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

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[Music]

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In October of 1934, federal agents surrounded a cornfield in East Liverpool, Ohio.

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The man they were hunting had robbed dozens of banks and was accused of killing four

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law enforcement officers in a single morning. He was also, depending on who you

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talk to in rural Oklahoma, somebody's neighbor, the guy who paid your doctor bill

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when you had nothing. This is the story of Pretty Boy Floyd.

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[Music]

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Welcome to 10 Minute Murder. Charles Arthur Floyd was born February 3rd,

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1904 in a daresville, Georgia. The fourth of eight children and a family that survived

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on tenant farming and Baptist discipline. Tenant farming in the post reconstruction

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south was a system designed to keep you exactly where you started. You worked,

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land that belonged to someone else, gave that person a percentage of everything that you grew,

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and hoped the harvest left enough to carry you through the next year. His father, Walter

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Lee Floyd, ran a household where the children functioned as a labor force that happened to share a

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last name. Formal education was secondary. The fields came first and they always came early.

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In 1911, the family relocated to Sequoia County, Oklahoma near the town of Aikens,

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on the edge of a rugged stretch of terrain called the Cooxon Hills. Those hills had sheltered

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outlaw since the Confederate guerrillas used the terrain as sanctuary after the Civil War.

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The tradition of moving corn liquor through those hills predated prohibition by generations.

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Prohibition just made it more lucrative. The neighbors were already professionals by the time

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the Floyd's arrived. Charles grew up inside all of it. It was practical and it was normal.

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It was how things got done when the cotton prices dropped, which they did with reliable frequency.

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At 15, Charles left home to join a harvest crew moving through Kansas and Oklahoma. He spent

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long stretches in the company of drifters and enterant workers. Men with stories about an entirely

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different way to live. He was 15 and he ran the numbers. A full week of brutal harvest labor

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produced few dollars. One successful robbery produced the same amount in a single evening.

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Nobody explained this to him. He arrived at that conclusion entirely himself. In 1922,

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he was arrested for stealing $3.50 from a local post office, an amount that made it a federal offence.

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The American Justice System introduced itself to Charles' Arthur Floyd over $3.50 and the

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introduction was not a cordial one. By 1924, Charles married Ruby Hardgraves, a 16-year-old daughter

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of a local tenant farmer. And their son Charles Dempsey Floyd arrived within the year. Charles

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genuinely tried to make legitimate work function. He took jobs in the oil fields, but the wages

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didn't reach far enough and he had connected with a man named John Hilderbrand, a veteran thief

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running an informal apprenticeship in payroll robbery. Charles enrolled effectively.

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In September 1925, he was arrested for a Croger payroll robbery in St. Louis, Missouri

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and received a five-year sentence at the Missouri State Penitentiary in Jefferson City.

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A 1920 state penitentiary was not a rehab environment. Ruby filed for divorce in 1929,

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citing neglect, which is a restrained way to describe the situation. The emotional and financial ties

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between Charles and Ruby and their son never fully dissolved in any practical sense.

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He sent stolen money home when he had it, which turned out to be pretty often.

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When Floyd was released in 1929, he attempted legitimate employment again. He applied to the

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Seminole oil fields. His criminal record surfaced and he was terminated. Local law enforcement

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arrested him repeatedly for vagrancy and suspicion, which is legal language for, we know what you are.

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He eventually drifted toward Kansas City. Kansas City in that era operated on two parallel

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systems that everyone understood and nobody officially acknowledged. Tom Pindagrast ran the

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political machine. Mob figured John LaSia managed everything else. In the Kansas City

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underworld, Floyd's reputation as a skilled, reliable, stick-up man built steadily. He was also,

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by all accounts, unusually handsome and surprisingly courteous in day-to-day life,

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which the organized crime community apparently found disorienting.

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Somewhere in that world, someone started calling him pretty boy.

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The exact origin shifts by account, some credit card player at a boarding house,

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others a robbery victim. Floyd despised that nickname for the rest of his life, which is understandable.

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Nobody wants their professional identity permanently defined by someone they robbed.

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By the early 1930s, the Depression had broken rule Oklahoma in ways that are genuinely difficult

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to comprehend from this distance. Banks were foreclosing on farms that families had worked for

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generations. The federal government felt about his present and helpful as a notice in the mail.

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The story, moving through cooks and hills, was that when Floyd robbed a bank,

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he destroyed mortgage documents. He freed people from debts they could never realistically repay.

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Hard evidence for systematic mortgage burning is scarce. But the belief in it was absolute,

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and that belief did real psychological work. He paid doctors bills, handed bags of cash to

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WPA road workers, and left money under pillows at farmhouses where he slept. Whether every

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detail holds up to scrutiny, the cumulative effect was substantial and sustained. He was almost a

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Robin Hood of the Great Depression era. The people of cooks and hills protected him actively.

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When federal agents came through asking questions about pretty boy Floyd, they left without answers.

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These agents were trying to run an informant network in a community that viewed their target as

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a neighbor and a provider. That is, structurally not a law enforcement problem. It's a trust problem,

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and the federal government had earned almost none of it out there. On June 17, 1933, everything

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shifted. A federal prisoner named Frank Nash, a career bank robber with extensive underworld ties,

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was being transported through Kansas City's Union Station when gunmen opened fire with Thompson

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machine guns. Four law enforcement officers and Nash himself were killed. The Kansas City massacre

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was among the most violent events in American law enforcement history to that point,

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and Jay Edgar Hoover's Bureau of Investigation needed a name to attach to it. They landed on pretty

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boy Floyd. The identification relied on disputed eyewitness accounts and the regional proximity of

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his partner, Adam Ritchettie. Floyd denied involvement until his death. Historians, Michael Wallace,

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and Robert Unger later identified serious problems with the identification. Witnesses had

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described one of the shooters sustaining a shoulder wound. When Floyd's body was examined in October

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of 1934, no such injury existed. Underworld sources with direct knowledge insisted Floyd was somewhere

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else, and Hoover had clear motivation to assign a famous folk hero to a cop killing. The massacre

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gave Hoover what he needed to pass sweeping 1934 legislation. The Bureau became the FBI.

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agents gained arrest authority across state lines, and the National Firearms Act was born. Floyd's name

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was attached to all of it, regardless of what he actually did that morning at Union Station.

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After John Dillinger was killed, and July of 1934, Floyd inherited the title of public enemy number one.

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Hoover moved to Cutoff Support Networks systematically, threatening Floyd's relatives in Ohio and

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Oklahoma, with federal conspiracy charges for providing him food or shelter. Floyd spent those

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final months in constant motion. On October 20th, 1934, Floyd and Ritchettie crashed their car near

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Wellsville, Ohio. They hid in the woods. Local residents spotted them. Ritchettie was captured in a

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shootout with local police. Floyd ran, consistent with everything previously documented about him.

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Two days later, October 22nd, 1934, agents cornered him behind a corn crib on Ellen Conkel's farm

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outside East Liverpool. He ran across an open field toward a tree line. He was shot. He fell. He was

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carried to a nearby farmhouse where he died. The official FBI account filed by Agent Melvin Purvis

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states that Floyd was armed and in flight when agents fired. A retired East Liverpool police officer

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named Chester Smith claimed decades later that Floyd was wounded and disarmed on the ground. Purvis

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ordered another agent to finish the job. The FBI counted with ballistic records and autopsy findings

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that did not match the rifle Smith described and no other witness present that day cooperated the

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execution account until many years later. That particular question remains genuinely unresolved.

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Melvin Purvis credited with closing both the Dillonshire and Floyd cases did not enjoy that success

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for long. Hoover, jealous of Purvis' national celebrity drove a sustained campaign of reassignments

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and obstruction until Purvis resigned in 1935. He died on February 29th, 1960 from a gunshot wound to

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the head, officially ruled a suicide. His family questioned that ever since. Hoover sent no

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condolences and did not attend the funeral of his most celebrated agent. Ruby Hardgraves lived

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until 1970. Their son Charles Dempsey Floyd lived until 1999 in California. In the few interviews he

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gave, he described his father as a man shaped by the world he was handed. Push toward choices a

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different life might never have required. Between 20,000 and 40,000 people attended Charles Arthur

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Pretty Boy Floyd's funeral at Akhen Cemetery in Oklahoma. One of the largest gatherings in

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state history. He was known as Chalk to the people who loved him. Public enemy number one to a

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government that needed him to be and to tens of thousands standing in that cemetery in October

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of 1934. Just someone worth showing up for one last time.

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Thanks for listening to 10 Minute Murder, bingeable true crime stories. I'm Joe, I'm the host. Hi.

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Here's an email, Subjects, The Re-Listen Test. Hey Joe, I've started re-listening to older episodes

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while driving down I-5 near Eugene and it's interesting how much I forgot the second time around.

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It almost feels like I'm hearing the stories fresh again. Do you ever go back and listen to see how

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they hold up? Hannah in Eugene, Oregon. Hannah, no I do not. Well, I mean I say I don't, I have,

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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

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listening to my own voice. It's awkward. I'm hypercritical of myself and if I go back and listen to

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older episodes I start critiquing myself saying I should have said this a little differently. I should

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have thrown this sentence in there. I should have done that this way. Why do I sound that way? That

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sounds terrible. I must have had allergies that day. Like all of that starts going through my head.

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So I don't make it a habit to re-list into any of my episodes or anything that I record actually.

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But yeah, there is a small group, a small club of people that listen to 10-minute murder and they've

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listened to all of the episodes and they've gone back and listened to all of the episodes again.

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And then even a smaller group of people that have listened to all of the episodes the third time.

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And there are, I don't know how, I don't really keep up like a lot of people do, but like 600

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something episodes at this point. That's a lot of episodes. I know they're only like 10 or so

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minutes long, but that's still a lot of episodes for you to go back and listen to. So I genuinely

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appreciate all of the listening that you're doing. Now I'm assuming if you're doing all that listening,

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you're also sharing the podcast with your friends and your family. I'm not talking exactly just to

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you Hannah and Eugene Oregon, which by the way Oregon is beautiful. I went there last year. I want to

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go back again very soon. Maybe one of the prettiest states in this whole country, Oregon. But anyway,

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make sure if you're doing all this listening, you're sharing the podcast with your friends and your

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family because that's how it grows. If you're a brand new listener to this podcast, make sure you hit

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subscribe wherever you're listening right now. And I do need to tell you about a brand new podcast that

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is not exactly brand new at this point. It's been out for a little while, but it's still building.

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I still need you to go over and check it out. It's called True Crime Blueprint. It's available

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at most places. This one is, and again, it's called True Crime Blueprint. And that's going to do it.

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That's your episode for today. Thank you again for listening to 10 Minute Murder. See you next time.