Pretty Boy Floyd

His spree of murders and robberies continued, and after gangster John Dillinger was shot to death in an FBI ambush in Chicago in 1934, Floyd was named "Public Enemy #1. " Although there was a $25,000 reward for his capture, Floyd was considered a hero in his area of Oklahoma, one reason being that whenever he returned there he would use some of the loot from his previous robberies to buy food and clothes for many of the poverty-stricken residents of the Cookson Hills, where he grew up. Also, whenever he robbed banks in the area, the first thing he did was tear up all the mortgages he could find, an act that endeared him to many of the local residents who were on the verge of losing their homes, farms and businesses to the banks. Floyd's career was coming to a close, though.

His name and that of fellow professional triggerman Adam Richetti surfaced during the investigation into the infamous "Kansas City Massacre" of June 17, 1933, in which five men, including an FBI agent and several local police officers, were killed during an attempt to free a gang leader being transported to prison, although Floyd always denied being involved. One theory, however, was that it wasn't an attempt to free the hood, a small-timer named Frank Nash--who was one of those killed--but an assassination ordered by Nash's associates, who were afraid he'd rat them out in exchange for a release from prison or a reduced sentence. The theory was given credence by the fact that both Floyd and Richetti didn't belong to any particular gang and had no real ties to Kansas City, but were well known as killers for hire.

According to his only living son, Dempsey, Floyd loved the movie Dracula (1931) with Bela Lugosi.

Oklahoma folk legend Woody Guthrie wrote and recorded "The Ballad of Pretty Boy Floyd". It became on of his most popular songs during the 1930s. The song was later covered by Bob Dylan and The Byrds, among others.

One of seven children of dirt-poor Georgia farmers, Charles Arthur Floyd was born on February 3, 1904. His family moved to Oklahoma shortly after his birth, where they bought a small farm. Their luck was no better in Oklahoma than it was in Georgia, and drought, plagues of insects and devastating dust storms combined to keep them just barely out of the poorhouse. When Floyd was 16 he married, had a son and left the farm looking for work, but was unable to find any. Desperate to keep his family fed, he got hold of a gun and robbed a post office, netting $350 in pennies. He was soon arrested for the crime, but his father managed to get him out of trouble. Charles, however, liked the idea of being able to score such "easy money" and he and his wife headed to St. Louis, Missouri, where he figured the pickings were better than they were in rural Oklahoma. He robbed a grocery store and got more than $16,000. The money didn't last long, however, as he was soon arrested by local police who became suspicious of someone who had no job and no means of support driving a brand-new car and wearing expensive clothes. They searched the car and found money from the grocery store robbery, some of it still wrapped in paper with the store's name on it. He was sentenced to five years in state prison, during which time his wife gave birth to a son and divorced him. Released after having served three years, Floyd vowed that he would die before going back to prison again. He went back home to Oklahoma and discovered that his father had been killed in an argument with a local man, who was tried for the crime but acquitted. Soon afterward the man disappeared and was never seen again. Floyd, who had told several people that he would kill the man the first chance he got, was suspected of murdering him, but there was no evidence and he was never charged. He soon moved to East Liverpool, Ohio, which was a haven for bootleggers and liquor smugglers. He hired himself out as an enforcer for many of the gangs that operated in the area and gained a reputation as a cold, efficient killer. Heading to Kansas City, he hooked up with one of the criminal gangs that infested the area at the time, many of which were under the protection of the corrupt Pendergast political machine. It was there that he picked up the two things that would make him one of the era's most famous criminals: his skill with a machine gun and the nickname "Pretty Boy," given to him by a prostitute who was enamored of him. He hated the name, but it stuck and added to his reputation. Also adding to his reputation was his involvement in more than 30 bank robberies and ten murders. Floyd robbed so many banks in Oklahoma that bank insurance rates doubled. He was involved in a shootout with police in Bowling Green, Ohio, in which his accomplice and a police officer were killed and his girlfriend was shot and captured, but he managed to escape.