Infamous America - PRETTY BOY FLOYD Ep. 2 | “Hard Time”

Episode Date: February 2, 2022

Charles Floyd might like the exciting life of an outlaw, but he’s not good at it yet. An arrest leads to a prison sentence and then a divorce from his wife. Floyd begins to establish himself in the Kansas City criminal underworld, but then a family tragedy calls him home. 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

Walter Floyd stood in the doorway of his Aiken store, having a nip of moonshine to steal himself against the cold of the morning. It was unseasonably cold, even for mid-November out on the plains. Walter had mined boxite for a living. He'd been a fireman on the western and Atlantic railroad between Chattanooga and Atlanta, and he'd picked cotton, so much cotton. But with prices what they were, starting a store had been a shrewd move. He carried grain and farming supplies and normal sundries that folks needed to avoid a trip into the larger town of Salasaw. The store wasn't lavish, but Walter wanted something for his family to fall back on, and there was a lot of family to think about.

His children had given him a bunch of grandchildren, and most of his family members were within a few hours by car, except one, his son Charles Arthur. Walter worried about the young man as much as he begrudged him. And maybe if Walter hadn't been thinking about his son, or if the store had been busier, or if he'd had one less slug of liquor, he may not have let his temper get the best of him when he saw the shopkeeper across the street, Jim Mills, arrive for work. Walter and Mills had a running dispute over mills collecting salvaged wood from a local rundown gin mill. The owners, after clearing out the equipment, had promised anything that was left to Walter Floyd. But Mills had taken shingles and beams and two-by-fours and was now selling them in his shop.

Until that point, the feud had yet to escalate beyond some hot words and spiteful glares. This morning, all that changed. Walter crossed the street purposefully, walked up the steps of Mills' store, and let loose a string of accusations and expletives that he hoped his pious wife couldn't hear at his own store across the street. Mills lashed back. Walter fumed. He stormed back toward his shop, not really sure what his next move was. Then he heard a commotion behind him at Mills store. Someone yelled, wait, Jim, wait. Walter heard stomping steps in the dirt road. He turned to see Jim Mills aiming a sawed-off shotgun, and there was nothing in Jim's eyes that made Walter believe the gun was just for show.

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Pretty Boy Floyd. This is episode two, hard time. The St. Louis Kroger robbery began perfectly. Charles, Fred, and Joe had stolen a Cadillac from a chauffeur in the middle of the city on the morning of the heist. It was fast, and if all went well, they could ditch it and move the money and the guns into Joe's car, which was stashed a few miles from the headquarters. The delivery of the payroll money was right on time. After the drop-off, there was zero security for the money. Charles, Fred, and Joe had raised no suspicion as they entered the building and made their way to the cashier's office.

The robbers barged into the office where the employees counted the money. Floyd held a 44 caliber revolver. Fred had a shotgun. They demanded the money and threatened to kill the employees if their demands weren't met. The Kroger employees complied without resistance.

Within minutes, the men had the money and were back outside. The rest of the employees in the building were oblivious. But the general man, manager and a Kroger driver saw the Cadillac speed away from the building. While the GM waited for the authorities to arrive, the driver followed Charles and company through the streets of St. Louis. At some point, the driver came upon a patrolman, and together

they continued the pursuit. As the robbers dropped Joe off at his car, the Kroger driver and the officer confronted them. Fred Hildebrand jumped out of the Cadillac and opened fire. Joe fled back to his market, and Floyd and Hildebrand were able to elude, capture, and ditch the stolen car. They had been sharp and professional. The job was called sensational in the newspapers, and news of the job was a headline across the country. The bandits stole nearly $12,000 in cash. Charles had his first taste of a big heist, a shootout, and a high-speed getaway. At times, the newspapers referred to him as Floyd Schmidt, but they were also printing a new name.

When interviewed, the Kroger Paymaster told the police and reporters that one of the fellows who robbed them was a mere boy, a pretty boy with apple cheeks. While some legends say Charles received a nickname later in life working in the Seminole County oil fields, others tell of an infamous madam in Kansas City who gave him the moniker. But in the months after the Kroger robbery, newspapers had already dubbed him Charles Pretty Boy Floyd. While there are competing beliefs about where the name started, two things aren't up for debate. One, the nickname was going to stick. And two, Floyd would always hate it. Also not up for debate was that Floyd and Fred Hildebrand were not ready to handle their success.

After meeting up with Joe and dividing the money, Floyd and Hildebrand decided to skip town for a while. They headed back down to Salasaw, Oklahoma, but not before making a few stops. They got shaves and haircuts and bought new suits, and they also bought brand-new stew-de-bakers. Floyd, who had left town with virtually nothing to his name, came back into Sequoia County looking like a different man.

As a result, he and Hildebrand barely had time to throw back a job, jar of moonshine before they caught the attention of local law enforcement. The presence of two brand new cars on the dusty streets of Salasaw was enough to raise a deputy's eyebrow. And the cars weren't just any Studebaker's. They were Studebaker Big Sixes, the vehicle of choice for bootleggers because they could drive 80 miles per hour. In no time at all, the deputy sheriff and chief of police were asking Floyd and Hildebrand questions. The deputy sheriff and the police chief both knew the Floyd family, and they recognized a young man they'd once called chalk. Floyd and Hildebrand exited the car when asked.

They may have had a pistol or two, but they had left the shotguns in St. Louis. The officers appreciated the men's cooperation and their friendliness, but they still had their suspicions. How was Charles Floyd, a young husband and father, who had allegedly left town to follow the harvest, driving a brand new $3,000 car. Believing he had nothing to hide, Charles was more than happy to let the officer search the vehicle. But when the police chief checked the back seat, he found several thousand dollars in cash.

Having that much money was not a crime, but some of the stacks of bills were in wrappers stamped Tower Grove Bank of St. Louis, the bank that provided the payroll to Kroger Regional Headquarters. Floyd and Hildebrand hadn't bothered to take off the rappers. The chief and the deputy didn't know it yet, but the two sharp-dressed young men in front of them were wanted for robbery in Missouri. The officers took the young men into custody while they made some calls about the money. It was not a difficult mystery to solve. When the Muskogee Daily News reported the capture of the men,

they referred to Charles as, the son of one of the most respected farmers in the Aiken's Oklahoma community. Certainly Walter Floyd felt that the family reputation had been tarnished, as he, his family, and his friends watched Charles shackled and shipped back to St. Louis for questioning. Ruby watched the scene holding young Charles Dempsey. She was barely able to set eyes on her husband before he was taken away. She wondered how old the baby would be when he saw his dad. daddy again. In St. Louis, the robbers were photographed by police. The office workers from the robbery

looked at the photos of Charles Floyd and Fred Hildebrand and positively identified them as the culprits. Charles stonewalled the authorities and claimed he wasn't involved, though he couldn't explain why he had money from the bank that had supplied the payroll for Kroger's. Hildebrand flipped quickly, hoping for leniency with his cooperation. He identified Charles and Joe as his fellow assailants. The St. Louis PD stormed Joe's apartment and found over $2,000 in cash, and Joe confessed immediately. Charles spent weeks in a cell maintaining his innocence until finally confessing his involvement. In November 1925, two months after the robbery, he was sentenced to five years in the Missouri State Prison in Jefferson City.

Charles was about to learn about the less glamorous side of the outlaw life. Hard time. Known as the Old Jeff, the prison was a fortress that sat on the banks of the Mississippi River. While the prison system in America had improved since reconstruction, just because inmates weren't being strung up by their thumbs or waterboarded, did not mean that American prisons were houses of rehabilitation. Charles Floyd, now known as inmate number 293, 0978, faced overcrowding, malnutrition, abusive guards, and a hierarchy among inmates that

devoured the weak and hardened the strong to continue their lives of crime if they ever got out. For the majority of his time in prison, Charles kept his head down. The guards and the warden certainly knew his name, but besides a random dust-up with a guard or a stolen potato or two, the necessary ingredient in prison moonshine, Charles was regarded as an above-average prisoner, with an intellect and street-smarts better than his fellow convicts. Most of all, the usually gregarious Charles Floyd learned that while doing a prison stint,

it was better to talk less and listen more. As Charles washed dishes in the kitchen at the old Jeff, or worked as a plumber's assistant, or toiled on the prison's farm, the world continued to turn and the 20s continued to roar. Industry grew and technological advancements tugged the world forward. In 1927, Charles Lindbergg completed the first solo transatlantic flight from New York to Paris. It had been just 24 years since the Wright brothers flew a lighter-than-air craft just 10 feet off the ground for barely a minute in Kitty Hawk, North Carolina.

Linberg received a ticker tape parade through the canyon of heroes in New York City and became one of the most famous men in the world. America became obsessed with the promise of aviation, and the progress didn't stop there. Philo Farnsworth transmitted an image of a straight line from one monitor to another, and television was born. Al Jolson starred in a film called The Jazz Singer. He implored the audience to, wait a minute, because they hadn't heard nothing yet. And for the first time, the audience actually heard the words. The talking picture had arrived.

Organized and not so organized crime continued to flourish, even though proponents of prohibition promised the American people that banning alcohol would end lawlessness. Bank robberies were on the rise in rural America. Paul Jaworski and his flathead gang made news in March of 1927, when they committed the first recorded robbery of an armed car, making off with $104,000. In Chicago, less than a year before Charles' release,

Al Capone ordered a hit on members of the Bugs Moran gang. Disguised as police officers, Capone's men lined up the Moran men in a garage in Lincoln Park and gunned them down. The St. Valentine's Day massacre would become one of the most sensational crimes of the decade. But the most shocking news that Charles received during his stint in the old Jeff came just weeks before he was paroled in March 1929. His wife Ruby filed for divorce.

Charles understood. He didn't fight it, and he granted Ruby full custody of four-year-old Charles Dempsey. Maybe if he still had his family, Charles could have returned to Oklahoma and changed his ways. But without Ruby and Charles Dempsey, he took some advice from a fellow convent. and headed to Kansas City. The newly free 25-year-old received a rude welcome. Two days after he left prison, he was arrested and held for an unnamed crime.

Although he was quickly released, law enforcement made it clear. Kansas City didn't need any more young men with zero prospects in a rap sheet, though that was a bit ironic. In Kansas City, the line between lawmen and criminal was thin. The man who raised,

ran the political machine that ran Kansas City was Tom Pendergast. He was so powerful in those days that some people referred to Kansas City as Tom's town. Enforcement of Tom's commands was provided by a gangster named John Lotzia. A bootleger in Lonshark, Lotzia organized and delivered elections for Pendergast by whatever means necessary. In return, Lotzia benefited from Pendergast's political influence. So firm was their grasp on Kansas City that any job planned within the city limits was expected to be cleared by Lotzia, and he expected his cut. A criminal who made a big name for himself and was not in league with Lotzia risked being run out of town if he was lucky. Respect for the way Kansas City operated made good sense.

If you were in good standing with Pendergast and Latsia, you had help when you ran into trouble. If you needed safe passage out of the state, Latsia had you covered. Was the heat in Detroit or Chicago too much? Latsia had a safe place for you. Kansas City was all about knowing the right people. When Charles Floyd arrived on the advice of his friend, he had no connections, no reputation, and no money. For now, he was a nobody.

But he wasn't ready for Kansas City. That would change soon enough, but at the moment, he made a nobody. in about face and headed home to Oklahoma. Charles was welcomed back by his mother and siblings and stayed briefly with his brother Bradley who had moved south to Seminole County and was working in the oil fields.

Again, it appeared that Charles might go straight. Bradley got him a job as a roused about in the fields. He hated the work, but he was happy to be near family, happy to know what the next day held. And while he heard the town gossip that Ruby might have been, have been remarried, he was happy to be back in Oklahoma where she was and hopeful to reconnect with his boy. But Charles' time in the seminal oil fields was short. Although he was getting along well with

management, it came to their attention that Charles had spent the better part of the last four years in a state prison for armed robbery. The drilling outfit had a strict no-felon's rule, and Charles was let go. The inability to get a second chance after serving, his time fueled Pretty Boy Floyd for the rest of his life. And it fueled his personal narrative as well. Like his hero Jesse James, he saw himself as a victim of a harsh world intent on making him a villain. He didn't necessarily want to go back to the life of crime, but he felt he was pushed into it. And with that, he returned to Kansas City. His new thought process was strengthened when he was arrested in early May for vagrancy. It was nothing more than local police harassment. Charles was a lot

of things, but he wasn't a vagrant. He had taken a room with a woman named Sadie Ash on Holmes Street, and that choice may have fueled law enforcement's interest in him. Ash's boarding house was known to be kind to the criminal element, the sort of place John Lotzia might stash a robber who was on the run. Additionally, Sadie's sons, William and Wallace, were dope peddlers who dabbled in prostitution. There was some talk that they were low-level members of one of the city's gangs, but there was also talk that they consistently snitched on their criminal counterparts to the police. The Ash Boys had met a pair of sisters, Bula and Rose Baird. William and Rose had already married and divorced, but Bula and Wallace were still married when Charles

arrived at the boarding house. One of the legends of Floyd's nickname was that Bula first called him Pretty Boy during a card game in the parlor. Whether she came up with Pretty Boy or not, Bula was attracted to the brash Oklahoma who carried himself with a sense of purpose and self-awareness that her current husband did not. While Charles had yet to establish himself in Kansas City, Bula felt he was destined for great things,

or at the very least, he was going to be a lot of fun. Charles fell for Bula as well, and it didn't take long for them to begin seeing each other. She quickly divorced Wallace Ash. In early May 1929, Charles and Bula traveled to Pueblo, Colorado, where Charles was quickly arrested for vagrancy again. He spent a week in jail before he and Bula headed back to Kansas City. While being brought in for questioning became a regular, occurrence for Charles in the early days in the city, he was able to avoid jail even though he was

making some money running moonshine. He had not, however, graduated to anything more grand as summer became fall in 1929. On Tuesday, October 29th, American financial luminaries, such as members of the Rockefeller family, began to buy large quantities of stock with the express purpose of restoring investors' faith in the stock market, but it was too late. The largest single-day sell-off in American history happened five days earlier on what became known as Black Thursday. The following Monday became Black Monday, and on Black Tuesday, the 29th, the American stock market crashed.

It had lost almost a quarter of its value in two days. The London Stock Exchange had crashed the previous month, and the 1920s immediately least stopped roaring. The Great Depression began, though the fall of the largest financial institutions in the country did not immediately affect the world of Charles Floyd. Despite prohibition, people were still going to drink. They were still going to gamble and dance. In fact, maybe they needed those things now more than ever. But two weeks after Black Tuesday, news came from Aiken's, Oklahoma that called Charles Floyd home. The Baird sisters went with him because there had been a shooting. When Walter Floyd had marched across the street and

confronted Jim Mills, the dispute started as angry shouting. Then it grew into threats of violence. Both men moved past the point of a simple business grievance. Now it was personal. Walter stormed out of his rival store, and even he wasn't sure of his intentions. In his own humble shop, his wife was waiting, and maybe she could calm him down. But also waiting was the gun he kept under the countertop. Maybe he was going for that, and Jim Mills didn't think he could take the chance. The streets were busier now. There were children playing, people bringing packages to the post,

and customers in both Floyd store and the Mills store. As Walter headed for his shop and maybe his gun, Mills followed a few seconds later. someone yelled for Mills to stop. Before Walter even heard Mills heavy footsteps in the dirt, he could sense the man coming up behind him. When Walter turned, Mills had a modified shotgun pointed straight at him. No further words were exchanged, and Mills fired a single round at close range.

The shot tore through Walter Floyd's body, doing irreparable harm. Walter crumbled to the ground, gasping and spitting blood. Jim Mills stood paralyzed in the street. It could have been the boom of the shotgun, or the sight of his rival, but also his neighbor, bleeding in the street and the sudden realization of what he had done. Mills just stood there. He didn't fire again, and he didn't run. He watched Walter Floyd stagger to his feet and lurch into his store.

Walter clutched his stomach where the shotgun load had torn a massive hole. He made it up the steps and into the. the shop. He slumped against the counter and died in front of his wife Mamie. When the sheriff arrived, Mills said he had acted in self-defense, even though Walter didn't have a gun. Mills claimed that the two men's tempers had gotten so hot that he was sure Walter was going for a gun of his own. Mills was taken into custody and charged, and now a jury would have to sort it out. In the days that followed, words spread to Floyd family members all over eastern Oklahoma, and it spread to Charles and Kansas City. The family gathered at the Aiken Cemetery to put their patriarch to rest.

Walter Floyd's epitaph read simply, Our Beloved One. He was just 51 years old. On the stand at trial, Jim Mills pleaded his case. He said that if he had not killed Walter Floyd, surely it would have been Jim's children and grandchildren gathering for a funeral. The jury bought it. It was self-defense, and Mills went free. Mills left Sequoia County not long after being found not guilty, and no one in Aiken's ever heard from him again. The rumors spread that Walter's son, the hardened criminal, had made quick work of Jim Mills on some back road. In Michael Wallace's biography of Charles Floyd, he relayed Charles' nephew's take on the tall tail, which went like this. Now, I'm not saying that Chalk or my father may not have wanted to kill Mills, because I think they

would have, but Chalk and my father never touched him. That's just the legends that came out, but there is not an ounce of truth to it. In reality, Charles had probably returned to Kansas City by the time Mills was last seen in Oklahoma. Whether legend or not, when the saga of Pretty Boy Floyd was written, the death of Jim Mills was pinned on Floyd. But at the present moment in 1929, Charles was on the verge of making the jump from small-time thief to full-fledged outlaw. And Charles Pretty Boy Floyd, maybe more than any other outlaw of the era, would suffer

from the blurred line between truth and legend. Next time on Infamous America, Pretty Boy Floyd's criminal career explodes. There are robberies, shootouts, daring escapes, mysterious murders, and more. 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 Valier. I'm your co-writer, host, and producer, Chris Wimmer. Find us at our website, blackbarrelmedia.com or on our social media channels. Or Black Barrel Media on Facebook and Instagram

and B-Barrell 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.