$1 for 3 months
$1 for 3 months

The short, violent life of a killer

The Examiner

Charlie Floyd was born in 1904 and grew up in Oklahoma. While growing up he idolized such trigger-happy outlaws as Jesse James and other legends of the Old West.

By his mid-teens, he began to emulate those outlaw heroes and soon made a name for himself as well. Charlie charmed all of the ladies within his circle of friends, but while still in his tender years, he turned that charm toward 16-year old Ruby Hargrove, and she married him in 1924. The birth of a baby boy, little Charles Dempsey Floyd Jr., quickly followed in that same year.

Ted Stillwell

Charlie worked hard to support his new family as a laborer but continued to charm the other women and entertained ideas of more remote regions and easier opportunities. Eventually, he left Ruby and the baby behind and embarked on a journey that would be dotted with crimes, actions that ultimately landed him in the penitentiary.

While making out a police report in one of his payroll robberies, a witness described the culprit as a “pretty boy with apple cheeks.” To Floyd’s considerable dismay, the press coverage stuck, and he carried the nickname “Pretty Boy Floyd” throughout the remainder of his life.

Pretty Boy Floyd turned to crime early and died young.

By the time Floyd was released from the pen in 1929, he learned that Ruby had filed for divorce, so Floyd found a new start, although not a new way of life. Floyd tied up with the criminal element in Kansas City – an association that would result in a 15-year sentence in the Ohio State Penitentiary. However, Floyd escaped while being transported to prison, and continued onward with a life of crime as a fugitive.

Over time, Floyd began to develop a profile as an enemy of the rich and a friend of the poor. The press referred to him as the “Phantom of the Ozarks” and the “Robin Hood of Oklahoma” for his acts of generosity toward ordinary citizens who had fallen on hard times during the Dust Bowl Days and the Depression. The public and especially Pretty Boy himself sure enjoyed the press coverage.

Meanwhile, Floyd tracked down Ruby and the kid, who were living in Kansas, and convinced her to leave her new husband and join him in hiding. They set up housekeeping under assumed names in Missouri, Arkansas and Oklahoma but were continually on the move because the law was always hot on their trail. Once again, he left his family behind for their own safety.

On June 17, 1933, while hanging around our neck of the woods, an incident in which four Missouri police officers were murdered sealed Floyd’s fate. This event, later known as the Kansas City Massacre or the Union Station Massacre, placed Pretty Boy Floyd high on the FBI’s most-wanted list. In his flight from justice, Floyd continued robbing and killing, and it is believed he even joined forces with fellow gangster John Dillinger for a while.

Pretty Boy Floyd met his death on October 22, 1934, when he was shot dead while resisting arrest in Ohio. They returned him to Oklahoma, where some 20,000 mourners attended his funeral.

The downtrodden public’s enthusiasm for Floyd’s life of crime ensured his place in American folklore by such ballads as “Pretty Boy Floyd” composed and performed by folk singer Woody Guthrie. Floyd also figured in John Steinbeck’s classic Depression era novel, “The Grapes of Wrath.”

Reference: "Encyclopedia off American Folklore," by Linda S. Watts.

To reach Ted W. Stillwell send e-mail to or call him at 816-896-3592