Infamous America - PRETTY BOY FLOYD Ep. 4 | “Never Surrender”

Episode Date: February 16, 2022

Charles “Pretty Boy” Floyd is firmly established as a bank robber and a dangerous outlaw. He is also a Robin-Hood-style hero to many in Oklahoma. He reconnects with his ex-wife and son and moves to Tulsa. But the law tracks him down and sets an ambush on a farm outside the city. Floyd and his partner shoot it out with a local sheriff rather than surrender, and the confrontation will add to Floyd’s legend as well as make him one of the most wanted men in America. Check out the Jordan Harbinger show today! jordanharbinger.com/start To advertise on this podcast, please email [e-mail] Join Black Barrel+ for ad-free episodes and bingeable seasons: blackbarrel.supportingcast.fm/join For more details, please visit www.blackbarrelmedia.com. Our social media pages are: @blackbarrelmedia on Facebook and Instagram, and @bbarrelmedia on Twitter. This show is part of the Airwave Media podcast network. Please visit AirwaveMedia.com to check out other great podcasts like Ben Franklin’s World, Once Upon A Crime, and many more. Learn more about your ad choices. Visit megaphone.fm/adchoices

Kellev Kroached in the shadows behind a chicken coop on a farm outside Tulsa, Oklahoma. It was early April 1932, and it was cold and muddy and dark. Kelly clutched a Thompson submachine gun, but he wasn't familiar with the weapon. The Tommy gun was now the favorite firearm of mobsters and gangsters, but Kelly didn't have much experience with it, and that was about to become a serious problem. Kelly was a retired sheriff with a strong sense of duty. He wanted to return to the community he'd served for so long and catch the most wanted and dangerous criminal in the area.

And the $4,000 reward for the outlaw didn't hurt either. And now, in the dead of night, Kelly was worried. He was worried about his lack of experience with the Tommy gun. He was worried about the two young deputies who were hiding nearby. They had even less experience with law enforcement than he did with a Tommy gun, and he was worried about the man he was here to catch. This criminal, Pretty Boy Floyd, the papers called him, was supposedly a polite bank robber and something of an escape artist

and maybe a cold-blooded killer. And Irv Kelly was out here on this farm in the middle of the night about to spring a trap on a man who could react with deadly violence. With a low mist in the air, Kelly saw a sedan drive up the dirt path that led to the farmhouse. There were two men in the car, and they guided it slowly through the mud. Kelly sprang out of his hiding spot, trained his Tommy gun on the windshield, and yelled for the men to stop and come out with their hands up. A moment later, he knew there would be a shootout.

And a moment after that, he knew he was in trouble. When he squeezed the trigger, nothing happened. From Black Barrel Media, this is Infamous America. I'm your host, Chris Wimmer. In this season, we're telling the story of the 1930s bank robber, Pretty Boy Floyd. This is episode four. Never Surrender. Three days before Christmas, 1931,

an Oklahoma City newspaper printed a reproduction of a circular that the Bowling Green Police Department in Ohio had distributed after patrolman Castner's murder. It had Floyd's mugshot, his fingerprints, and his aliases, Pretty Boy, and Frank Mitchell. It listed his age, 24, his height, 5-7, his hair, dark, his eyes, chestnut. It gave information about the $1,000 reward for his arrest and conviction. It stated that extreme caution should be used when approaching Floyd, alias Mitchell, as he will not hesitate to shoot. The circular was reprinted under the headline, he's Oklahoma's most dangerous outlaw. But Oklahoma's most dangerous outlaw also found time for a reconciliation in the fall of 1931.

While Floyd laid low in Oklahoma after the shootout in Bowling Green that killed Officer Ralph Castner and Floyd's partner, Billy Miller, Floyd reconnected with his ex-wife Ruby. Charles heard rumors that his ex-wife had remarried, and they turned out to be true. Leroy Leonard was a baker and was decent to Ruby and her son, according to Floyd family history.

But that didn't matter when Charles came to town with the idea of getting his family back. No one could say Leonard took it lying down. In fact, quite the argument ensued. But in the end, Ruby and the boy left with Charles Floyd. In and around Floyd's bank robbing tour of Oklahoma with George Birdwell, Floyd found time to create a domestic life that was safe, at least for a short time,

from his criminal endeavors. The reunited family settled in Fort Smith, Arkansas, under the name Hamilton. Charles said he was a traveling salesman when he walked his son, now known as Jackie Hamilton, to the local school. Between heists, Charles experienced a world that might have been if he had taken several different forks in the road. He knew that in the long run, he wouldn't be satisfied with the quiet life, but he relished those family days. He and Ruby and Jackie visited their clans in Oklahoma. Charles took Jackie on fishing trips and to the pictures to see Boris Karloff in Frankenstein.

But even in those blissful days, the real world crept in all. all too easily. Like all big name outlaws, Floyd was linked to tons of crimes he didn't commit. One of the worst happened on January 2nd, 1932, outside Springfield, Missouri. There was suspicion that two of the three criminals known as the Young brothers had returned to visit family. Jennings and Harry Young made names for themselves as car thieves, burglars, and petty criminals. Harry had been in the Missouri State Prison at the same time as Charles. After Henry's release in 1929, the crimes of the Young Brothers grew violent. They were wanted for the murder of a city marshal in a nearby town.

On January 2nd, the local sheriff, acting on a tip, raised a posse, and went to the suspected location of the Young Brothers. A small clearing in front of a farmhouse became a shooting gallery. The cops had more men, but they only had revolvers. The young brothers were armed with a shotgun and a rifle. The outlaws unloaded on the lawmen. The posse was caught out in the open and cut down. Six of the ten men in the posse died in the clearing. The two shooters fled, and in the aftermath, other law enforcement agencies couldn't believe that the carnage had been caused by just two men.

They thought there had to be other accomplices. Pretty Boy Floyd was at the top of their list, and newspapers were happy to run with that theory. It's been called the Young Brothers Massacre, and it was the deadliest gun-related attack on police officers in the 20th century. A few days after the shootout, law enforcement surrounded the young brothers in a farmhouse as they tried to flee to Texas. With no chance for escape this time, one of the brothers yelled, come on in, we're already dead. Then the lawman heard gunshots inside the house. When they entered, they found Harry and Jennings dead of a murder suicide. Charles Floyd had no involvement with the young brothers or their crimes, but the media linked him to the massacre, and not for the

last time. The accusation, plus more robberies, caused the bounty on Floyd's head to double. By February of 1932, Charles had moved his family from Fort Smith, Arkansas to Tulsa, Oklahoma. Charles and his partner George Birdwell continued their spree of robberies. And when Charles' name was linked to the massacre, the state of Oklahoma was finally ready to act. The people in the hills and the back roads may have loved Pretty Boy Floyd, but the acting governor and bank leaders were fed up. The governor offered a $1,000. a reward for the capture of the outlaw, and the state banking association matched it. With $2,000

from Ohio and $2,000 from Oklahoma, the reward for Pretty Boy Floyd was now $4,000. That's the equivalent of 80,000 here in 2021, and that would have been an absolute fortune to the average person who was being crippled by the Great Depression. In a move that Floyd's hero, Jesse James, would have loved, Floyd sat down and penned the letter. Jesse was famous for writing letters to newspapers to defend his actions or to promote his actions, and he may have been the inspiration for Floyd's quick note to the governor that said, Robert Burns, acting governor, you will either withdraw the $1,000 at once or suffer the consequences. No kidding. I have robbed no one but moneyed men. In two sentences, Floyd threatened the governor,

admitted he was a robber, and portrayed himself as a Robin Hood outlaw. It was efficient and flamboyant, and the press loved it. Newspapers dedicated untold column inches to Floyd's missive, but neither the stories nor the threat had any effect on the bounty.

It stayed in place. And now the hunt was on for Pretty Boy Floyd in every big city and small town in Oklahoma. Tulsa police heard rumors that Floyd and Birdwell were in town. The cops scoured their city for the famous robbers. A series of dramatic shootouts took place over a few days on the Tulsa streets. The officers suffered only a few flesh wounds, and they all agreed that they had fought it out with Floyd and Birdwell.

But alas, the robbers escaped every time. It's almost a mortal lock that Floyd and Birdwell were not involved in those robes. run-ins, but they were the most high-profile outlaws in the area. And it didn't take long for the law to hone in on the real location of Pretty Boy Floyd. His family's bungalow was on East Young Street, and it's hard to know exactly what led the police to the house. Maybe the neighbors grew suspicious about the family that spent so much money. Maybe the bullet-riddled car that was found in a ditch outside town held some clues. But whatever did it, two dozen officers descended on the little house in the middle of the night.

In an event that was eerily similar to the Pinkerton attack on Jesse James' home 57 years earlier, the officers hit Floyd's home with tear gas before they charged inside. But once they were in, they found a dry hole. No one was home. Apparently the officers had not been as stealthy as they thought. Earlier in the night, Ruby and young Jackie slipped out of the house and quietly moved through the neighborhood. Floyd and Birdwell supposedly navigated back alleys to avoid the raid. It was another embarrassing missed opportunity, and the media pounced. One headline read, Bandit and Aid strolled among officers. Five heavily armed men said to have let them get away. But the escape was only temporary. Floyd's wife and son were not out of danger. Later that night,

Ruby and Jackie were stopped, questioned, and taken into custody. At first, Jackie recited what seemed to be a well-rehearsed but convincing story of who they were, who his father was, and why they were in Tulsa. Jackie was only seven years old, and he was keeping the family secret. But when officers showed him pictures of Charles Floyd, the man they knew was the infamous bank robber, Jackie finally admitted that the man in the pictures was his father. The game was up, and Ruby confirmed their suspicions. But she made a point of saying that her ex-husband was not guilty of half the stuff in the newspapers, and on that point she was right. The police released Ruby and Jackie. The mother and son piled into their green Ford sedan and fled Tulsa proper. They headed south toward the hamlet of Bixby, which is on the extreme outer edge of the city of Tulsa today,

but was a rural farming community in 1932. They thought they'd found a good place to hide from the law, but they didn't know they'd been followed by former sheriff Irv Kelly. Kelly and his former deputy tailed Ruby's car as she left Tulsa and headed for the farm of Cecil Bennett near Bixby. Some members of Ruby's family worked the land and lived in a small home on the property. It seemed like a safe place to lay low while she and Jackie, waited to reunite with Charles.

Kelly was the retired sheriff of McIntosh County, about 30 miles south of Bixby. His peers knew him to be honest and dedicated. His community was grateful for his leadership in bringing to justice bank robbers and murderers. It had been several years since he wore the badge, but when he offered his services to the state of Oklahoma, officials were thrilled to let an experienced lawmen lead the effort against Pretty Boy Floyd. And Kelly would be thrilled to bring home $4,000 in reward money, as well as stopping a man he saw as a glorified murderer whose Robin Hoodways did little to wash the blood off his hands.

Kelly had heard the stories of Floyd ripping up loans for poor farmers when he robbed banks so that the farmers would never have to repay the deaths. He'd heard about the polite thief using money from his heists to buy Thanksgiving dinners for sharecroppers in need. and Kelly wasn't impressed. Floyd was still a robber and a killer, and that's all that mattered to Kelly. He assumed Pretty Boy Floyd would eventually try to make contact with his ex-wife and son, so Kelly gathered a small posse and staked out the farm of Cecil Bennett.

Around the clock, they weathered the cold spring nights and watched the dirt roads around the farm. On April 9, 1932, it looked like Kelly hit the night. peter. He had been tipped off by a local that the Bennetts were expecting Charles Floyd for the weekend. After dark, Kelly took a position behind a chicken coop near a road that led to the farmhouse. He began a long, cold wait in the mud and muck. He had two new deputies stationed nearby, but they were recent recruits and inexperienced. More officers were stationed a quarter mile away. Just past midnight, a car drove slow. slowly down the muddy road that led to the Bennett farm. There were two men inside. As the car

neared the chicken coop, Kelly left his hiding spot and confronted the driver and the passenger, Pretty Boy Floyd and George Birdwell. If Kelly tried to pull the trigger at that moment, it didn't work. Floyd jumped out of the car and opened fire. Kelly fixed the problem with the gun, whatever it was, and squeezed the trigger. The Tommy gun roared to life, but most of the bullet plowed straight into the ground at Kelly's feet. Two, however, found their marks. One hit Floyd in the leg and the other hit him in the foot. But by that point, Floyd had already found his mark as well. He shot Irv Kelly and killed the retired sheriff on the spot. George Birdwell helped Floyd back into the car and they sped away. They raced to the farm of Floyd's brother Bradley

while the rest of the posse and the two deputies hurried to the site of the shootout. At the Bennett Farm, the two new deputies and the rest of the lawmen stood over the body of Irv Kelly. The deputies hadn't been able to or were too scared to help. No one saw the direction of the getaway or knew where to look next. The manhunt was back to square one. Meanwhile, 90 miles away at Bradley Floyd's Farm near Seminole, Oklahoma, Bradley asked a local doctor to help his brother. The doctor treated Charles' gunshot wounds and promised to keep his mouth shut.

He was a loyal friend and he could be trusted. Two days after the shootout, thousands attended Irv Kelly's funeral in McIntosh County. And some time later, while still on the run, Pretty Boy Floyd admitted the truth of the night to a reporter. He said, Irv Kelly nearly got me. There was only one thing to do. It was either him or me, so I let him have it. A few weeks after the Bixby shootout, Charles Floyd and George Birdwell were back at the bank.

The duo hit one in Stonewall, Oklahoma. They got away with a measly $600 and took two bank employees with them for cover as they sped out of town. They released the hostages when the coast was clear, and soon stopped a local teenager on a motorcycle, Estelle Henson, and insisted that he joined them. Somewhere between Stonewall and Ada, Oklahoma, the two bandits and the boy hid the car and made camp. While the amount of money didn't make headlines,

the fact that the uncatchable Pretty Boy Floyd had pulled off the robbery so soon after killing Kelly incensed local lawmen, federal lawmen, and state bank officials. The Oklahoma Bankers Association had paid rewards for over 200 robbers who had been killed or captured. More than 90% of the banks that were robbed in Oklahoma were small rural banks like the one in Stonewall. And the name synonymous with small town heists

was Pretty Boy Floyd. So it was no surprise that the manhunt that followed the Stonewall job was massive and exhaustive. For one of the first times in law enforcement history, officers hunted a wanted man from the sky. Famous aviator Wiley Post, the first pilot to fly solo around the world, led a team of airmen who scoured the wide-open spaces of central Oklahoma in an attempt to spot Floyd and Birdwell. While the airborne investigation made for good newspaper stories, the search yielded nothing. With no capture to report, the pretty boy-related headlines moved to young Estelle Henson.

After the teenager spent a night on the run with the outlaws, he was released unharmed and without incident. The 18-year-old was all too willing to share the tale of his kidnapping. In an article for the United Press, Henson said, I spent 13 hours as the captive of Pretty Boy Floyd and George Birdwell and found them to be good fellows. Henson also claimed that there was a point when Birdwell slept and Floyd worked out a jam in his machine. gun. There was a pistol within Henson's reach, and he thought he could have taken down the two outlaws. But he confessed in the article, I wouldn't shoot one of them for $10,000, and I had the chance, or thought I did. As the two outlaws eluded police, the summer of 1932 was full of

Pretty Boy Floyd sightings. Charles Floyd seemed to be everywhere, but in reality, he and Birdwell were still in Oklahoma. When the two men held up a bank in Salasaw right outside Floyd's hometown, the scene was more of a homecoming than a heist. Floyd greeted friends, told nearby shopkeepers what he was about to do, and kindly suggested that they stay away from the phones. The two outlaws left the bank with just over $2,500 and an employee to ride the sideboards of the car for cover. But the cover of hostages wasn't needed. Local law enforcement gave a cursory chase, but they knew it was pointless. Charles Floyd could find safe haven at any farm or backwoods moonshine shack for 50 miles in all directions.

Once he was out of town, he was gone. In November 1932, former New York Governor Franklin Delano Roosevelt defeated Herbert Hoover to become the 32nd President of the United States. The nation made the election a referendum on Hoover's face. and the need for new leadership if it was going to survive the Great Depression. But the hopefulness of Roosevelt's election was tempered by the realities of the economic crisis that still gripped the country. The southern plains were right in the middle of the Dust Bowl years. Crops failed, severe drought crippled the region, and vicious dust storms rolled across

the landscape like signs of a biblical apocalypse. That November, Charles Floyd robbed the bank. in Salasaw again, and then did something he'd never done before. He granted an interview to a reporter. Vivian Brown stood beside a blue sedan in the shade of a pecan tree. A man in a dark coat had picked her up in Muskogee and driven her out to this meadow. He said nothing during the trip, and the silence was unnerving. He parked next to another car, and now Vivian stood outside, waiting for the man in the other car to exit. She'd worked hard for this meeting.

She was a local in eastern Oklahoma. She knew the area, the people, the habits, the traditions, and the likes and dislikes. She was an educated woman who attended teachers' college and had dreams of becoming a reporter, so she started researching the most famous outlaw in Oklahoma history. Vivian followed his exploits. She took notes and formed a profile. Slowly she won the confidence of those close to him, and eventually he agreed to meet her. And not just that, he agreed to go on the record and give the only interview of his short but unforgettable crime wave through the heartland.

When the outlaw stepped out of his car and walked up to her, she thought to herself, he looked like a country boy gone to town. He was stalky with slicked back hair and an easy smile. He strode up to her and said plainly, I'm Charles Flores. Floyd. Over the course of their conversation, Vivian said Floyd regaled her with tales of over 60 bank robberies and wild car chases and lucky escapes. He said he'd stolen more than $500,000, which would be more than $10 million today. It was a healthy exaggeration, but she let him talk. He confessed that he regretted the shootout with retired sheriff Irv Kelly seven months earlier. Floyd viewed it as a

him or me situation. He praised the people of rural Oklahoma, Arkansas, and Missouri who showed him kindness. He hoped he never scared anyone he hadn't needed to. He bragged about his daring escape from the train that was bound for the Ohio

State Prison. He played down the nickname he never liked, saying, that name Pretty Boy is all a joke anyway. These folks here call me Charles or Charlie. He hoped his family hadn't suffered because of his lawless ways, and more than anything, he hoped that the life he'd been driven to hadn't scarred young Jackie too much.

Yes, there have been times I wished I was out of it, Charles Floyd said, but I'll never surrender. It took two years for Vivian Brown's article to get published. By the time it did, the man who hated the nickname Pretty Boy had proven conclusively that he would never surrender. As 1932 wound down, Charles Floyd had about a year and a half to live. He would have to take his life on the run to a whole new level because federal law enforcement was about to take a giant leap forward. J. Edgar Hoover, head of the Bureau of Investigation, was taking the gloves off. So were officials in Washington.

The violence of the gangster era became more shocking by the day. And the event that jump started the no-holds-barred philosophy of lawmen was the Kansas City Massacre. Next time on Infamous America, machine gun fire rips through the parking lot of Union Station in Kansas City. Pretty Boy Floyd may or may not have been involved. Then he loses his bank-robbing partner and flees across the country as the feds mobilized to start bringing down all the famous outlaws of the era. That's next week on Infamous America. Members of our Black Barrel Plus program don't have to wait week to week for new episodes. They receive the entire season to binge all at once with no commercials,

and they also receive exclusive bonus episodes. Sign up now through the link in the show notes or on our website, blackbarrelmedia.com. Memberships begin at just $5 per month. This season was researched and written by Jamie Lyko, original music by Rob Ballier. I'm your co-writer, host and producer, Chris Wimmer. Find us at our website, blackbarrelmedia.com, or on our social media channels. We're BlackBarrel Media on Facebook and Instagram and B-Beryl Media on Twitter.

And you can stream all our episodes on YouTube. Just search for Infamous America Podcast. This show is part of the Airwave Media Podcast Network. Please visit airwavemedia.com to check out other great podcasts like Ben Franklin's World, Once Upon a Crime and many more. Thanks for listening.