Now gather round me, children,
There’s a story I would tell
About Pretty Boy Floyd, an outlaw
Oklahoma knew him well.
– Woody Guthrie, “The Ballad of Pretty Boy Floyd”
Depression-era outlaws were partly produced by the mass unemployment, fury and despair of their times. There were enough of them to make a social phenomenon, not just an aberration. Often they came out of the poorest sections of the country. There was Dillinger, his sometime associate Baby Face Nelson, Ma Barker and her sons (‘the Bloody Barkers”) Clyde Barrow and Bonnie Parker, George “Machine Gun” Kelly — and Pretty Boy Floyd.
REH took an interest in them, as he did in other desperadoes. He wrote to H.P. Lovecraft:
At present Oklahoma is being ravaged by a thug called “Pretty-boy” Floyd, who seems to be a reversion to the old-time outlaw type. He has eleven men to his credit, seven or eight or which are officers of the law, which probably accounts for the failure of the authorities to apprehend him. It’s a lot easier to beat a confession of some sort out of some harmless poor devil than it is to nab a young desperado who wears a steel bullet-proof vest, and draws and shoots like lightning with either hand. (Letter of 24th May 1932.)
Whether or not REH was right about the rest, he seems to have been right on the money with his view of Floyd as a “reversion to the old-time outlaw type.” Charles Arthur Floyd was born on February 3rd, 1904, in Georgia. He came from a family of revival-meeting Baptists and grew up on hard work and the Bible, as one of (eventually) eight children. As a kid he was a good-humored joker, and like the other boys around, he reveled in the stories of the old-time outlaws like Jesse James, the Younger Brothers, and most of all, train and bank robber Henry Starr, a long-time outlaw whose record included a presidential pardon from rough-riding, trust-busting Theodore Roosevelt. Nobody guessed in his childhood just how thoroughly he’d follow in their footsteps.
His parents, Walter Lee and Minnie Floyd, were a farming couple who moved to Oklahoma when he was seven, to take up tenant farming in the green Cookson Hills, their crops corn and cotton. Walter Floyd was a bulldog for work, and he made his family one of the most prosperous in the area. He even had a car, which wasn’t common in Oklahoma before World War I. In 1915 he moved to the town of Akins, where the farming soil was more fertile, and continued to prosper. He managed to buy a truck and made good hauling freight locally. After that he opened a general store.
The Cookson Hills had been part of Choctaw Indian Territory in the old days, and the local brand of beer was called “Choctaw.” Young Charlie Floyd was fond of it, to the extent that he was soon wearing the nickname “Choc.” There was nothing vicious or violent about him as a kid; in fact, there seems to have been nothing about him that wasn’t completely normal.
He began turning towards the wild side when he travelled around picking crops with a work crew at the age of fifteen. Some of the other workers were roughneck vagabonds, hard drinkers, gamblers, skirt-chasers, some hiding from the law, and Charlie had to learn how to handle himself in a brawl to avoid getting bullied – something to which, easy-going or not, he was never willing to submit. REH would have fully agreed with him.
In 1922, Charlie and a mate broke into the Akins post office and made off with the colossal haul of a few dollars in dimes from the counter. Still, it was a post office, and that made it a federal rap, but they got away with it because the witnesses – local people who liked the lads – didn’t show in court. Charlie went to work on a farm after that, and then in an oil field, which may have turned him further away from his father’s honest example. Oil workers weren’t shrinking violets. REH’s letters hold various anecdotes about oil field bullies and head-breaking fights. One of his better known quotes is, “One thing about an oil boom – it’ll show a kid that life’s a pretty rotten thing faster than anything else I can think of.”
It probably wasn’t half as bad as the brute labor of picking cotton, which Charlie Floyd did after his stint in the oil fields. It was hell and he dreamed of a larger, wilder life. But he also met a girl named Ruby Hargraves, tall and dark with Cherokee blood, sixteen years old to his twenty, and married her in June of 1924. A son soon arrived, a boy “Choc” Floyd had wished to name after Jack Dempsey, but his wife demurred, and they compromised on “Dempsey” as the middle name. Like many other young married couples of the time, they found it rough making ends meet, and Charlie still dreamed of a wild life and plenty of easy cash. He encountered a nineteen-year-old two-gun thief named John Hilderbrand, who fancied himself both slick and impossible for women to resist, and promised “Choc” that as Hilderbrand’s partner in crime he could send his wife and son more money than he’d ever imagined.
Charlie went for it. They started small, robbing food stores and service stations, and then carried out their first really professional heist, an armored car payroll robbery that netted $11,500 to be split three ways. Unfortunately they were still green enough to buy a pricey new car and cruise the streets in it, tooting at girls, which attracted police attention. Charlie Floyd went down for five years, and the newspapers gave him the nickname “Pretty Boy” at that time – a moniker he always hated.
Woody Guthrie’s “Ballad of Pretty Boy Floyd” doesn’t mention that. It says he became an outlaw after going to Shawnee with his wife, and taking exception to some foul language used in her presence by a deputy sheriff. In the well-known words of the song, he grabbed a log chain, the deputy grabbed a gun, and the lawman got the worst of it, after which Pretty Boy had to make for the tall timber. That appears to be more romantic than the facts. Some later verses of the ballad, though they paint a glamorous picture of the outlaw, also describe his generosity to the poor. Pretty Boy WAS a multiple killer, and his victims did include lawmen, among them one patrolman cop and one Alcohol, Tobacco and Firearms agent. Still, he wasn’t as vicious as the Barkers, or Francis “Two Gun” Crowley, who was described as being willing to “kill at the drop of a hat,” and went to the electric chair at twenty. The Kansas City Massacre, the worst of the crimes Floyd was alleged to have committed, seems to have occurred when he was actually nowhere near.
He didn’t like prison any too well, and swore he’d never go there again. However, his wife divorced him while he was inside, and he may have felt he had nothing to lose after that. One of the few friends he made in the joint was bank robber Alfred “Red” Lovett, who told him bleakly that there was no going back now. “You’ll never find a decent job in a decent world. All you’ve got is your own kind.”
Charlie served his time without bitching or making trouble, got out, and headed for Kansas City with Lovett. Kansas City’s political machine was under the control of Thomas J. Prendergast, so crooked he made Pretty Boy and Lovett look like models of probity. Red Lovett introduced Pretty Boy around to the no-nonsense professional crooks of the town. Lovett was no tool of the machine’s, though; he liked his independence and didn’t trust the big boys of Kansas City. Pretty Boy followed his example, as his own nature inclined him to do, anyhow; he also didn’t care to be a puppet. But he liked the wide-open, nothing barred milieu of Kansas City. It had indeed, as the song said, “gone about as far as it could go.”
Being an ex-con, he was hassled by police and questioned over every holdup that took place. The questioning probably wasn’t gentle. This was 1929. Pretty Boy was discovering that Red Lovett hadn’t misled him about the slim chances of going back.
In November he returned to his home region of the Cookson Hills for a sad purpose; he had to attend his father Walter’s funeral. Walter Floyd had been killed by a fellow townsman, Jim Mills, in a petty dispute over the price of some lumber. Only days after Walter’s funeral, while Pretty Boy was still in town, Jim Mills disappeared without trace and was never seen again. Hiding a body in those boondocks would have presented no problem to a man who’d known the area from boyhood. Pretty Boy Floyd left for Kansas City again with no-one hindering him. But this writer feels morally sure he knew in exact detail what had befallen his father’s killer.
In Kansas City he joined the Jim Bradley gang. He’d known Bradley in prison and they got along. Bradley, Pretty Boy and seasoned bank robber Nathan King, with professional thief Nellie Maxwell (her specialty was shoplifting) went to Ohio and pulled a number of bank jobs there, but in Akron their luck ran out and they were captured. Bradley had shot down a police officer who tried to arrest him, and he drew the death sentence for murder. Floyd and King were given fifteen years each in the Ohio State Penitentiary. Pretty Boy, true to his oath that he’d never do time again, escaped from the train on his journey to prison, through the astoundingly simple ploy of asking to have his handcuffs removed while he went to the train toilet. He vamoosed out the window and was gone. “Astoundingly simple” would seem to have described his guards as well.
He made his way back to Kansas City to hide out. He knew it wouldn’t be a haven for very long. When he’d first arrived there, he’d stayed at a boarding house recommended by his friend Red Lovett. A former Sunday School teacher ran it, “Mother” Sadie Ash, but her Sunday School days were long over. Her two sons were small-time dope peddlers and bootleggers. Her establishment catered to criminals just out of jail, or keeping a low profile because the law was too interested in them for comfort. Pretty Boy had become the lover of Wallace Ash’s wife Beulah, nicknamed “Juanita”, who had divorced Wallace in the end, and now Charlie Floyd was back in town, they resumed their affair.
The Ash brothers were no friends of his. That didn’t worry Pretty Boy in the slightest. He became partners with a gunman named Miller, who had recently broken jail himself and was hotter than bubbling cheese, but Pretty Boy liked his nerve. Besides, and conveniently, the other Ash brother’s wife Rose (Juanita’s sister) had also left her husband, and taken up with Miller. The two robbers decided to get out of Kansas City forthwith and pull a series of jobs elsewhere.
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