Infamous America - PRETTY BOY FLOYD Ep. 1 | “The Short Road”

Episode Date: January 26, 2022

Charles Arthur Floyd grows up on his father’s farm in Oklahoma and travels the southern plains as a field hand during harvest season. But he quickly grows tired of life on the farm. He participates in a small robbery, and then travels to the big city of St. Louis to lead his first real heist. After that, he’s hooked. Despite his new marriage and his newborn son, he can never go back to the quiet life. Try Headspace and receive one month free! Join here Headspace.com/infamous Check out the Jordan Harbinger show today! jordanharbinger.com/start 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

Ellen Conkel cleared the dishes in her kitchen as a man sat on her porch reading the local newspaper. He had come down Spruce Vale Road and found her cleaning her smokehouse. He made it clear he was no vagabond who wandered too far from the nearest shanty town or Hooverville. He offered her money for a meal and she heated some spare ribs. He said he'd been out hunting with his brother and gotten lost. But she'd never seen a man go hunting in a suit. This guy was well-dressed, but covered in mud, and he didn't have a rifle, which she expected to see if he'd actually been out hunting.

He was a young man, maybe in his early 30s, plain-spoken, but very polite. She could tell he'd been raised to respect his neighbors, revere his kin, and never look down on his fellow man. He needed food, but felt poorly that he was interrupting her day. He had eaten, been complimentary, and, and left money under his dinner plate that Mrs. Conkel did her best to refuse, but he insisted. And when he asked about the automobile by the barn, she had told him it was her brothers, and yes, he might be able to catch a ride partway into town.

Ellen Conkel felt, as she cleared that dinner plate and coffee mug, that she had done right by one of the thousands of good people who had been subjected to strife, joblessness, and homelessness, because the winds of the world had been done, blowing against them for so many years now. Little did she know that in the not too distant future, she would be posing for pictures with those same dishes and they would become family heirlooms. Little did she know that in a few hours, that well-dressed man would be sprinting toward the woods as an arsenal of Winchester rifles, shotguns, and handguns fired at him. The man had introduced himself as Charles, but his family called him Charlie or even Charlie.

chalk. Sometimes he was known as the Robin Hood of the Cookson Hills. More often he was called a bank robber, an outlaw, a killer, and finally, public enemy number one. But history knows him by the nickname he always hated. Pretty boy Floyd. My relentless sleep problems have always come from an overactive mind. I lay in bed at night with my mind racing from one thing to another, and then of course I have a brainstorm about something new. That lights the fire and then I'm in real trouble. To calm my mind, the only things that have ever worked with any consistency are sleep gummies. Sleepy time advanced gummies from mood.com come in various combinations of THC, CBD, and CBN. So you can get something that's very low in THC, but higher in CBD, which helps turn off the stress.

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From Black Barrel Media, this is Infamous America. I'm your host, Chris Wimmer. And this season we're telling the story of 1930s bank robber, Pretty Boy Floyd. This is episode one, A Short Road. There's little in the childhood of Charles Arthur Floyd that would make you think he was destined for a short but dynamic life of crime. Unlike his outlaw contemporaries, Floyd's childhood in early teenage years were relatively mundane.

John Dillinger, for instance, was born to a stern, sometimes cruel father with whom Dillinger had had a combative relationship. He was a troubled kid, capable of violence and seen as a bully. He was arrested for auto theft and dishonorably discharged from the merchant marines all before he was 20 years old. Similarly, Lester Gillis, known as Babyface Nelson, had already spent a year and a half in a reform school and on a work farm before he was 15. Charles Floyd's life was full of hard work and his father wasn't the most affectionate person on earth, but it wasn't a violent or abusive situation. Charles was born to Walter Floyd and his wife Maybe on February 4th, 1904, in northwest Georgia, and he was the fourth of nine children. When Charles was seven, the family left the south

and headed west. Until 1907, the state of Oklahoma was known as Indian territory. Tribal nations that had once ruled the southeast had been forcibly removed in a tragic event called the Trail of Tears. The place names reflected the tribes that had once moved against their will, Seminole County, Choktaw County, and Sequoia County, where Walter Floyd eventually settled his family. They lived in the small town of Aitans, 10 miles from Salmon, the county seat of Sequoia. It was a beautiful and fertile region, just south of the Cuxson Hills, and the Floyds would be surrounded by Walter's family as well as Mamie's mother and father. Walter was a stern but fair man, a hard worker who valued discipline and his family's status in the community.

Mamie was a woman of faith, a lifelong churchgoer who converted her husband later in life. Along with his family, Charles rarely missed church services on Sunday. For most of Charles' youth, the family made their money in cotton, but also maintained an almost entirely self-sufficient farm. Charles thrived. He was a field hand on the family farm before he hit his teenage years, and though he wasn't necessarily big for his age, he had the strong, stout look of a boy who had grown up toiling in the fields. He was formidable and excelled at sports. He wasn't overly aggressive, but he was not one to back down from a confrontation either. Charles had a strong sense of fairness, and he was often quick to defend someone smaller,

even if it cost him. As a boy, he nearly lost an eye in a fight when he refused to back down even though he was outnumbered. While from a pious family, Charles, Charles' sense of right and wrong was shaped by the frontier he grew up in. The second decade of the 20th century was not that far removed from the days of the Wild West. And while the stories of chivalric cowboys and steady-handed sheriffs were fine, the legends of the outlaws were the ones that resonated the most. From the budding cities to the sleepy hamlets, the exploits of the Dalton gang were still fresh in the memories of many.

It wasn't unusual to find someone who clasinated. claimed to have sipped cheap whiskey in some Arizona Territory Saloon with Billy the Kid. Butch Cassidy and the Sundance Kid were killed in Bolivia just three years before the Floyd family moved to Oklahoma. In eastern Oklahoma, they still followed the exploits of Henry Starr, who was born in Muskogee County and was said to have robbed more banks than any man alive. But for young Charles Floyd, there was one outlaw who rose above the rest, Jesse James. A famous folk song about Jesse started making the rounds in 1919 when Charles was 15 years old. It was a favorite around campfires, at country dances, and in illicit taverns across the state.

It celebrated the James Younger gang's Glendale train robbery, and had lamented Jesse's death at the hands of a young man he once trusted, Robert Ford. But more than anything, the song made the outlaw into an American Robin Hood. Charles loved the song. He loved the stories of Jesse only robbing soft-handed bankers and outwitting dumbfounded Pinkertons. The idea of being forced into a life on the wrong side of the law

struck a chord with the adolescent Charles Floyd. Of course, the truth was that Jesse wasn't forced into a life of crime and he certainly wasn't a Robin Hood figure who stole from the rich and gave to the poor. But Charles Floyd didn't know that. somewhat ironically, Charles Floyd would become that Robin Hood figure for the people in Oklahoma. And in the end, he too would have a folk song written about him.

By 1918, the war to end all wars had ended. And though the death toll in the United States was much less than in Europe, there was still 117,000 Americans, including more than 1,000 from Oklahoma, who never returned home. The Floyds were spared. Charles' older brother Bradley enlisted but never left Fort Bliss in El Paso. He returned to his family and the farming community of Sequoia County. The war was over, but it quickly became evident that it would continue to affect rural America.

Coal and textile prices dropped, leaving farmers like the Floyd's with cotton they couldn't sell. Farmers were left with little assistance from their government, and the distrust of the banking system had begun long before any American boosts. hit the ground in France. The state of the tenant farmer, young, poor, bound by high rents, and shouldering significant debt due to immoral systems of credit, had been bleak and was growing more so. In Charles Floyd's community, there was a general mistrust of those who had the power and controlled the money. It was clear to Charles that he was growing up in a world of halves and have-nots. He started to realize that he didn't belong in the first group, and he certainly didn't want to stay in the second.

So, sometime after he turned 16, Charles left home and headed west out of Sequoia County and over the Cookson Hills. He followed the harvest, working as a farm hand, picking and shucking corn, threshing wheat or baling hay. He was a fit young man, and while he wanted to see more of the world, the respect for a hard day's work. instilled in him by his father, never left him. No job was beneath him. Except for the few dollars he sent back home to his mother, the Floyd family heard little from Charles in the first few years as he made his way across the plains. He worked in cornfields and wheat fields during the day and spent his evenings relishing a jar of moonshine and playing dice or cards. But the life of a nomadic field hand grew tiresome. Somewhere along the way from field to field and harvesting,

to harvest, the young man found himself in the city, specifically, Wichita, Kansas. It had once been a cow town along the Chisholm Trail that was home to Wyatt Earp. Then the population and wealth grew after oil was discovered. And by the time Charles Floyd arrived in Wichita, one of America's greatest mistakes had taken effect. The Volstead Act was now the law of the land, and it banned the manufacture, sail, transport, and consumption of alcohol. It was commonly known as Prohibition.

As in most cities, prohibition led directly to the growth of organized crime in Wichita. John Callahan, an Irishman in his 50s, was the dominant figure in the city's underworld. He was a bank robber and one of the more infamous dealers of stolen goods west of the Mississippi,

and he was also a bootleggar. Callahan was known to develop young men who were keen on making easy money, and it's thought that he may have made Charles Floyd one of his acolytes. Working for Callahan, Charles may have encountered a gangster named Frank Nash, a criminal who would unintentionally have a profound impact on Floyd's life. Here in Kansas, crisscrossing the state for Callahan in a car stocked with illegal spirits, historians believe Charles got his first taste of fast but dangerous money. Charles discovered that he was meant for this life.

Not that of a dirt farmer. In early 1922, Charles went home to Sequoia County. It could be that the action got too hot up in Wichita, or maybe he was just homesick. But when he returned to his hometown of Aiken's, he had tales to tell. When the young ones were in bed and the whiskey, now illegal, had been poured, Charles told stories of his life on the open road. He talked about the big city and the world that was becoming the roaring 20s. His family could tell that his travels changed him.

Though still good-natured, well-mannered, and generous, there was a glint in his eye when he spoke of his days in Wichita, a glint that convinced him he wasn't done with that life. Charles went back to work on his father's farm, but he found time to play cards, shoot dice, and enjoy an impromptu party in a barn or in the woods, where moonshine or chalk beer could be enjoyed. Charles was so partial to the latter,

which was a mix of barley, hops, berries, and alcohol that was named for the Chokta tribe that he earned the nickname Chalk. As he spent more time in Aitken's, his restlessness and rambunctious spirit came out. Ironically, it was in his small hometown, not the big city, where Charles would get into his first real trouble that would have real consequences.

On a cool morning in May, a shopkeeper in Aiken's opened for business. The unseasonal chill made the front door stick, and he took notice of the chipping paint on the door jam. Inside, it was colder than usual. His store tended to lock in the dry heat of the afternoons when he closed up at night, so this morning's temperature was an instant sign that something was different.

He discovered a breeze coming in from the side of the store. It was down there by the fountain drinks, and the space that doubled as a post office. When the shopkeeper followed the breeze, he found a window with a busted latch. Paint chips were stripped from the wood, and it was clear the window had been forced open from the outside. Quickly, the shopkeeper took inventory.

The registers were okay. So was the safe where he kept pending bank deposits. His shelves seemed fine. Everything from rifle ammo to laudanum seemed undisturbed. But over by the area where he charged for stamps and collected small packages to be shipped to Tulsa or Fort Smith, Arkansas, there should have been several jars of loose change. They were gone. He guessed that they held a total of about $3.50.

Of all the things in his shop, the thieves took $3.5 worth of coins, mostly pennies. The shopkeeper reported the break-in and the robbery, and news of the Great Aiken's Daycare. penny heist spread quickly. $3.50 is the equivalent of about $57 today, and that would certainly have gone a long way in the early 1920s. But the amount wasn't the most serious problem, nor was the breaking and entering. It was the fact that the money had been stolen from a place that was an official post office. That made it a federal crime.

Local deputies used bloodhounds to track the burglars, but it didn't work. An investigator came over from Muskogee and started an investigation. It led to 21-year-old Harold Franks and his accomplice, Charles Floyd. When questioned, Franks rolled over immediately and claimed Charles was the mastermind. Charles maintained his innocence. His father, Walter, stepped in and did something that was totally against his nature. Maybe it was because he sensed a change in Charles and worried that a small, crime could lead to bigger crimes. Maybe he was simply trying to keep his family name from being

tarnished. But Walter Floyd lied to federal agents and provided his son an alibi. He told them Charles was at home, fast asleep, and resting up for another long day on the farm. The case lingered over Charles, but he was eventually acquitted. More than likely, it lingered over Charles' relationship with his father for much longer. And while the relationship between Charles and his father slowly soured, another relationship began. In early 1923, Charles Floyd met Ruby Hardgraves, a farmer's daughter with brown eyes and Cherokee blood.

And at least for a little while, it seemed like Charles might choose a quiet, rural life instead of the high-octane life of an outlaw. Charles was a handsome young man with dark hair. intense eyes and an infectious personality. It surprised no one that women seemed to like him as much as he liked them. But while flings and fun had entertained him up to this point, Ruby changed everything.

Whenever Charles wasn't in the fields, they were at each other's sides. With inside of church folks, they courted in their regularly accepted manner. But out past the tree lines or in any place of solitude, the passion of their relationship took over. They were already well acquainted with each other by the summer of 1924, and neither was shocked when Ruby discovered she was pregnant.

The baby was due around Christmas. The young lovers were happy to become a young married couple. It was a humble service, but a great celebration. Charles even felt his father's coldness thaw a bit at the prospect of another grandchild. Charles Dempsey Floyd was born on December. December 29th. His first name honored Charles' grandfather, and his middle name honored the heavyweight champion of the world, Jack Dempsey, one of Charles' heroes. Many people believe that the pride Charles took in his baby would cause him to settle into rural life like

everyone else. It looked like his desire for adventure and the big city was waning. But the realities of the world remained. There was little chance to better his life or that of his new family in Aiken's or Salasaw. The world still seemed rigged for the rich, and Charles could never forget the notion that beyond the Cooks and Hills, there was easy money to be had for a man who was willing to risk it.

In late summer, 1925, Charles broke the news to his new wife that he would head back out on the road to follow the harvest as he had in the years before he met her. He would send money home, and hopefully they could use it to save up for a better life. and, in theory, he'd be back after the busy season. But in truth, he would be gone long after all the corn had been picked and the hay had been stored.

Before leaving town, Charles Floyd, 21 years old, gathered a few jugs of moonshine. He headed down a dirt road in Aiken's to the home of a well-known bootleggar. He offered the shine and asked the man if he was open to a trade. The man reached into a desk drawer. and pulled out something that was wrapped in a white handkerchief. He asked Charles if he was sure. Charles put the jugs down, nodded to them and said, Here, you can take this.

I'm tired of trying to make a living with it. Charles picked up the bundle from the bootlegger and said, I'm going to give this a try. In the handkerchief was an old, but clean and polished, 44 caliber revolver with pearl handles. Charles Floyd was hitting the road, but he wasn't going to pick cotton. Just before leaving town, Charles met a man named Fred Hilderbrand.

Fred would be a good traveling companion and a willing accomplice in the adventure to come. They hitchhiked and rode the rails to St. Louis, Missouri. Before Prohibition, one of the major industries in St. Louis was the production of beer. But now, manufacturing dominated the city. With no interest in sewing ladies undergarments or making automotive parts, Charles and Hildebrand went to work in another way. They were almost certainly responsible for a string of Kroger grocery robberies in and around St. Louis that summer of 1925.

The halls weren't overwhelming, probably around $500 or $600 in total. But they got noticed and began to think bigger. robbing an individual store could get them a couple hundred bucks. Robbing the corporate headquarters, that could get them thousands. For Charles Floyd, it proved to be a short road from farmhand to bootlegger to small-time thief to full-blown robber. Joe sat in a stolen Cadillac V8 outside the regional headquarters for Kroger Grocery and Bakery on the corner of Tiffany and Vista in St. Louis. It was just before 1 p.m. on the afternoon of September 11th, 1925.

He knew that an armored car from a local bank would arrive with the payroll money for hundreds of employees. If the math was right, that would mean over $10,000 in cash. Joe's last name starts with an H, but no one can agree on the spelling and it's impossible to pronounce anyway, so he's just going to be Joe from now on. Joe owned a small market, and he recently rented rooms above it to two men who had come up from Oklahoma. One was named Fred, and the other sometimes called himself Floyd Schmidt, and other times Charles. They had approached Joe about being the third man in a robbery. With Joe in the Cadillac were his tenants, Fred and Floyd.

Joe thought Fred Hildebrand was the anxious type. Allegedly, while robbing an electric company, Fred had pistol-wipped an executive who moved too slow. But Fred had been savvy enough to successfully shoot his way out when seemingly surrounded by the police. Floyd Schmidt, or Charles, or whatever his real name was, was the opposite. He sat in the front seat, holding the pearl-handled revolver in such a calm way that Joe thought he might fall asleep. Floyd was a country boy for sure, but he certainly didn't seem awed by the big city, or the prospect of the robbery that was about to begin. Fred had applied for a job at Kroger and failed to get it,

but in the process, he observed the drop-off of the payroll money. A bank car pulled up, someone walked inside with the money and handed it to a clerk, and there was very little security. The plan was to wait until the bank car left. Then go in, flash their weapons, take the cash, and be out in a matter of minutes. Just after one o'clock, the three men in the stolen Cadillac watched the bank car pull away. The money had been dropped off, and it was time to go. Joe started the engine.

Charles spun the barrel of his gun. Hildebrand pumped a shell into a sawed-off shotgun. They hoped there would be no need for shooting, but they were ready just in case. Joe moved the car into a better position for the getaway. He parked, they stepped out, and walked across the street. They looked nondescript. They could be plumbers or delivery drivers or janitors, and they made no effort to cover their faces.

They walked into the building and hustled up a short staircase to the cashier's office. They were in plain sight of dozens of Kroger employees, none of whom seemed to notice that two of the three were carrying guns. As the robbers reached the top of the stairs, they could see into the cashier's office through a window. The paymaster was already dividing up the cash for payday. The general manager watched and chatted with a secretary. Charles got to the door first. He pulled it open for Fred and Joe, and they rushed inside.

Charles followed and shut the door behind them. He turned and aimed his revolver at the man who was counting the money. Fred leveled the shotgun at the other clerk in the room and said, All we want is the payroll money. Don't scream, or we will have to kill you. Next time on Infamous America, it's the conclusion of the first major robbery of Pretty Boy Floyd's career, and then the aftermath, and then one painful event after another,

as the roaring 20s come to a close and the Great Depression begins. 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 episode 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 Lyco, original music by Rob Valier.

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-Barrel 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, England's world, Once Upon a Crime, and many more. Thanks for listening.