History Daily - The Death of “Pretty Boy” Floyd

Episode Date: October 22, 2025

October 22, 1934. Federal agents track down notorious outlaw Charles “Pretty Boy” Floyd and kill him in a gunfight. This episode originally aired in 2024. Support the show! Join Into History for ad-free listening and more.History Daily is a co-production of Airship and Noiser.Go to HistoryDaily.com for more history, daily.

It's 1 p.m. on September 11th, 1925 in St. Louis, Missouri. Lewis Vazis pulls up outside the Kroger grocery company's head office. As the firm's driver, it's Lewis's job to run errands and shuttle Kroger's bosses around the city. Right now, he's about to deliver a package, and then it's time for his lunch break. But before Lewis can exit the car, the office door opens and slams against the wall. Three men hustle out, each carrying a heavy-looking bag in one hand and a gun in the other. Lewis stays in the car and ducks down. And as he tries to stay out of sight,

he watches the three men climb inside another car that's idling a few yards down the street. And once the men are inside, the car accelerates away. Takes Lewis a couple of seconds to realize he's just witnessed a robbery. He floors the gas pedal and sets off in pursuit. Lewis speeds down the street just in time to see the robber's car turn a corner in the distance. He follows, and as he rounds the same corner, he sees the robber's car parked at the side of the road ahead.

As Lewis closes the gap, two of the robbers jump out of their getaway vehicle and climb into a second car. Both cars set off again, but now Lewis is right on their trail. He grips his steering wheel firmly, wondering which car he should follow if they split up. But then, one of the robbers leans out of his car window and begins firing his pistol. One bullet hits Lewis's car, another whistles past his head, and Lewis quickly realizes, that pursuing these men is not worth the risk. He eases off the gas and reluctantly lets the robbers get away. Then he turns his car around and heads back toward the Kroger offices,

wondering who's going to pay for the bullet hole in the company car. Although Louis Vazis didn't manage to stop the robbers, he will be able to provide detectives with their descriptions, and he'll note that one was a pretty boy with apple cheeks. Four days later, the men will be captured, and 21-year-old Charles Floyd will be identified as the pretty boy. This nickname will stick with him for the rest of his life until his criminal career finally comes to an end

when Pretty Boy Floyd is killed in a shootout with federal agents on October 22, 1934. Hey there, Lindsay Graham here. Before we get to the rest of the show, a quick word about something exciting I'm planning, a live show, me on stage with a microphone in one hand and a fistful of stories in the other. You, hopefully in the audience,

enjoying History Live. If you want to be the first to hear about tour dates, which cities I'll be visiting, special VIP opportunities, and to get a discount on tickets, head to HistoryDailylive.com. That's HistoryDailylive.com. I'm excited to hit the road

and hopefully get to see you, so go to HistoryDailyLive.com. From Noisor and Airship, I'm Lindsay Graham, and this is History Daily. History is made every day. On this podcast, every day, we tell the true stories of the people and events that shaped our world.

Today is October 22nd, 1934, the death of Pretty Boy Floyd. It's November 1930 on board a train traveling through Ohio, five years after the Kroger office robbery. 26-year-old Charles Pretty Boy Floyd walked slowly through the train car as it rocks along the rails. He glances into each compartment he passes until he finally spots one that's empty. He enters, quietly closes the door behind him, and eases open the window. It's been almost two years since Charles was released from prison for his part in the robbery of the Kroger office.

But prison failed to rehabilitate him. Charles immediately returned to a life of crime, and six months ago, he was arrested again and charged with armed robbery and murder. At his trial, he was sentenced to 15 years in prison, but he had no intention of serving any more time behind bars. While being transported to prison by train, he snuck away from his guards during a bathroom break. Now Charles peers through the window at the ground, speeding by beneath him. If he wants to stay out of jail, he's got no choice but to jump. Gathering all his courage,

he clamors up onto the window sill. He waits a moment until the ground beside the tracks looks clear, then he leaves. He lands hard and tumbles over the ground, before eventually coming to a stop in the undergrowth at the side of the tracks. Slowly, he gets up. He's bruised and his hands and face are cut, but otherwise he's in good shape and finally free. Over the next few days, Charles makes his way home to Missouri. He sleeps outside at night and hitches rides during the day. But when he gets back to St. Louis, he's still a fugitive from the law and can't live out in the open, so Charles has no choice but to return to the criminal underworld.

And there, Charles picks up right where he left off. He raids several banks across the Midwest. He's named as a suspect in the murder of two liquor smugglers. And when some lawmen get too close to capturing him, he guns them down. Over the next two years, Charles kills a patrolman in Ohio, a federal agent in Missouri, and a sheriff in Oklahoma. But the newspaper reporters that write about Charles's crimes don't portray him as a ruthless killer. Instead, they transform Charles into something more romantic. They make up stories about him giving away money to the poor, destroying mortgage records to help poverty-stricken farmers avoid debt and throwing coins into the street as he flees the scene of his crimes.

But not everyone views Charles as an attractive anti-hero. To law enforcement, he's nothing more than a cop killer, and officers fear it's only a matter of time before he strikes again. It's the morning of June 17, 1933, at Union Station in Kansas City, Missouri, three years after Charles' pretty boy Floyd escaped a prison sentence by leaping out a train window. Agent Frank Smith escorts another prisoner along the train platform towards the exit. His suspect is handcuffed to him, but Agent Smith isn't taking

any chances. Two other agents walk in front and behind him, clearing a path through the station and keeping a sharp lookout. Agent Smith's prisoner is the notorious bank robber Frank Nash. After a two-decade criminal career, he's one of the most wanted men in America. But yesterday, he was arrested in Arkansas and put on a train to Kansas City, where he faces a long prison sentence. As steam blows down the platform from the locomotive, a local police officer steps forward and asks Agent Smith to follow him. The small group leaves the station and then heads across the parking lot towards a car. Agent Smith climbs into the back seat and Nash awkwardly follows. His wrists still cuffed to Agent Smith's.

But as Agent Smith and Nash struggled to get comfortable, a burst of gunfire rings out across the parking lot. The officers outside the car return fire, but they're quickly overwhelmed. Agent Smith is wondering what to do when the window next to him shatters. Miraculously, he's unharmed, but when he looks to his side, he sees that Frank Nash is not. Nash is slumped in his seat with a bullet hole in the side of his head. After a few seconds, the gunfire stops. All the law enforcement officers around the car are down. Handcuffed to the dead Frank Nash, Agent Smith is defenseless.

and he can hear footsteps approaching. So he makes a split-second decision. He flops forward and plays dead. He holds his breath as the footsteps crunch on broken glass near the car. And just as he thinks he can't hold his breath any longer, another burst of gunfire in the parking lot causes the gunman to turn tail and run. When Agent Smith finally frees himself from the car, he'll discover that Frank Nash's death was an accident.

The men who attacked the police officers were trying to free him, not kill him. But Frank isn't the only fatality of the shootout. Four law enforcement officers are dead, too. And soon a manhunt will begin for the criminals responsible, and the authority's search will quickly narrow in on one man there's certain was involved. Cop killer Charles Pretty Boy Floyd. It's late June 1933 in Washington, D.C., a few days after the shootout in Kansas City. 38-year-old Jay Edgar Hoover approaches a group of reporters in the lobby of the Department of Justice.

As director of the Bureau of Investigation, Hoover leads a team tasked with solving major crimes across state borders. Today, he's briefing the press about a recent attempt to free a prisoner from custody that ended in a firefight. Papers have already dubbed it the Kansas City Massacre. In the days since the shooting, Director Hoover has made this shooting's investigation his agency's top priority. Agents have already worked their sources on the street and identified one of the gunmen, career criminal Vernon Miller. But they're struggling to name the others. Faced with increasing pressure from Hoover, investigators have tentatively suggested

that two of the accomplices could be bank robbers Adam Roshetti and Charles Pretty Boy Floyd. Only circumstantial evidence links them to the crime, but that's enough for Hoover. Summining reporters, Hoover announces that his agents have identified the shooters. As the newsmen scribble in their notebooks, Hoover names the three suspects. Crime reporters exchange pleased looks

they're sure that another story about the notorious Pretty Boy Floyd will boost their paper circulations. But Hoover doesn't reveal that the only physical evidence linking Charles and Adam to the crime is fingerprints lifted from beer bottles in Vernon Miller's house. And when Charles Pretty Boy Floyd himself reads about Hoover's press conference, he responds by mailing a postcard to the Bureau of Investigation.

In it, Charles denies any part in the Kansas City massacre. But Hoover pays no attention to Charles' denial. He's convinced he's got the right man. Six months later, suspect Vernon Miller is discovered dead in a ditch outside Detroit, Michigan. The gruesome nature of Miller's injuries suggest that his death was a gangland hit. But the other two suspects in the massacre remain at large, and the trail goes cold. Director Hoover doesn't forget the case, though, and a year later, he'll decide on a new way to turn up the heat. It's October 10, 1934 in Buffalo, New York, one year. One year, year after the Kansas City Massacre. In the apartment he shares with Adam Roshetti, Charles

Pretty Boy Floyd jumps out of his chair and turns up the radio. He's just heard his name mentioned in the news, and he yells for the others in the room to be quiet. Adam, Charles, and their girlfriends gather around the radio. As they listen, Charles realizes that Bureau of Investigation Director Jay Edgar Hoover is giving another press conference. He says there's been no progress in solving the Kansas City Massacre, but Charles and Adam are still the problem. crimes suspects, and Charles has just been named the Bureau of Investigation's public enemy number one. This announcement puts the spotlight back on Charles and Adams, so they decide to leave Buffalo and lay low in the west. Eight days later, they head out of the city with their girlfriends

under the cover of darkness, but the group doesn't make it far. While driving through heavy fog at 3 a.m. on the outskirts of Wellsville, Ohio, their car slides off the road and hits a telegraph pole. None of them are hurt in the crash, but the car is damaged enough that they need a tow truck. Charles and Adams' mugshots had been widely circulated in the newspapers, so they send their girlfriends to get help while they stay in the car. But a passing motorist thinks they look suspicious when he spots him at the roadside, and he reports Charles and Adam to the police. The local chief wants to make sure these loitering men aren't up to any trouble,

so he sets off with a couple of patrolmen to investigate. Charles and Adam can't risk being identified. And when they see a police car approaching, they try to sneak into a nearby field before they can be seen. But it's too late. Spotting Charles and Adam attempting to flee, the police officers climb out of their car and give chase. Charles draws his gun and opens fire on the policeman.

Then he turns and sprints away through the darkness. He and Adam run in opposite directions to split up their pursuers and the cops choose to follow Adam. He's quickly captured, and news of his arrest is soon reported to the Bureau of Investigation. Agents there conclude that the man who got away must have been Adams' partner in crime, Charles Pretty Boy Floyd. So later that day, federal agents will descend on Ohio to scour the state for their number one fugitive. They'll leave no stone unturned in the hunt for the notorious Pretty Boy Floyd, but as the net closes in around him, Charles will be determined to go down fighting.

It's October 22nd, 1934 in East Ohio, three days after the arrest of Adam Roshetti. Bureau of Investigation Agent Winfred E. Hopton drives his car slowly along the rural backroads close to the state border. In the passenger seat beside him, another agent scans the cornfields and farm buildings for any side of movement. Two days ago, Agent Hopton was summoned to Ohio to take part in a manhunt. Bank robber Adam Roshetti had been arrested, but the country's most wanted for fugitive was still on the run. Earlier today, though, a call came in claiming that Charles Pretty Boy Floyd had been spotted in the nearby town of East Liverpool. Now agents are scouring the surrounding area. Agent Hopton tries to keep a keen eye out. When the agent beside him

gives a sudden shout and points through the windshield, he spotted a car moving out from behind a barn. Hopton slows down and the other car quickly reverses back out of sight as if its driver is trying to hide. The two bureau agents glanced at each other because that seems suspicious. Agent Hopton pulls over to the side of the road close to the bar, but as he opens his car door, shots are fired. Agent Hopton and his colleague ducked down. Grabbing the radio, Hopton calls for backup, and it's not long before other agents are on the scene. A brief firefight follows, but whoever's inside the barn is heavily outgunned, and it's not long before the shots fall silent. Agent Hopton emerges from cover, his handcuffs at the ready.

Reaching the barn, he finds the gunman, writhing on the ground in agony. Opton recognizes him at once. It's Charles Pretty Boy Floyd, the man they've all been searching for, and he doesn't have long to live. With his dying words, he'll insist he had nothing to do with the Kansas City massacre. There's plenty he was guilty of during his life, but not that. Following Charles's death, the shooters in that massacre will never be definitively identified. but that won't stop the Bureau of Investigation from claiming they got their man.

Director Hoover will use the successful manhunt of Charles Floyd to secure more funding for his organization. And the following year, the Bureau of Investigation would become the FBI, a new crime-fighting agency that rose to fame with a year-long manhunt that ended with Charles Pretty Boy Floyd's death in a shootout on October 22, 1934. Next on History Daily, October 20, 3rd, 1958. Russian poet Boris Pasternak is awarded the Nobel Prize in Literature for his novel Dr. Chivago, only for the Soviet Union to force him to refuse the honor. From Noiser and Airship,

this is History Daily, hosted, edited and executive produced by me, Lindsay Graham, audio editing by Mohamed Shazi, sound design by Matthew Phillips, music by Throne. This episode is written in research by Scott Reeves, edited by Dorian Marina, managing producer Emily Burke, executive producers are William Simpson for airship, Pascal Hughes for Noiser.