Oklahoma Outlaws | Pretty Boy Floyd

One of the most well-known bank robbers in United States history, Pretty Boy Floyd, had strong ties to Oklahoma. Charles Floyd was born in Georgia in 1904, as one of many children, his family soon moved to Akins, Okla., to start a farm in the Cookson Hills where they lived an extremely impoverished life. Tired of living in poverty, Floyd soon turned to crime, and was first arrested for petty theft at the young age of 18.

At 20 years old, Floyd married Ruby Hardgraves, and they eventually had a son named Charles. Shortly after the pair were married, Floyd graduated to serious theft and was sentenced to five years for robbing a payroll delivery vehicle in St. Louis. Hardgraves divorced Floyd during his imprisonment, although the two reconnected later in life.

After his release, Floyd drifted north towards Kansas City, quickly getting involved with the city’s criminal underworld. At the time, his specialty was highway robbery. He and his accomplices would stop cars, and with the victims at gunpoint, demand all the valuables on board. Between 1929 and 1930, he was arrested multiple times on suspicion of armed robbery, but the police could never find anything conclusive.

It was somewhere around this time that he picked up the moniker “Pretty Boy,” and rumors abound about its origin. Some reports say he got his nickname from a prostitute girlfriend, while others credit co-workers on an oil rig who mocked his clothing. Some documentaries note that he got his name early on in his criminal career when he was described as “A pretty boy with apple cheeks.” Regardless, it’s known he hated the name.

Floyd was known for his reckless use of a machine gun that he welded. Around 1929 he honed the talent he is best known for: bank robbery. His flair for the dramatic and the police’s inability to catch him made him a media sensation.

He began robbing banks in Ohio with other gangsters, and soon moved on to other territories. It is told that bank insurance rates in Oklahoma doubled, although this has not been verified. He became popular with the public by allegedly destroying mortgage papers at many of the banks he robbed, liberating many debt-ridden citizens. Again, these acts were never fully verified. Known for sharing money he’d stolen, he was often protected by the locals, and was dubbed the “Robin Hood of Cookson Hills.”

Floyd is credited with no fewer than 50 bank robberies during 1931 alone, including a bank in Sallisaw, Okla., while his friends and family members watched on.

One of the more memorable events Floyd was accused of taking part in – which he denied – was the Kansas City Massacre in June of 1933. It was reported that he and two accomplices attempted to prevent fellow criminal Frank Nash from being returned to prison. A shootout ensued, and Nash, two officers, a police chief, and an FBI agent were killed.

After the death of John Dillinger, Floyd was declared “Public Enemy No. 1” and a $23,000 bounty was offered for his capture – dead or alive. He evaded capture for more than a year, until he was discovered outside of Wellsville, Ohio. He made his escape, but was later found in an East Liverpool cornfield. Floyd was shot twice in the deadly shootout on October 22, 1934. He was killed by FBI Agent Melvin Purvis, who became famous after taking out Dillinger.

Following his death, Pretty Boy Floyd’s body was returned to the lush Cookson Hills of his youth. He’s buried in the Akins Cemetery in Sequoyah County. It was written that a year before his death, while at the Akins Cemetery in Sallisaw, Floyd had told his mother, “Right here is where you can put me. I expect to go down soon with lead in me. Maybe the sooner the better. Bury me deep.”

Floyd has been portrayed in movies, songs, books, and biographies, including Woody Guthrie’s song “Pretty Boy Floyd,” which recounted Floyd’s supposed generosity to the poor. It satirically compared foreclosing bankers to outlaws.

Several movies have been made about Floyd:Pretty Boy Floyd (1960);A Bullet for Pretty Boy (1970); The Story of Pretty Boy Floyd (1974); The Kansas City Massacre (1975); and Public Enemies (2009), where he is falsely depicted as being killed before John Dillinger.