Charles Floyd earned money as a young boy picking cotton in Georgia for nearby growers. His family moved to the rolling Cookson Hills outside the small town of Hanson, Oklahoma in 1911. His father Walter worked as a tenant farmer and may have earned some "extra money" as a bootlegger. It was as a youth in the midwest that Floyd was first exposed to bank robbery. Henry Starr, who was known as the Cherokee Badman (he was one-quarter Cherokee) was a legend throughout Kansas and Oklahoma. Henry's aunt was Belle Starr, matriarch of the Starr clan, a family of outlaws in the old "Indian Territory." Belle also earned a reputation as a spy for Confederates in Missouri and as a temptress who would bribe local authorities with money, booze and her many charms.
Henry Starr apparently captured Charles' attention as word of his exploits reached the young boy. Freed by the governor of Oklahoma on September 24, 1913, Starr waited a year before beginning a three-month spree that saw him rob 14 banks. Starr's picture blazed across the papers underneath 8-column headlines and kids would whisper about the robber's growing legend. Then, on March 25, 1915, Henry was captured during a double robbery in Stroud, Oklahoma reminiscent of the Dalton Gang's raid on Coffeyville, Kansas. Exploiting Starr's reputation, a studio later allowed him to produce and star in the film A Debtor to the Law, about the Stroud robberies. Starr would die in 1921 from a gunshot received during another hold-up.
In 1922 Charles Floyd was caught following a bungled attempt to rob a post office. Although there was not enough evidence to convict him, this first brush with the law nearly cost him jail time for a crime that netted Floyd $3.50. He would not be so lucky in the future.
St. Louis proved a temptation for the Georgian. Its many grocery stores and gas stations only a short drive apart meant easy pickings for the seasoned criminal in 1925. He correctly reasoned that the take from each would be larger because each store would be busier than those in rural Oklahoma. On September_11, 1925, Floyd picked up about $11,000 from the robbery of a Kroger store/warehouse. It was not the only thing the Georgian picked up that day - he got his "Pretty Boy" sobriquet from the description of one of his victims and his first jail term, which he began serving at the Missouri State Penitentiary on a bluff overlooking Jefferson City on December_19, 1925. He was 21 years old
Three and a half years later "Pretty Boy" emerged to a different world. His wife, whom he married after his first hold-up had gotten a divorce and left with his son Dempsey. Federal agents and laws made it more difficult for outlaws to cross state borders to avoid pursuit. In spite of the strengthening of police powers there were still havens that attracted the criminal elements of society.
Kansas City was one such haven, known as a wild town controlled by Tom Prendergast, who was not above consorting with criminals and using mob muscle to enforce his rule. Here, Floyd learned how to deal with criminals from Red Lovett, a bank robber he met in jail. Now divorced, Pretty Boy began to see Juanita Baird, wife of a local drug dealer. She left her husband and moved into an apartment with Floyd. About the same time the police began tailing him and bringing him in for questioning. Floyd always assumed the women's ex-husband had paid them off. Regardless, the close proximity of the police made it difficult for Floyd to "do his job." In November, 1929, Pretty Boy Floyd returned to Cookson Hills for his father's funeral. Walter Floyd had died during an argument with a neighbor, James Mills. Following the funeral, Mills disappeared.
Concerned about the police presence thanks to Juanita Baird, Pretty Boy Floyd headed to East Liverpool, Ohio. On the Ohio River near the Pennsylvania state line, East Liverpool was centrally located in a fairly prosperous area. Floyd and some of his friends selected the city as a headquarters for a rash of robberies they committed from January to March 1930. On March 8, things turned bad for Pretty Boy. Two gang members came in from Akron after a run-in with the police. James Bradley had fired point blank into a policeman's stomach, then been shot by another officer.
Floyd and his gang decided to make a quick getaway after fixing Bradley's wounds. Suddenly, Akron detectives burst into the house, arresting Floyd, Brantley and another man. Brantley would die in the electric chair for the cold-blooded murder of the police officer. Floyd was tried and sentenced to 15 years in the Ohio State Penitentiary for robbery. On the way to the prison, Pretty Boy Floyd escaped from the bathroom on the bus and returned to Kansas City.
In Kansas City he found his old lover, Juanita Baird, her sister Rose, and a new cohort, William Miller. First, Miller and Floyd killed the bothersome ex-husbands of Rose and Juanita, then took off with he girls, heading east and robbing banks for spending money. Time ran out for Miller and Juanita Baird in Toledo, Ohio, when a store clerk called police, having recognized Pretty Boy Floyd from a wanted poster. Floyd killed Officer Castner, who had responded to the call. Miller died, Juanita and Rose were caught. Floyd made it to his car and sped off. As he returned to Cookson Hills in April, Pretty Boy Floyd knew going to the family farm was not an option.
His second home, Cookson Hills afforded Floyd a good deal of protection from the law. Not only that, Floyd had developed a reputation of benevolence with the locals, who tried to protect him from sheriffs and police officers. It was this adoration that brought concern to everybody from Oklahoma Governor William "Alfalfa Bill" Murray to FBI Director J. Edgar Hoover. It would be hard enough to capture Floyd in Cookson Hills without the locals help, but with their help capturing Floyd would be next to impossible. Even when Floyd moved to Little Rock to rekindle his relationship with his wife the authorities could not find him. In April, 1932 Lawman Erv Kelley nearly caught "Pretty Boy" Floyd, but ended up with 7 bullets and a grave instead of Floyd. Kelley did manage to hit Floyd, perhaps even 2 or 3 times with bullets. Floyd laid low again while the wounds healed.
That Fall Adam Richetti and Floyd hit a string of banks, but by early 1933 Richetti was elsewhere while Floyd taught the art of bank robbery to a group of small-time felons. Sometime before May, 1933 Floyd hooked up with Richetti and they began to rob banks. Floyd's fame had been increase and Richetti's was about to when the two were told of a daring escape if Frank Nash from the Union Station in Kansas City. Now accounts of the events of June_17, 1933 differ dramatically, and at least one of Floyd's biographer's does not think he was involved, but FBI field reports tell a different story.
After moving handcuffed killer Frank Nash from the railway station to a car waiting in the front, agents had Nash sit in the front to confuse anyone attempting to assist him. Suddenly, agents spotted a man with an automatic weapon, but before they could react, two other men opened fire, killing Nash and four of six men in the car. Richetti and Floyd were linked to the crime via fingerprint evidence. Once again in the company of Rosa and Juanita Baird, Richetti and Floyd fled to Buffalo, New York. But Floyd himself denied participating in the Kansas City Massacre, as the event became known, in a note scribbled on a postcard addressed to the Kansas City Police.
A year after the Massacre Pretty Boy Floyd surfaced again, in the company of Public Enemy No. 1, John Dillenger. The two may have robbed a South Bend, Indiana bank on June_30, 1934. By the end of the robbery a police officer lay dead an Floyd and Dillenger escaped. Three weeks later John Dillenger would lay dead on a street in Chicago, killed by the FBI. With his death, Pretty Boy Floyd moved to the top of the FBI's Most Wanted list. In October, 1934 Floyd decided to return to Oklahoma.
In Ohio, Floyd ran into bad luck. Adam Richetti was captured by police (Floyd just barely got away). Melvin Purvis was notified of Richetti's capture and of Floyd's escape. On October_22, 1934 Pretty Boy Floyd showed up at the Conkle Farm. Mrs. Conkle fed him, then her son-in-law offered Floyd a ride to town. They didn't get very far. Cars with FBI agents moved to halt the car to question the occupants when Floyd made a run for a nearby forest. Shots rang out and Floyd fell to the ground. He was dead in 15 minutes.