The Rise and Fall of Pretty Boy Floyd: Corn Liquor and Submachine Guns

0:00 [Music] In October of 1934, federal agents surrounded a cornfield in East Liverpool, Ohio. The man they were hunting had robbed dozens of banks and was accused of killing four law enforcement officers in a single morning. He was also, depending on who you talk to in rural Oklahoma, somebody's neighbor, the guy who paid your doctor bill when you had nothing. This is the story of Pretty Boy Floyd.

0:43 [Music] Welcome to 10 Minute Murder. Charles Arthur Floyd was born February 3rd, 1904 in a daresville, Georgia. The fourth of eight children and a family that survived on tenant farming and Baptist discipline. Tenant farming in the post reconstruction south was a system designed to keep you exactly where you started. You worked, land that belonged to someone else, gave that person a percentage of everything that you grew, and hoped the harvest left enough to carry you through the next year. His father, Walter Lee Floyd, ran a household where the children functioned as a labor force that happened to share a last name. Formal education was secondary. The fields came first and they always came early.

1:33 In 1911, the family relocated to Sequoia County, Oklahoma near the town of Aikens, on the edge of a rugged stretch of terrain called the Cooxon Hills. Those hills had sheltered outlaw since the Confederate guerrillas used the terrain as sanctuary after the Civil War. The tradition of moving corn liquor through those hills predated prohibition by generations. Prohibition just made it more lucrative. The neighbors were already professionals by the time the Floyd's arrived. Charles grew up inside all of it. It was practical and it was normal. It was how things got done when the cotton prices dropped, which they did with reliable frequency. At 15, Charles left home to join a harvest crew moving through Kansas and Oklahoma. He spent long stretches in the company of drifters and enterant workers. Men with stories about an entirely different way to live. He was 15 and he ran the numbers. A full week of brutal harvest labor produced few dollars. One successful robbery produced the same amount in a single evening.

2:37 Nobody explained this to him. He arrived at that conclusion entirely himself. In 1922, he was arrested for stealing $3.50 from a local post office, an amount that made it a federal offence. The American Justice System introduced itself to Charles' Arthur Floyd over $3.50 and the introduction was not a cordial one. By 1924, Charles married Ruby Hardgraves, a 16-year-old daughter of a local tenant farmer. And their son Charles Dempsey Floyd arrived within the year. Charles genuinely tried to make legitimate work function. He took jobs in the oil fields, but the wages didn't reach far enough and he had connected with a man named John Hilderbrand, a veteran thief running an informal apprenticeship in payroll robbery. Charles enrolled effectively.

3:28 In September 1925, he was arrested for a Croger payroll robbery in St. Louis, Missouri and received a five-year sentence at the Missouri State Penitentiary in Jefferson City. A 1920 state penitentiary was not a rehab environment. Ruby filed for divorce in 1929, citing neglect, which is a restrained way to describe the situation. The emotional and financial ties between Charles and Ruby and their son never fully dissolved in any practical sense. He sent stolen money home when he had it, which turned out to be pretty often. When Floyd was released in 1929, he attempted legitimate employment again. He applied to the Seminole oil fields. His criminal record surfaced and he was terminated. Local law enforcement arrested him repeatedly for vagrancy and suspicion, which is legal language for, we know what you are.

4:20 He eventually drifted toward Kansas City. Kansas City in that era operated on two parallel systems that everyone understood and nobody officially acknowledged. Tom Pindagrast ran the political machine. Mob figured John LaSia managed everything else. In the Kansas City underworld, Floyd's reputation as a skilled, reliable, stick-up man built steadily. He was also, by all accounts, unusually handsome and surprisingly courteous in day-to-day life, which the organized crime community apparently found disorienting. Somewhere in that world, someone started calling him pretty boy. The exact origin shifts by account, some credit card player at a boarding house, others a robbery victim. Floyd despised that nickname for the rest of his life, which is understandable.

5:08 Nobody wants their professional identity permanently defined by someone they robbed. By the early 1930s, the Depression had broken rule Oklahoma in ways that are genuinely difficult to comprehend from this distance. Banks were foreclosing on farms that families had worked for generations. The federal government felt about his present and helpful as a notice in the mail. The story, moving through cooks and hills, was that when Floyd robbed a bank, he destroyed mortgage documents. He freed people from debts they could never realistically repay. Hard evidence for systematic mortgage burning is scarce. But the belief in it was absolute, and that belief did real psychological work. He paid doctors bills, handed bags of cash to WPA road workers, and left money under pillows at farmhouses where he slept. Whether every detail holds up to scrutiny, the cumulative effect was substantial and sustained. He was almost a Robin Hood of the Great Depression era. The people of cooks and hills protected him actively.

6:08 When federal agents came through asking questions about pretty boy Floyd, they left without answers. These agents were trying to run an informant network in a community that viewed their target as a neighbor and a provider. That is, structurally not a law enforcement problem. It's a trust problem, and the federal government had earned almost none of it out there. On June 17, 1933, everything shifted. A federal prisoner named Frank Nash, a career bank robber with extensive underworld ties, was being transported through Kansas City's Union Station when gunmen opened fire with Thompson machine guns. Four law enforcement officers and Nash himself were killed. The Kansas City massacre was among the most violent events in American law enforcement history to that point, and Jay Edgar Hoover's Bureau of Investigation needed a name to attach to it. They landed on pretty boy Floyd. The identification relied on disputed eyewitness accounts and the regional proximity of his partner, Adam Ritchettie. Floyd denied involvement until his death. Historians, Michael Wallace, and Robert Unger later identified serious problems with the identification. Witnesses had described one of the shooters sustaining a shoulder wound. When Floyd's body was examined in October of 1934, no such injury existed. Underworld sources with direct knowledge insisted Floyd was somewhere else, and Hoover had clear motivation to assign a famous folk hero to a cop killing. The massacre gave Hoover what he needed to pass sweeping 1934 legislation. The Bureau became the FBI.

7:44 agents gained arrest authority across state lines, and the National Firearms Act was born. Floyd's name was attached to all of it, regardless of what he actually did that morning at Union Station. After John Dillinger was killed, and July of 1934, Floyd inherited the title of public enemy number one. Hoover moved to Cutoff Support Networks systematically, threatening Floyd's relatives in Ohio and Oklahoma, with federal conspiracy charges for providing him food or shelter. Floyd spent those final months in constant motion. On October 20th, 1934, Floyd and Ritchettie crashed their car near Wellsville, Ohio. They hid in the woods. Local residents spotted them. Ritchettie was captured in a shootout with local police. Floyd ran, consistent with everything previously documented about him.

8:34 Two days later, October 22nd, 1934, agents cornered him behind a corn crib on Ellen Conkel's farm outside East Liverpool. He ran across an open field toward a tree line. He was shot. He fell. He was carried to a nearby farmhouse where he died. The official FBI account filed by Agent Melvin Purvis states that Floyd was armed and in flight when agents fired. A retired East Liverpool police officer named Chester Smith claimed decades later that Floyd was wounded and disarmed on the ground. Purvis ordered another agent to finish the job. The FBI counted with ballistic records and autopsy findings that did not match the rifle Smith described and no other witness present that day cooperated the execution account until many years later. That particular question remains genuinely unresolved.

9:27 Melvin Purvis credited with closing both the Dillonshire and Floyd cases did not enjoy that success for long. Hoover, jealous of Purvis' national celebrity drove a sustained campaign of reassignments and obstruction until Purvis resigned in 1935. He died on February 29th, 1960 from a gunshot wound to the head, officially ruled a suicide. His family questioned that ever since. Hoover sent no condolences and did not attend the funeral of his most celebrated agent. Ruby Hardgraves lived until 1970. Their son Charles Dempsey Floyd lived until 1999 in California. In the few interviews he gave, he described his father as a man shaped by the world he was handed. Push toward choices a different life might never have required. Between 20,000 and 40,000 people attended Charles Arthur Pretty Boy Floyd's funeral at Akhen Cemetery in Oklahoma. One of the largest gatherings in state history. He was known as Chalk to the people who loved him. Public enemy number one to a government that needed him to be and to tens of thousands standing in that cemetery in October of 1934. Just someone worth showing up for one last time.

10:51 Thanks for listening to 10 Minute Murder, bingeable true crime stories. I'm Joe, I'm the host. Hi. Here's an email, Subjects, The Re-Listen Test. Hey Joe, I've started re-listening to older episodes while driving down I-5 near Eugene and it's interesting how much I forgot the second time around. It almost feels like I'm hearing the stories fresh again. Do you ever go back and listen to see how they hold up? Hannah in Eugene, Oregon. Hannah, no I do not. Well, I mean I say I don't, I have, but I don't make it a habit. And the reason is it might be weird for you to hear but I don't like listening to my own voice. It's awkward. I'm hypercritical of myself and if I go back and listen to older episodes I start critiquing myself saying I should have said this a little differently. I should have thrown this sentence in there. I should have done that this way. Why do I sound that way? That sounds terrible. I must have had allergies that day. Like all of that starts going through my head.

11:50 So I don't make it a habit to re-list into any of my episodes or anything that I record actually. But yeah, there is a small group, a small club of people that listen to 10-minute murder and they've listened to all of the episodes and they've gone back and listened to all of the episodes again. And then even a smaller group of people that have listened to all of the episodes the third time. And there are, I don't know how, I don't really keep up like a lot of people do, but like 600 something episodes at this point. That's a lot of episodes. I know they're only like 10 or so minutes long, but that's still a lot of episodes for you to go back and listen to. So I genuinely appreciate all of the listening that you're doing. Now I'm assuming if you're doing all that listening, you're also sharing the podcast with your friends and your family. I'm not talking exactly just to you Hannah and Eugene Oregon, which by the way Oregon is beautiful. I went there last year. I want to go back again very soon. Maybe one of the prettiest states in this whole country, Oregon. But anyway, make sure if you're doing all this listening, you're sharing the podcast with your friends and your family because that's how it grows. If you're a brand new listener to this podcast, make sure you hit subscribe wherever you're listening right now. And I do need to tell you about a brand new podcast that is not exactly brand new at this point. It's been out for a little while, but it's still building.

13:05 I still need you to go over and check it out. It's called True Crime Blueprint. It's available at most places. This one is, and again, it's called True Crime Blueprint. And that's going to do it. That's your episode for today. Thank you again for listening to 10 Minute Murder. See you next time.