Violent Minds

Charles “Pretty Boy” Floyd

Introduction

Charles Arthur “Pretty Boy” Floyd was one of America’s most notorious bank robbers during the Great Depression era, whose criminal career spanned from the mid-1920s until his violent death in 1934. Born into poverty in rural Georgia and raised in Oklahoma, Floyd became a legendary outlaw whose exploits captivated the American public while terrorizing law enforcement across the Midwest.

Early Life and Criminal Origins

Charles Arthur Floyd was born on February 3, 1904, in Adairsville, Georgia, to Walter Lee Floyd and Mamie Helene Echols. In 1911, his family relocated to Akins, Oklahoma, where Floyd grew up in the hardscrabble environment of the Cookson Hills. Drawn into crime by poverty and limited opportunities, Floyd began his criminal career early, stealing $3.50 from a local post office at age 18.

Floyd’s first major crime occurred in 1925 when he participated in a payroll robbery in St. Louis, Missouri, for which he was sentenced to five years in prison. He served three and a half years before being granted parole, emerging from the Missouri State Penitentiary with hardened criminal connections that would shape his future.

Acquisition of the “Pretty Boy” Nickname

The origin of Floyd’s infamous nickname remains disputed, with multiple accounts explaining how he became known as “Pretty Boy“. One version suggests a payroll master in the 1925 St. Louis robbery described one of the robbers as “a pretty boy with apple cheeks“. Another account claims it originated from his habit of wearing clean white dress shirts to work in the oil fields. Regardless of its origin, Floyd despised the nickname, preferring to be called “Choc” or simply “Charles“.

Criminal Career and Bank Robberies

Following his release from prison in 1929, Floyd embarked on a prolific criminal career that would make him one of the most wanted men in America. Between 1929 and 1934, Floyd robbed approximately 30 banks across the Midwest, primarily targeting financial institutions in Ohio and Oklahoma. His criminal activities were so extensive that bank insurance rates in Oklahoma doubled during his peak period of activity.

Floyd’s modus operandi typically involved the brazen use of machine guns and bulletproof vests, often working alone or with a small group of accomplices. He rarely concealed his identity during robberies, frequently introducing himself to victims and bank officials. His criminal exploits gained widespread media attention, with newspapers attributing numerous crimes to him – many of which he likely did not commit.

Confirmed Murders and Violence

Floyd’s criminal career was marked by significant violence and confirmed killings. His confirmed murders included:

• Curtis C. Burke – A federal agent killed by Floyd on July 22, 1931, in Kansas City, Missouri
• Erv Kelley – A former sheriff of McIntosh County, Oklahoma, shot by Floyd on April 7, 1932, during a failed ambush attempt near Bixby, Oklahoma
• Patrolman R.H. Castner – Killed by members of Floyd’s gang on April 23, 1931, in Bowling Green, Ohio

Floyd was also suspected in the deaths of Kansas City brothers Wally and Boll Ash, rum-runners found dead in a burning car on March 25, 1931. According to FBI records and contemporary accounts, Floyd was suspected of killing as many as 10 people during his criminal career. Notably, Floyd carried a pocket watch with ten notches carved into it, allegedly representing the number of people he had killed.

The Kansas City Massacre Controversy

One of the most significant and controversial events associated with Floyd was the Kansas City Massacre on June 17, 1933. This incident involved an attempt to free prisoner Frank “Jelly” Nash during his transfer at Union Station in Kansas City, resulting in the deaths of four law enforcement officers and Nash himself. While J. Edgar Hoover and the FBI maintained that Floyd and accomplice Adam Richetti were involved, Floyd consistently denied participation in the massacre until his death.

Modern historians and evidence suggest Floyd may not have been involved in the Kansas City Massacre, with some attributing the killings to friendly fire and other gunmen. This incident, however, provided Hoover with the justification to intensify federal efforts to capture Floyd and expand FBI authority.

The Robin Hood Legend

Despite his violent criminal activities, Floyd developed a Robin Hood-like reputation among Depression-era Americans. He was dubbed the “Robin Hood of the Cookson Hills” by local Oklahoma residents who often protected him from law enforcement. This positive perception stemmed partly from unverified reports that Floyd destroyed mortgage documents during bank robberies, allegedly freeing debt-ridden citizens from their financial obligations. While never confirmed and likely mythical, this reputation endeared him to many struggling Americans during the Great Depression.

Death and Aftermath

After John Dillinger’s death in July 1934, J. Edgar Hoover declared Floyd “Public Enemy Number One“. Floyd’s criminal career came to an end on October 22, 1934, when he was cornered and killed by FBI agents led by Melvin Purvis in a cornfield near East Liverpool, Ohio. The circumstances of his death remain controversial, with conflicting accounts about whether he was executed after being wounded or killed during the initial confrontation.

Floyd’s funeral became the largest in Oklahoma history, with an estimated 20,000 to 40,000 people attending, demonstrating his enduring folk hero status among Depression-era Americans. His legacy continued in popular culture through Woody Guthrie’s protest song “Pretty Boy Floyd” and numerous films and books depicting his life.

Did You Know?

• Floyd’s share of his final bank robbery was only $120, demonstrating how little money he actually retained from his criminal activities.
• He was known to wear clean white dress shirts and maintained his appearance even while living as an outlaw, which may have contributed to his “Pretty Boy” nickname.
• Floyd had a distinctive tattoo called “Rose of No Man’s Land” on his shoulder, reportedly done by famous tattoo artist Bert Grimm in St. Louis.
• Despite his criminal reputation, Floyd maintained relationships with family and friends, even attending church services in Earlsboro while being actively hunted by law enforcement.

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