“If you’ll gather round me, children,
A story I will tell
‘Bout Pretty Boy Floyd, an outlaw,
Oklahoma knew him well.
…
Yes, he took to the trees and timber
To live a life of shame;
Every crime in Oklahoma
Was added to his name.
But many a starvin’ farmer
The same old story told
How the outlaw paid their mortgage
And saved their little homes.
Others tell you ’bout a stranger
That come to beg a meal,
Underneath his napkin
Left a thousand-dollar bill.”
Those words come from “The Ballad of Pretty Boy Floyd,” a song by American folk icon Woody Guthrie. And it perfectly encapsulates the complex and controversial legacy left behind by one of America’s most notorious outlaws. Pretty Boy Floyd was a robber and a killer, no doubt about that. He became the country’s new “Public Enemy #1” after the death of John Dillinger.
And yet, many people remember him as the so-called “Robin Hood of the Cookson Hills” for his generosity towards the needy and, most famously, for allegedly burning mortgage documents whenever he robbed a bank to get people out of debt. But was this reputation deserved or did Floyd simply benefit from good post-mortem PR?
Early Years
Charles Arthur Floyd was born on February 3, 1904, in Adairsville, Bartow County, Georgia, the fourth of eight children of Walter Lee Floyd and Mamie Helene Echols. His father first worked as a railroad fireman, then as a miner, until he found his calling as a farmer. In 1911, the family packed up their bags and moved to Hanson, Oklahoma where they grew crops on a little plot of land.
The Floyds lived on the southern edge of the Cookson Hills, a large area covered in thick underbrush, with few, poorly maintained roads to get around. It had the reputation of being a favored hiding spot for people in trouble with the law and many an outlaw found refuge in the Cookson Hills.
Growing up, young Charles heard the stories of infamous ne’er-do-wells such as Bill Doolin, Belle Starr, and the Dalton Gang, who all passed through the Cookson Hills at one point or another, although he became particularly fascinated with the exploits of a Kansas criminal named Eddie Adams, who wound up in those parts after executing an escape while being taken to prison by train.
After a few years in Hanson, the family moved to a bigger farm near Akins, where the Floyds grew their own food and raised their own livestock. They also made their own cornmeal, lard, soap, and other items using food by-products, and soon enough, Walter opened a general store in Akins to sell their extra goods.
Overall, Charley, as his family called him, had a pretty happy childhood. And he was described as being a friendly, outgoing boy, fun to be around, who loved and respected both his parents and was protective of his siblings. There were just two issues with him. One – he wasn’t exactly valedictorian material. Once he knew how to read, write, and do some basic arithmetic, he said “That’s enough for me” and left school after sixth grade. The other was that Floyd also really hated hard work. He did it because he was told, but he never saw it as his future.
Charley began drifting down the dark path as a teenager. He started getting into fights and committing minor thefts. He even risked some jail time in 1923 when the 18-year-old Floyd was arrested for his role in a post office burglary, but lack of evidence and testimony from his father kept him out of the slammer…for now.
When he wasn’t getting into scrapes or trouble with the law, Charley was only interested in one thing – girls – and they were interested in him. He wasn’t called “Pretty Boy” for nothing, after all. Charles Floyd was a strong and handsome young man who liked to be well-dressed and well-groomed. Some say this is how he gained his famous nickname from people in the neighborhood, but there are several origin stories for the “Pretty Boy” moniker, so we’re not sure exactly where it started. We just know one thing – Floyd hated it, but it stuck.
He was hardly the only criminal who didn’t like his nickname, by the way. George Nelson hated being called “Baby Face,” and if you dared to call Ben Siegel “Bugsy” to his face, you risked catching a beating, even a bullet. These are all shameless plugs, by the way. We already did bios on those gangsters, if you’re interested. Finish watching this one first, but after that, if you still have a hankering for true crime, they’re all sitting there waiting.
Back to Floyd, he had another nickname since the time he was a teenager – Choc – due to his fondness for Choctaw Beer. He probably would have preferred everyone call him Choc Floyd, but it didn’t have the same ring to it. Anyway, in 1924, the 20-year-old Floyd married a 16-year-old farm girl named Ruby Hargraves, described as having “dark eyes, auburn hair, and a pretty face.” They had a son named Charles Dempsey Floyd. The three of them lived in a log cabin not far from the family home in Akins and Charley decided to give the whole “farming” thing a go. But this was not up his alley, so in 1925, Pretty Boy Floyd set off to look for alternative sources of income.
Start of the Spree
During that year’s harvest, Floyd met Fred Hilderbrand, a two-gun-toting hoodlum who, unlike Pretty Boy, got to pick his own nickname, so he went by “the Sheik” because he looked like Rudolph Valentino. Or, at least, he thought he did and who was going to argue? Hilderbrand was laying low after robbing an electrical manufacturing company of over $1,800. He told Floyd of all the easy targets the two of them could hit together and convinced him to tag along. In August 1925, Floyd got himself a revolver, kissed his family goodbye, and traveled with “the Sheik” down to St. Louis.
That month alone, the criminal duo robbed multiple grocery stores and gas stations. In September, their ambitions grew and they robbed the payroll being delivered to a Kroger Food Stores headquarters. Afterward, while talking to the press, the paymaster described Floyd as “a pretty boy with apple cheeks,” and this is another origin story of how Pretty Boy Floyd got his name.
The robbery might have been a success, but Floyd and Hilderbrand started spending money like there was no tomorrow. This made the police suspicious and when the authorities picked them up for a quick chat, they found thousands of dollars in cash on them, as well as money wrappers with the bank stamp on them. Floyd pled guilty eventually and was given five years at the Missouri State Penitentiary. His wife only found out about his extracurricular activities when she read about his arrest in the paper, and she divorced him while he was serving his sentence.
Floyd was paroled after three and a half years, but he had no intention of going straight. Quite the opposite, in fact. He made a few connections on the inside so when he got out, he made a beeline for Kansas City, Missouri, but before Floyd could do any serious damage, he received heartbreaking news from back home – his father had been killed by a neighbor named Jim Mills during a fight over some lumber. Floyd returned to Cookson Hills for the funeral and the trial, but Mills was acquitted on the grounds of self-defense. Mills disappeared soon after that. His body has never been found, but everyone always assumed that Floyd killed him as revenge for his father’s death.
Whether or not we can ascribe this murder to Pretty Boy Floyd, we cannot say for certain, although he made it abundantly clear in the years that followed that he had no qualms about taking a life. Floyd only returned to Kansas City for a short while, but it was enough to attempt to assassinate a detective named Burt Haycock who had been causing too many headaches for his underworld associates. Haycock survived his encounter with the outlaw and, because the detective saw his face, Floyd thought it best to find greener pastures. He joined up with a prison buddy named James Bradley and headed to Ohio.
First, Bradley’s gang committed a series of robberies in and around Toledo. Then, they moved on to Akron where things went south quickly. While driving, Bradley accidentally crashed his car into an oncoming vehicle. As two policemen rushed to the scene, he panicked and opened fire, killing patrolman Harland Manes. After that, the Akron police department was out for blood and scoured the city until every member of the gang was captured. Bradley was sentenced to death for the murder, while Floyd and the others were given 12-to-15 years for the robberies.
It looked like it was back to the Hoosegow for Pretty Boy, but he escaped on the way to prison, emulating his childhood role model Eddie Adams. During the train ride, Floyd had smuggled a handcuff key under his tongue. He asked to go to the bathroom and, after uncuffing himself, he broke the window and jumped out of the train. Floyd had sworn he would rather die than go back to prison and, ultimately, he would get his wish.
Cold-Blooded Killer
On the run from the law, Floyd opted for familiar surroundings and returned to Kansas City where he reunited with a lover named Juanita Baird. He also teamed up with a ruthless outlaw named Billy “the Baby-Face Killer” Miller, a much more experienced criminal who already had 28 arrests and five murders to his name. Together, they planned a spree of robberies up and down the country, but before leaving Kansas City, there was one final matter to take care of. Miller had hooked up with Juanita’s sister, Rose after she had left her husband, William Ash, who was also a malevolent malefactor of the city’s criminal classes.
Allegedly, William and his brother, Wallace, ratted out Floyd and Miller to the police, trying to get them arrested or killed. Either one would have worked fine, but the outlaws managed to escape and they wanted revenge. One night, the Ash brothers were lured to a meeting by a phone call from a woman. Their car was found on fire by the side of the road a few hours later. Their bodies were in a ditch next to the road, both shot in the head. No prizes for guessing who did them in.
Afterward, the foursome of Floyd, Miller, Juanita, and Rose left town and intended to go on a rampage through Missouri, Oklahoma, Kentucky, and Ohio. However, this team-up was short-lived and ended after only two bank robberies. On April 16, 1931, the gang was in Bowling Green, Ohio. The men were at the barbershop while the women were doing some shopping, but someone recognized their faces and called the police.
Chief of Police Galliher and Patrolman Ralph Castner approached the men and a shootout ensued. One shot from Galliher ripped open Miller’s neck and the gunman was dead before he hit the ground. Juanita also caught a bullet, but she made a recovery. Rose was captured and this only left Floyd. Confronted by Patrolman Castner, Pretty Boy emptied his gun into him, shooting him seven times before getting the hell out of Dodge all alone. Castner died a week later.
Following the murder, Floyd was as hot as a supernova. Even before this, he had gained a certain level of infamy, mainly because the papers loved writing about the “Pretty Boy” criminal who robbed banks and escaped from custody, but now he truly was one of the most notorious outlaws in the country. Floyd needed a place where he could lay low until the heat died down so it was back to Kansas City.
Pretty Boy hid out in a flower shop which was a front for a liquor business alongside another gangster named John Calio who was also wanted for murder. On July 20, 1931, police and Prohibition agents raided the flower shop. Special Agent Curtis Burks had the misfortune of running into Floyd in the backroom of the place. Floyd killed Burks without hesitation, then shot another three law enforcement agents as he was making his getaway, but they survived their injuries. An innocent bystander was hit and killed during the shootout and, lastly, when Calio refused to surrender and went for his gun, a policeman basically disintegrated his head with a point-blank shotgun blast. So yeah, overall a very bloody affair, which ended with Floyd, once again, free and on the run. With Kansas City in the rearview, Pretty Boy headed home to the Cookson Hills.
Robin Hood of the Cookson Hills
Floyd felt safe in the familiar environment of the Cookson Hills, but he had no intention of stopping his crime spree. If anything, he accelerated it. He teamed up with a childhood friend named George Birdwell, later adding a few more members to his crew and becoming an official gang leader. Together, they committed dozens of robberies in 1931 and 1932, although the exact number is difficult to pinpoint. As the song said at the beginning of the video, almost every robbery in and around Oklahoma started being attributed to Pretty Boy Floyd, including those he had nothing to do with.
The papers knew that Pretty Boy Floyd sold well, so rarely did a few days go by without a mention of the local criminal superstar. Sometimes, Floyd was accused of robbing two banks at the same time, in cities miles away from each other. Other times, he was even taunted about robbing specific banks, like the one in Inola, Oklahoma. One local newspaper wrote that Floyd wouldn’t dare rob that place because all the criminals were captured or killed during the previous five attempts.
The rewards on Floyd’s head totaled $6,000, dead or alive, and there was even talk of the governor bringing in the National Guard to hunt him down. He was starting to attain mythical proportions in Oklahoma, with some yokels even spreading rumors that Floyd always escaped the law because he was immune to gunfire. He wasn’t, as you will soon find out.
This was also around the time that his Robin Hood persona began taking shape. The Great Depression hit Oklahoma hard. Many people struggled to feed their families and risked foreclosure on their homes. But then Pretty Boy Floyd rode in, like a hero, to save them. How did he do this? Well, supposedly, whenever he robbed a bank, he destroyed all the mortgage documents to protect people from foreclosure. Sounds quite noble, but the question is – did he actually do this?
The answer is a rather unsatisfying “we don’t think so.” Pretty much every solid source only describes this act of benevolence as a rumor or legend. Even the FBI reports that Floyd might have done this once or twice, but it was certainly not a usual part of his modus operandi.
It is probable that Floyd bought food for starving local families from time to time, or that he gave them money directly, but this was not a completely selfless act, either. It was more of a gesture of thanks for not turning him in to the authorities, especially since Floyd had a large bounty on his head and he knew such a reward could be awfully tempting to someone in dire straits.
Overall, he made a pretty poor Robin Hood, especially when you remember the whole “killing people” part. His next victim was special investigator Ervin A. Kelley, a former sheriff of McIntosh County who had been tasked with the capture of Oklahoma’s most notorious criminal.
Kelley had a stellar reputation, having captured 14 bank robbers and six murderers. During Floyd’s time back in the Cookson Hills, he had reunited with his ex-wife, Ruby, and his son. Kelley knew that they were the perfect bait. Keep after them long enough and, eventually, Floyd would show up.
And show up he did, on April 9, 1932. Kelley had prepared an ambush outside a farmhouse a few miles west of Bixby where he believed Floyd would meet with Ruby. The lawman had six veteran agents and two deputized farmers with him. But as the hours passed and Floyd was a no-show, people were starting to get cold and hungry. Kelley allowed his men to take a break around 3 a.m., staying behind with only the farmers. This was his first mistake, putting his trust in untrained civilians who hid in the dark when the shooting started.
Minutes later, a car showed up with Floyd inside. Submachine gun in hand, Kelley stepped in front of the vehicle and issued a warning. This was his second mistake, allowing Floyd time to surrender instead of immediately opening fire. Of course, Pretty Boy did not hesitate and immediately fired his gun, hitting Kelley four times. The lawman squeezed off some shots, too, but only hit Floyd in the legs. The car sped off as Kelley collapsed to the ground and died.
The Kansas City Massacre
The summer of 1932 was a quiet one for Floyd, as he laid low to let his gunshot injuries heal. But by October, he had already recruited a new gang and was ready to get back to what he did best – robbing banks. The close call he had with Kelley did not deter him one bit. In fact, he was so cocky he even gave an interview to a reporter from the Oklahoma News. The Literary Digest proclaimed him Oklahoma’s “Bandit King” in its December issue and he even started having impersonators – other robbers who claimed to be Pretty Boy Floyd during their heists.
In November 1932, Floyd’s partner George Birdwell was shot and killed during a robbery in Boley, Oklahoma. Oh, well… No time to mourn when there are banks to rob. Pretty Boy found himself a new partner – a short, balding Texan by the name of Adam Richetti, and together they spent the first half of 1933 up to their old tricks. Things, however, took a drastic and violent turn in June, when Floyd was involved in one of the most audacious shootouts in the country’s history.
It became known as the Kansas City Massacre. On June 16, 1933, escaped outlaw Frank Nash had been apprehended in Hot Springs, Arkansas. Three agents were taking him by train to Kansas City, Missouri, where a team of BOI agents (the precursors to the FBI) and police officers were waiting to transport Nash to Leavenworth Penitentiary. Some of Nash’s criminal buddies had other ideas, however, and planned to bust him loose.
On the morning of June 17, the train pulled into Union Railway Station. Four officers went to meet up with the three already guarding Nash. They were all armed with pistols and shotguns and, together, they escorted the prisoner to a parked Chevrolet. As the agents were getting into the car, they saw movement from a nearby green Plymouth. Three men quickly surrounded the Chevrolet and one of them shouted “Let ‘em have it!” At that point, all three opened fire with machine guns. After emptying their magazines into the car, one of them approached the vehicle and said “They’re all dead. Let’s get out of here.”
In reality, only five of the eight men were dead, the other three having survived the attack. Frank Nash was among the dead, by the way, since he was right in the middle of that whole ordeal…So…worst…rescue attempt…ever?
In fact, the way it all went down made people think that it was never meant to be a rescue in the first place, but a hit to silence Nash. According to the FBI, the three gunmen were Floyd, Richetti, and another guy named Vernon Miller. Miller was found dead a few months later, executed gangland style, which helped further the theory that someone was tying up loose ends regarding Nash’s assassination. Although to be fair, Miller was the kind of guy who had lots of people wanting him dead for varying reasons.
As to Floyd and Richetti, the FBI gathered solid evidence that they were the other two triggermen. Pretty Boy sent a postcard to the Kansas City PD denying any part in the massacre, even though he was already wanted for multiple murders and dozens of robberies. Why or how they got involved in this remains uncertain to this day.
End of the Road
For the first time in his career, the cockiness had left Pretty Boy Floyd. There was a nationwide manhunt for him and he felt the noose tightening around his neck. Floyd and Richetti met up with Juanita and Rose Baird, who had been released from prison, and the four of them traveled to Buffalo, New York, rented an apartment under assumed names, and kept a very low profile.
1934 was a big year for law enforcement. First, Bonnie and Clyde were gunned down in May. Then, in July, John Dillinger bit the big one and in November, Baby Face Nelson was also killed in a shootout. Between Dillinger and Nelson, though, it was Floyd’s time to go.
In October 1934, the foursome decided to return to Oklahoma. However, just a few hours into their trip, they crashed their car into a telephone poll outside Wellsville, Ohio. While Rose and Juanita went into town looking for a garage, local police chief J. Fultz and a couple of officers investigated reports of two men loitering in the forest outside of town. They ran into Richetti and Floyd and a gunfight ensued. There were a few minor injuries, but no deaths, and the cops managed to capture Richetti alive, setting him up for a date with the gas chamber a few years later.
Floyd managed to evade the authorities once again, but he was on foot and he knew that a search party would be right behind him. He made it to East Liverpool, Ohio, before the law caught up to him. Floyd tried to hide in the woods, but the officers opened fire with everything they had – shotguns, rifles, machine guns, and revolvers. Considering how many shots were fired, it was surprising that Floyd was only hit twice, but twice was enough. He only made it a few more yards before collapsing to the ground. He exchanged a few brief words with the officers, mostly yelling “F**k you!” at every one of them. Then he said “I am done. You got me twice.” His last words were “I’m going,” and then Pretty Boy Floyd was dead.
