F. Lee Bailey, the theatrical criminal lawyer who invited juries into the twilight zone of reasonable doubt in defense of Patricia Hearst, O.J. Simpson, the Boston Strangler, the army commander at the My Lai Massacre in Vietnam and other notorious cases, died on Thursday June 3 2021 in Atlanta. He was 87. His son Bendrix confirmed the death, in hospice care, but did not specify the cause. He said his father had been in poor health in recent years and living in Georgia to be near another son, Scott. In recent years he had been running a business consultancy out of an apartment above a Yarmouth hair salon owned by his girlfriend. Francis Lee Bailey was born on June 10, 1933, in Waltham, Mass., the oldest of three children of an advertising salesman and a nursery-school teacher, Grace Bailey Mitchell. He graduated in 1950 from Kimball Union Academy, in Meriden, N.H., and enrolled in Harvard but dropped out after two years to join the Navy. He transferred to the Marines and became a fighter pilot and an officer representing servicemen in courts-martial, although he had no legal training. Discharged in 1956, he enrolled at Boston University Law School, which, because of his experience, waived entrance requirements. He was class valedictorian at graduation in 1960. During law school, he founded a private detective agency, helping lawyers with cases. He sold it later but retained its services for his Boston firm. In 1960, he married Florence Gott. They had two sons, Bendrix and Brian. After a divorce, he married Froma Portney and had another son, Scott. After a 1972 divorce, he married Lynda Hart. They were divorced in 1980. In 1985, he married Patricia Shiers, who died in 1999. In addition to his sons, Mr. Bailey is survived by a sister, Nancy Bailey; and five grandchildren. Mr. Bailey, who often carried a snub-nosed revolver in a shoulder holster, was an avid yachtsman and pilot, flying his jet around the country to cases and meetings. He owned a helicopter-manufacturing business in Michigan, and in 1968 helped found the Professional Air Traffic Controllers Organization, the union President Ronald Reagan broke after a strike in 1981. He represented families of passengers killed when a Soviet warplane shot down Korean Airlines 007 in 1983 and in the bombing of Pan Am 103 over Lockerbie, Scotland, in 1988. He failed to keep Patty Hearst, the kidnapped publishing heiress, out of prison for her role in a bank robbery. He fell short in his insanity defense of the confessed Boston Strangler, Albert DeSalvo, and could not save himself from contempt of court citations, humiliating handcuffs and disbarment in 2001 for misappropriating millions. Mr. Bailey gained national attention in 1966, when he succeeded in reversing the murder conviction of Dr. Sam Sheppard, the Ohio osteopath whose case inspired the television series and movie “The Fugitive.” Dr. Sheppard had been convicted in 1954 of bludgeoning his wife but steadfastly claimed that he had been knocked out in a struggle with the killer after he returned home to discover the body. The reversal by the United States Supreme Court, on grounds that jurors had been unfairly exposed to sensational publicity, led to a second trial in which Mr. Bailey cast new light on the evidence, discredited a key prosecution witness and delivered a masterful closing. Dr. Sheppard was acquitted, and Mr. Bailey was hailed in The New York Times as “easily the shiniest new star in the criminal law field.” Soon after the Sheppard case, Mr. Bailey was called to Bridgewater State Hospital in Massachusetts, which housed sex offenders and the criminally insane. Albert DeSalvo, an inmate, told Mr. Bailey that he was the Boston Strangler who had raped and slain 13 women from 1962 to 1964, supposedly providing details only the killer could know. Mr. DeSalvo, facing unrelated rape and assault charges, was not yet suspected in the killings, and Mr. Bailey agreed to represent him. At the 1967 trial, he took a risk and raised the confession, trying to show that his client was insane, but a judge ruled it inadmissible, and Mr. DeSalvo was convicted, found sane and sentenced to life in prison. In 1971, Mr. Bailey defended Capt. Ernest L. Medina in a court-martial over one of the Vietnam War’s most notorious atrocities, the 1968 massacre of 104 South Vietnamese villagers in what had become a flash point in the antiwar movement. The captain was charged with killing a woman and allowing his men to slaughter villagers. Mr. Bailey said that his client had shot the woman in an “instinctive battlefield reaction,” and that he had not known that his troops were out of control until it was too late. The captain was acquitted. Of 26 men charged in the massacre, only Lt. William Calley, a platoon leader, was convicted of murder. (Lieutenant Calley ultimately served slightly more than three years of house arrest and barracks confinement.) In the 1976 case of Ms. Hearst, who had been photographed with her Symbionese Liberation Army captors in a 1974 San Francisco bank robbery, Mr. Bailey argued that she had been brainwashed and had gone along to save her life. He called 71 witnesses, including Ms. Hearst, but she was convicted and went to prison for 22 months. She sued Mr. Bailey for incompetent representation, but dropped the suit after President Jimmy Carter commuted her term. In 1995, Mr. Bailey was part of the “dream team” of lawyers — Johnnie L. Cochran Jr., Alan M. Dershowitz, Barry Scheck and Robert L. Shapiro — who defended the former football star O.J. Simpson against charges that he had killed his former wife, Nicole, and her friend Ronald L. Goldman in a ferocious knife attack. The prosecution case seemed overwhelming, but Mr. Bailey’s cross-examination of Detective Mark Fuhrman was widely considered a key to acquittal. The Massachusetts bar once censured Mr. Bailey for self-promotion, and New Jersey banned him from state courts for a year for contempt. But his worst trouble arose in Florida in 1996. He was held in contempt for refusing to surrender fees taken for defending a drug trafficker and stock left with him in escrow by his imprisoned client. A federal court said the trafficker had forfeited all his assets in a 1994 plea deal, and demanded that Mr. Bailey give them up. He refused. But after 43 days in jail, he surrendered stock worth millions and his yacht and was released. In 2001, Florida’s Supreme Court disbarred him for misappropriating the stock, and Massachusetts disbarred him reciprocally in 2003. In 2013, Mr. Bailey’s request to practice law in Maine, where he had a home, was denied by the state. In 2016, Mr. Bailey filed for bankruptcy in Maine, saying he owed more than $5 million in taxes and had minimal assets, including a condo in Yarmouth, Me., with a $365,000 mortgage.