Harvey John Bailey (August 23, 1887 – March 1, 1979), called "The Dean of American Bank Robbers", had a long criminal career. He was one of the most successful bank robbers during the 1920s, walking off with over $1 million.
Born in West Virginia, Bailey robbed his first bank c. 1920 and his last in Kingfisher, Oklahoma, on September 9, 1933. He was incarcerated in the Kansas State Prison on July 8, 1932 until he escaped on June 1, 1933 during a breakout in which the warden was kidnapped and used as a human shield. He was recaptured and found guilty of complicity in the Urschel Kidnapping and was sentenced to life in prison on October 7, 1933. Originally sent to Leavenworth, he was transferred to Alcatraz on September 1, 1934. He was returned to Leavenworth in 1946 and transferred in 1960 to Seagoville Federal Correctional Institution in Texas, where he remained until he was released on March 30, 1964.
One of the many possible suspects listed as one of the four assassins in the St. Valentines Day Massacre is Fred "Killer" Burke. In his 1973 autobiography, however, Bailey insisted that he and Burke were planning a bank robbery together in Calumet City, Illinois, about 20 miles south of the massacre site, at the time the massacre took place.
Harvey Bailey died peacefully in Joplin, Missouri on March 1, 1979 at the age of 91.