Charles 'Pretty Boy' Floyd | Biography

• By Stone Palmer
• Original : February 02, 2025

Who is Charles "Pretty Boy" Floyd?

Charles "Pretty Boy" Floyd, born Charles Arthur Floyd on February 3, 1904, in Adairsville, Georgia, is a notorious figure in American criminal history. He grew up in poverty in Oklahoma, where he earned the nickname "Choc" for his love of Choctaw beer. Floyd's criminal career began during the Great Depression, a time when he turned to crime to escape his dire circumstances. After serving four years in prison for robbery, he emerged with a new moniker, "Pretty Boy," which he later despised. Despite his criminal activities, many locals viewed him as a modern-day Robin Hood, as he was known for allegedly destroying mortgage papers and sharing stolen money with the needy.

Floyd's life was marked by violent bank robberies and run-ins with law enforcement. He became infamous for his reckless behavior and use of a machine gun during bank heists, which led to soaring insurance rates in Oklahoma. One of the most controversial incidents associated with Floyd was the Kansas City Massacre in 1933, where he was accused of being involved in a botched rescue attempt for a fellow gangster. Although he denied his participation, this event solidified his image as a dangerous criminal. After becoming Public Enemy No. 1 following John Dillinger's death, Floyd was ultimately tracked down and shot by FBI agents on October 22, 1934, marking the end of his brief yet sensational crime spree.

Early Life and Education

Charles Arthur Floyd was born on February 3, 1904, in Adairsville, Georgia, and was one of several children in a struggling family. Seeking a better life, the Floyd family relocated to Oklahoma, where they faced extreme poverty while managing a small farm. The hardships of rural life during the Great Depression, particularly the Dust Bowl, would have a profound impact on Floyd's outlook and led him to seek alternative, albeit illegal, means of financial survival. He earned the nickname "Choc" for his fondness for Choctaw beer, which further illustrated his attempts to escape his circumstances.

At 20 years old, Floyd entered into marriage with Ruby Hardgraves, and together they welcomed their son, Charles Dempsey "Jack" Floyd, during Floyd's four-year prison sentence for robbing a Kroger store payroll delivery in St. Louis, Missouri. While incarcerated, Hardgraves divorced him, yet they managed to rekindle their relationship later in the 1930s. Upon his release, Floyd adopted the nickname "Pretty Boy," a label he reportedly grew to despise, as it masked his criminal persona and complicated his identity at a time when he was striving to define himself beyond his criminal past.

Rise of a Notorious Criminal: The Start of Floyd's Criminal Career

Charles "Pretty Boy" Floyd, born Charles Arthur Floyd on February 3, 1904, in Adairsville, Georgia, became notorious for his criminal exploits during the Great Depression. Growing up in a struggling family, Floyd's early life was marked by poverty, which eventually led him down a path of crime. After marrying Ruby Hardgraves and serving a four-year prison sentence for robbery, Floyd transformed into a figure of infamy. Notably, he received his infamous nickname from a girlfriend, though he later despised it. The harsh realities of rural Oklahoma and the economic turmoil of the Dust Bowl pushed Floyd towards a life of bank robbery and violence.

Following his release from prison, Floyd quickly adapted to a life of crime, aligning himself with bootleggers and engaging in violent bank robberies throughout Ohio and other states. His brazen encounters with law enforcement saw him wielding a machine gun, leaving a trail of chaos behind. As he targeted banks, his reputation grew; he was rumored to have destroyed mortgage papers, earning the nickname ‘Robin Hood of the Cookson Hills’ for supposedly aiding struggling communities. This public perception served him well, allowing him to evade capture while fostering a loyal following among Oklahomans who saw him as a rebellious hero, rather than a simple criminal. Floyd's criminal career set the stage for his later involvement in highly publicized events, solidifying his place in American folklore as a notorious outlaw.

Kansas City Massacre and Notoriety

Charles "Pretty Boy" Floyd's notorious reputation escalated dramatically following the Kansas City Massacre on June 17, 1933. This violent incident involved Floyd, along with accomplices Vernon Miller and Adam Richetti, as they attempted to liberate their friend Frank Nash from FBI custody. The plan devolved into chaos when gunfire erupted at the Union Railway Station in Kansas City, Missouri, resulting in the deaths of Nash, two law enforcement officers, and an FBI agent. Although Floyd denied his involvement, the FBI asserted his culpability, solidifying his status as Public Enemy No. 1 after John Dillinger's death.

In the aftermath of the Kansas City Massacre, Floyd evaded capture for over a year, adopting the alias Mr. George Sanders while hiding with his accomplices. Authorities intensified their hunt, and a $23,000 bounty was placed on his head. Incidentally, Floyd was located in an East Liverpool cornfield, leading to a fierce shootout that ultimately resulted in his demise. His last words, "I'm done for; you've hit me twice," echoed the tragic fate of a man whose life of crime had rendered him both feared and idolized, most notably referred to as the "Robin Hood of the Cookson Hills" by locals who romanticized his reckless rebellion against the hardships of the Great Depression.

Final Years and Tragic Death

Charles "Pretty Boy" Floyd, once dubbed "Public Enemy No. 1," found himself in a desperate game of cat and mouse with law enforcement following the Kansas City Massacre. The violent crime of June 17, 1933, in which Floyd allegedly played a role, marked a significant turning point in his life. After John Dillinger's demise, attention shifted to Floyd, who lived in hiding to evade capture. Despite being on the FBI's most-wanted list, he skillfully avoided detection for over a year, adopting the alias Mr. George Sanders and associating with other fugitives. Unfortunately, his luck would soon run out.

The climax of Floyd's tumultuous life came on October 22, 1934, in a cornfield near East Liverpool, Ohio. Following a tip-off about men acting suspiciously near Wellsville, police began to close in on Floyd and his accomplices. A violent shootout ensued when law enforcement discovered him; he sustained critical injuries, resulting in his demise shortly thereafter. Floyd's last words, "I'm done for; you've hit me twice," encapsulated the tragic end of a notorious criminal who once captured the imaginations of many as a modern-day Robin Hood. His funeral drew thousands, solidifying his legacy as an enigmatic figure in American folklore.

Personal Life: Married Life | Children

Charles "Pretty Boy" Floyd married Ruby Hardgraves when he was just 20 years old. Their union was marked by the struggles of poverty, and soon after their marriage, Floyd was imprisoned for a four-year sentence due to a robbery. During his time in prison, Ruby gave birth to their son, Charles Dempsey "Jack" Floyd. Unfortunately, the strain of incarceration led to Ruby filing for divorce, leaving Floyd to grapple with the challenges of fatherhood from behind bars. Despite their separation, there remained a bond between the two, and they rekindled their relationship in the early 1930s, demonstrating the complexities of love and family against a backdrop of crime and hardship.

Floyd's role as a father continued to be shaped by his tumultuous lifestyle. After serving his sentence, he assumed an outlaw persona that would define his later years. Although he was often embroiled in violence and criminal activity, reports suggest that Floyd, at times, endeavored to share his ill-gotten gains with those in need, possibly impacting the life of his son and others in the community. The conflicting aspects of his life—being a devoted father and a notorious criminal—paint a picture of a man trying to balance personal obligations while navigating the extreme pressures of his chosen path. The legacy of his familial relationships, especially with Ruby and Jack, leave behind a complex narrative that intertwines love, loss, and the unpredictable nature of life as an outlaw.

Net Worth and Earning: Salary and Earnings

Charles "Pretty Boy" Floyd, known primarily for his criminal activities during the Great Depression, amassed a significant amount of money through a series of bank robberies and payroll heists. Although specific records of his net worth during his lifetime are sparse, it is estimated that Floyd stole hundreds of thousands of dollars throughout his criminal career. His criminal enterprise was fueled by the desperation of the era and his desire to escape poverty, which led him to target financially-strapped institutions. As he became known as ‘the Robin Hood of the Cookson Hills,’ Floyd’s philanthropic gestures—like destroying mortgage papers—added to his notoriety and public appeal, suggesting that part of his earnings may have been shared with the struggling locals.

Despite his infamy, Floyd's run-ins with the law eventually put an end to his lucrative lifestyle. His earnings were often short-lived, as they were quickly spent on hideouts, accomplices, and covering his tracks from authorities. After becoming "Public Enemy No. 1" following the Kansas City Massacre, a $23,000 bounty was placed on his head, reflecting the vast scale of law enforcement’s desire to apprehend him. Ultimately, Floyd’s life of crime culminated in his death at the hands of FBI agents in 1934, leaving his financial dealings a mix of both ill-gotten gains and squandered opportunities in the face of a law that could not be evaded forever.

FAQs

Who was Charles "Pretty Boy" Floyd?

Charles "Pretty Boy" Floyd was a notorious bank robber and fugitive during the Great Depression era. Born on February 3, 1904, in Adairsville, Georgia, he came from a poor family that relocated to Oklahoma. Floyd earned the nickname "Pretty Boy" from a girlfriend, though he reportedly despised it. He engaged in a life of crime, robbing numerous banks and earning the moniker "Robin Hood of the Cookson Hills" for allegedly helping poor farmers by destroying their mortgage papers during thefts.

What led to Floyd's criminal activities?

The poverty and hardships of the Great Depression compelled Floyd to turn to crime, particularly amid the harsh realities faced by farmers in the "Dust Bowl." After serving a four-year prison sentence for a payroll robbery, he became involved in further criminal endeavors, including bank robberies and bootlegging. His activities became increasingly violent, and his reckless nature made him a prominent figure in the gangster scene of the time, ultimately leading him to commit several high-profile robberies.

What was the Kansas City Massacre?

The Kansas City Massacre, which took place on June 17, 1933, was a violent confrontation involving Floyd, Vernon Miller, and Adam Richetti, who attempted to free their friend Frank Nash from police custody outside Union Railway Station. During this ambush, Nash, as well as two police officers and an FBI agent, were killed. Floyd denied involvement in the massacre; however, law enforcement has continued to link him to the event, marking a significant point in his criminal history.

What happened to Floyd in his final years?

Following the Kansas City Massacre, Floyd became America's "Public Enemy No. 1," evading capture for over a year while living under the alias Mr. George Sanders. His run from the law came to an end in October 1934 after a shootout with FBI agents in Ohio. Floyd was shot twice and famously uttered, "I'm done for; you've hit me twice" before succumbing to his injuries shortly thereafter.

How is Floyd remembered today?

Charles "Pretty Boy" Floyd's life has become the subject of folklore and songs, most notably in Woody Guthrie's "Pretty Boy Floyd," which romanticizes his legacy. Despite his violent criminal activities, local Oklahoma residents often viewed him as a folk hero. His funeral in Akins Cemetery drew thousands of mourners, reflecting the enduring legend surrounding his life and the public's fascination with outlaws during the Great Depression.

What legacy did Floyd leave behind?

Floyd’s legacy includes not only his criminal exploits but also the impact he had on popular culture. He is remembered as a symbol of rebellion against economic oppression. His story was chronicled in several biographies, including Michael Wallis's 1992 publication, "Pretty Boy: The Life and Times of Charles Arthur Floyd," which aims to paint a comprehensive picture of his life, crimes, and the societal conditions that led to his notorious status.