Charles 'Pretty Boy' Floyd: The Depression-Era Robin Hood
By Sophia Maddox | May 24, 2024
All About Pretty Boy Floyd
Charles "Pretty Boy" Floyd was more than just a notorious bank robber; he was a symbol of rebellion and resilience during the tough times of the Great Depression. Known for his good looks and daring heists, Floyd's reputation went beyond that of a mere criminal. He became a folk hero to many, seen as a modern-day Robin Hood who redistributed wealth in a time of widespread poverty. With a flair for the dramatic and a knack for evading law enforcement, Floyd's story is a captivating mix of charm and danger. Explore the life of this infamous outlaw who walked the line between hero and villain, leaving an indelible mark on American history.
Mugshot of gangster Charles "Pretty Boy" Floyd.
One of the most colorful Depression-era criminals was the cherub-faced, Robin Hood–esque Charles "Pretty Boy" Floyd. Floyd's love for his machine gun and habit of robbing banks made him public enemy number one, but his fondness for destroying mortgages made him an outlaw hero of the 1930s. Here is the story of "Pretty Boy" Floyd, the "Robin Hood of the Cookson Hills."
The Young "Pretty Boy"
Floyd had a clean-shaven baby face. (Getty Images)
Charles Arthur Floyd was born in 1904 in Adairsville, Georgia, but his family moved to Oklahoma when he was still a boy. It was bad timing: The impoverished farming family, like many others, was about to experience the Dust Bowl, one of the biggest man-made environmental disasters of the 20th century. Floyd soon turned to whatever he could to make money, from the oil fields to armed robbery.
How He Became The Pretty Boy
Floyd may have earned his nickname working on the oil fields of Oklahoma. (pinterest.com)
Charles Floyd had another, less famous nickname as a teen and young man. During that time, he was called "Choc" because his favorite beverage was Choctaw beer. People began calling him "Pretty Boy" in his twenties, but it's not clear why. Some claim the nickname was given to him by a prostitute at his favorite brothel, but others attribute it to the nice clothes he insisted on wearing despite the filthy conditions of the oil fields. In yet another story, a witness to one of his robberies described him as a "pretty boy with apple cheeks." We may not know the true origin of the nickname, but we do know that Floyd hated it.
A Life Of Crime
St. Louis was one of the cities "Pretty Boy" Floyd targeted. (rootsandbloomsgarrison.blogspot.com)
Floyd was first arrested was when he was 18 years old after stealing $3.50 from his nearby post office. A few years later, he was caught robbing a St. Louis business and spent three and a half years in jail for it. When he was released, he upped the ante on his criminal activity, integrating himself within the Kansas City underworld and turning his larcenous attentions toward financial institutions. He was arrested several times for vagrancy and other petty crimes, but he often gave false names and quickly found himself back on the streets.
Cop Killer
Floyd was sentenced to serve at the Ohio State Penitentiary, but he escaped. (columbusnavigator.com)
On March 8, 1930, "Pretty Boy" Floyd was arrested for killing a police officer in Akron, Ohio during a botched robbery. He was sentenced to 12–15 years in the Ohio State Penitentiary, but he escaped without a trace. The next year, a pair of rum-running brothers were found murdered in their car in Kansas City, and Floyd was the chief suspect. He was also believed to be responsible for the murder of another policeman in another part of Ohio, a federal agent in Missouri, and a retired sheriff in Oklahoma.
"The Robin Hood Of Cookson Hills"
Floyd was compared to Robin Hood because he took from the rich to give to the poor. (thedissolve.com)
When the Dust Bowl struck and the stock market crashed, many of the families in rural America were left destitute. Floyd's own family had lived in extreme poverty, so he empathized all too well. According to legend, whenever he robbed a bank, he always took a moment to destroy the bank's mortgage documents. At that time, the paper documents housed at the banks were the only proof that these mortgages existed; once the papers were destroyed, the mortgage was null and void. This endeared him to many of those struggling to survive the Great Depression, who began calling him "the Robin Hood of Cookson Hills," a mountainous extension of the Ozarks in Oklahoma.
The Kansas City Massacre
Floyd claimed he wasn't involved in the Kansas City Massacre, but the FBI was sure he was. (kchistory.org)
In 1933, Floyd and two accomplices plotted to intercept the delivery of his associate Frank Nash to a Kansas prison, assisting him to escape. The trio hid out at the Union Railway Station in Kansas City and fired on the guards transporting Nash, killing an FBI agent, a police chief, and two patrolmen as well Nash before beating a hasty retreat. At least, that's the story the FBI told. Floyd insisted that he wasn't involved in the Kansas City Massacre, and historians have uncovered compelling evidence to support his claim over the years. However, the FBI was certain of Floyd's participation, and they were determined to track him down.
The Second Public Enemy Number One
John Dillinger was the FBI's first "public enemy number one." (rollingstone.com)
John Dillinger, the first man declared "public enemy number one" by the FBI, was gunned down in 1934. After his death, Floyd moved up to claim the federal title, and a bounty of $23,000 was place on his head. During this time, Floyd laid low for a year or so, living under the name "George Sanders."
Death Of A Pretty Boy
On October 22, 1934, Floyd was spotted outside East Liverpool, Ohio. As the FBI and local law enforcement closed in, Floyd and his companion fled into a cornfield. Shots rang out, and at least two struck Floyd. According to the official report from the FBI, Floyd's final words were "I'm done for. You've hit me twice." Although the FBI claimed credit for gunning down Floyd, some members of the local law enforcement later stated that it was the local police that shot "Pretty Boy" Floyd.
