert DeSalvo in the case of the Boston Strangler, who murdered 13 women.
Bailey's most visible defeat was the conviction of Patty Hearst, the newspaper heiress who was kidnapped by the Symbionese Liberation Army and took part in several bank robberies.
He is considered an expert on lie detector tests and aviation litigation and holds a commercial pilot's license.
But Bailey's abrasive — sometimes sneering — courtroom style and his penchant for attracting media attention have rubbed judges and other lawyers the wrong way. Bailey was censured by the Massachusetts Bar in 1970 for talking too much to the media and was barred in 1971 from practicing in New Jersey for one year for remarks he made on a case.
Some would argue that Bailey's latest problems are self-inflicted, the result of his efforts to secure legal fees.
In the Orlando case, a federal magistrate in January recommended that Bailey be found in contempt for taking $2 million from a Cayman Island bank account in 1998. The money had belonged to Bailey's former client William J. McCorkle, an informercial pitchman convicted of fraud, and was illegally earned and could be seized by the government, the magistrate said.
Bailey, in court papers, called the recommendation "heavily flawed in virtually every area of its long odyssey."
Last month, a judge in Naples recommended that Bailey be stripped of license to practice law in Florida after finding him guilty of misconduct and misappropriation. Bailey was accused of inappropriately using millions of dollars in stock belonging to a client, international drug trafficker Claude Duboc, to pay his own legal expenses. In 1996, he spent 43 days in jail for contempt of court stemming from the dispute.
Bailey did not return calls for comment, but his lawyer in the Orlando case, Richard Lubin, said: "He believes . . . that he hasn't violated the law or the ethics of the state of Florida."