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Floyd was born in Georgia but grew up in Oklahoma, spending considerable time in nearby Kansas, Arkansas and Missouri. He was first arrested at the age of 18 after he stole $3.50 in coins from a local post office. Three years later he was arrested for a payroll robbery on September 16, 1925 in St. Louis, Missouri, and served five years in prison.

When paroled, Floyd vowed that he would never see the inside of another prison. Entering into partnerships with more established criminals in the Kansas City underworld, he committed a series of bank robberies over the next several years; it was during this period that he acquired the nickname "Pretty Boy." According to one account, when the payroll master targeted in a robbery described the three perpetrators to the police, he referred to Floyd as "a mere boy — a pretty boy with apple cheeks." (Other accounts claim the nickname was bestowed by a woman as a compliment.) Like his contemporary Baby Face Nelson, Floyd hated his nickname.

In 1929, he faced numerous arrests. On March 9, he was arrested in Kansas City on investigation and again on May 6 for vagrancy and suspicion of highway robbery, but was released the next day. Two days later, he was arrested in Pueblo, Colorado, charged with vagrancy. He was fined $50.00 and sentenced to 60 days in jail.

In November 1929, he traveled to Oklahoma for his father's funeral. Floyd's father, who was unarmed, had been killed by his neighbor Jim Mills who was acquitted despite an eyewitness account who later went missing.

One of the members of Floyd's gang, "Frank Mitchell" was arrested in Akron, Ohio, on March 8, 1930, charged in the investigation of the murder of an Akron police officer, who had been killed during a robbery that evening.

The law next caught up with Floyd in Toledo, Ohio, where he was arrested on suspicion on May 20, 1930; he was sentenced on November 24, 1930, to 12–15 years in Ohio State penitentiary for the Sylvania Ohio Bank Robbery but he escaped.

Floyd was a suspect in the deaths of bootlegging brothers Wally and Boll Ash of Kansas City. They were found dead in a burning car on March 25, 1931. A month later on April 23, members of his gang killed Patrolman R. H. Castner of Bowling Green, Ohio, and on July 22 Floyd himself killed ATF Agent C. Burke in Kansas City, Missouri.

In 1932, former sheriff Erv Kelley of McIntosh County, Oklahoma, tried to ambush/arrest Floyd; he was killed on April 7. In November of that year, three members of Floyd's gang attempted to rob the Farmers and Merchants Bank in Boley, Oklahoma.

Kansas City massacre

Floyd and Adam Richetti became the primary suspects in a June 17, 1933, gunfight known as the "Kansas City massacre" that resulted in the deaths of four law enforcement officers.Though J. Edgar Hoover used the incident as ammunition to further empower the FBI to pursue Floyd, historians are divided as to whether or not he was involved.

The gunfight was an attack by Vernon Miller and accomplices on lawmen escorting robber Frank "Jelly" Nash to a car parked at the Union Railway Station in Kansas City, Missouri. Two Kansas City, Missouri officers, Detective William Grooms[7] and Patrolman Grant Schroder; McAlester, Oklahoma Police Chief Otto Reed; and FBI Special Agent Ray Caffrey were killed. Nash was also killed as he was sitting in the car. Two other Kansas City police officers survived by slumping forward in the backseat and feigning death. As the gunmen inspected the car, another officer responded from the station and fired at them, forcing them to flee. Miller was found dead on November 27, 1933, outside Detroit, Michigan, beaten and strangled.

Miller's accomplices stopped at the gas station of Ben Homer Eyerly in Gardner, Kansas, as they fled the scene. "Papa Ben" Eyerly was used to sending out his son Clarence to pump gas, but on this day sent Clarence to lock himself in the back of the store. "Papa Ben" pumped the gas for two bloodied gangsters and they paid. No questions were asked.

Floyd and Richetti were alleged to have been Miller's accomplices. Factors weighing against them included their apparent presence in Kansas City at the time, eyewitness identifications (which have been contested), Richetti's fingerprint said to have been recovered from a beer bottle at Miller's hideout, an underworld account naming Floyd and Richetti as the gunmen, and Hoover's firm advocacy of their guilt. Fellow bank robber Alvin Karpis, an acquaintance of Floyd's, claimed that Floyd confessed involvement to him. On the other side of the issue, the bandit alleged to have been Floyd was supposed to have been wounded by a gunshot to the shoulder in the attack, and Floyd's body showed no sign of this injury when examined later. The underworld account identifying Floyd and Richetti as the killers was offset by equally unreliable underworld accounts proclaiming their innocence or identifying others. The Floyd family has maintained that while Floyd owned up to many other crimes, he vehemently denied involvement in this one, as did Richetti. It has also been contended that this crime would have been inconsistent with Floyd's other criminal acts, as he was not otherwise known as a hired gun or (especially) a hired killer.

Shortly after the attack, Kansas City police received a postcard dated June 30, 1933, from Springfield, Missouri, which read: "Dear Sirs- I- Charles Floyd- want it made known that I did not participate in the massacre of officers at Kansas City. Charles Floyd".[citation needed] The police department believed the note to be genuine. Floyd also reportedly denied involvement in the massacre to the FBI agents who had fatally wounded him. In addition, a recent book on the massacre attributes at least some of the killing to friendly fire by a lawman who was unfamiliar with his weapon, based on ballistic tests.

Death

On October 22, 1934, Floyd was killed in an apple orchard near East Liverpool, Ohio, while being pursued by local law officers and FBI agents led by Melvin Purvis.Varying accounts exist as to who shot him and the manner in which he was killed.

Having narrowly escaped ambush by FBI agents and other law enforcement agencies several times after the Kansas City Massacre, Floyd had a stroke of bad luck. On October 18, 1933, he and Richetti left Buffalo, New York, and slid their vehicle into a telephone pole during a heavy fog. No one was injured, but the car was disabled. Fearing they would be recognized, Floyd and Richetti sent two female companions to retrieve a tow truck; the women would then accompany the tow truck driver into a town and have the vehicle repaired while the two men waited by the roadside.

After dawn on October 19, motorist Joe Fryman and his son-in-law passed by, observing two men dressed in suits lying by the roadside. Feeling it was suspicious, he informed Wellsville, Ohio, Police Chief John H. Fultz. Three officers, including Fultz, investigated. When Richetti saw the lawmen, he fled into the woods, pursued by two officers, while Fultz went toward Floyd. Floyd immediately drew his gun and fired, and he and Fultz engaged one another in a gunfight, during which Fultz was wounded in the foot. After wounding Fultz, Floyd fled into the forest. The other two officers enlisted the help of local retired police officer Chester K. Smith, a former sniper during World War I, and subsequently captured Richetti. Floyd remained on the run, living on fruit, traveling on foot, and quickly becoming exhausted.

At least three accounts exist of the following events: one given by the FBI, one by other people in the area, and one by local law enforcement. The accounts agree that, after obtaining some food at a local pool hall owned by Charles Joy, a friend of Floyd's, Floyd hitched a ride in an East Liverpool neighborhood on October 22, 1934. He was spotted by the team of lawmen, at which point he broke from the vehicle and fled toward the treeline. Local retired officer Chester Smith fired first, hitting Floyd in the right arm, knocking him to the ground. At this point, the three accounts diverge; the FBI agents later attempted to claim all the credit, denying local law enforcement were even present at the actual shooting.[citation needed] According to the local police account, Floyd regained his footing and continued to run, at which point the entire team opened fire, knocking him to the ground. Floyd died shortly thereafter from his wounds.

According to the FBI, four FBI agents, led by Purvis, and four members of the East Liverpool Police Department, led by Chief Hugh McDermott, were searching the area south of Clarkson, Ohio, in two separate cars. They spotted a car move from behind a corn crib, and then move back. Floyd then emerged from the car and drew a .45 caliber pistol, and the FBI agents opened fire. Floyd reportedly said: "I'm done for. You've hit me twice."

However, Chester Smith, the retired East Liverpool Police Captain and sharpshooter, described events differently in a 1979 interview for Time magazine. Smith, who was credited with shooting Floyd first, stated that he had deliberately wounded, but not killed, Floyd. He then added: "I knew Purvis couldn't hit him, so I dropped him with two shots from my .32 Winchester rifle." According to Smith's account, after being wounded, Floyd fell and did not regain his footing. Smith then disarmed Floyd. At that point, Purvis ran up and ordered: "Back away from that man. I want to talk to him." Purvis questioned Floyd briefly, and after receiving curses in reply ordered agent Herman "Ed" Hollis to "Fire into him." Hollis then shot Floyd at point-blank range with a submachine gun, killing him. The interviewer asked if there was a cover-up by the FBI, and Smith responded: "Sure was, because they didn't want it to get out that he'd been killed that way." This account is extremely controversial. If true, Purvis effectively executed Floyd without benefit of judge or jury.

FBI agent Winfred E. Hopton disputed Chester Smith's claim in a letter to the editors of Time Magazine, that appeared in the November 19, 1979, issue, in response to the Time article "Blasting a G-Man Myth." In his letter he stated that he was one of four FBI agents present when Floyd was killed, on a farm several miles from East Liverpool, Ohio. According to Hopton, members of the East Liverpool police department arrived only after Floyd was already mortally wounded. He also claimed that when the four agents confronted Floyd, Floyd turned to fire on them, and two of the four killed Floyd almost instantly. Additionally, while Smith's account said that Herman Hollis shot the wounded Floyd on Purvis's order, Hopton claimed that Hollis was not present. Hopton also stated Floyd's body was transported back to East Liverpool in Hopton's personal car.

Floyd's body was embalmed and briefly viewed at the Sturgis Funeral Home, in East Liverpool, Ohio before being sent on to Oklahoma. Floyd's body was placed on public display in Sallisaw, Oklahoma. His funeral was attended by between 20,000 and 40,000 people and remains the largest funeral in Oklahoma history. He was buried in Akins, Oklahoma.