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Gangster Charles Arthur “Pretty Boy” Floyd: Modern Day Robin Hood or Notorious Killer?

Eric Standridge is a freelance writer with an interest in history. His main focus is writing about Oklahoma.

The Roaring Twenties was a time of great celebration and independence, but in Oklahoma, it was also a time of bootleggers, outlaws, and gangsters. Charles “Pretty Boy” Floyd was the quintessential gangster, as he embraced both the independence and the lawlessness of the 1920s.

For nearly fifteen years, Pretty Boy Floyd was the bane of lawmen and a hero to the common man. Dubbed as the Robin Hood of Cookson Hills after the Great Depression, Floyd began to rob banks in order to help people instead of robbing banks for personal pleasure. The thrill of the hunt had left him, and now he had a more personal agenda, in his words, “If you ain't gonna do nothing to help the little guy, "Pretty Boy" Floyd will!”

From his humble beginnings, through the early days of his bumbling career, escalating into his days as champion to the common man, and finally, even in death, Charles “Pretty Boy” Floyd remains a legend and a hero.


Charles Arthur Floyd: An Honest and Hard Working Young Man

Charles Arthur Floyd was born on February 3, 1904 in Bartow County, Georgia to Walter Lee and Minnie Echols Floyd. He was the fourth child of eight, and quickly learned the value of hard work and family. Growing up, Floyd earned money by picking cotton in Georgia for nearby tenant farm workers, in addition to helping his large family work and maintain their own farm. Being standard during the early 1900’s, young boys were expected to join in the hard farm labor almost as soon as they could walk. Charles Floyd was no exception to this standard and did all that was required of an honest young man during this time.

In 1911, his family picked up their deep Southern roots and moved to the rolling Cookson Hills outside the small town of Hanson, Oklahoma. This move would prove to be the beginning of Arthur Floyd’s criminal career. At first, the family enjoyed a decent lifestyle working in the cotton fields of Oklahoma, but as their meager savings began to dwindle, their struggles began anew. Drought, plagues of insects, and devastating dust storms combined to keep them from gaining headway in the battle against poverty.

Oklahoma had always been a state opposed to the sale of alcohol, even before statehood. In 1907, when Oklahoma became the 46th, it was one of the first states to take part in Prohibition. Shortly before the 1920s hit, Arthur Floyd learned how to make corn liquor in order to supplement his family’s income. His life as a petty criminal began early, but it wouldn’t be until 1921 that Arthur Floyd would complete his first robbery.

Floyd married Lee “Bobbie” Hargrove at the age of 17, and they had a son soon after their marriage. Floyd always believed in family. In their poverty-stricken situation, he soon realized that he had to find a way to support his young wife and son. In 1921, he successfully completed his first robbery. By no means impressive, the $350 in coins that he stole from a U.S. Post Office provided what Floyd was looking for – a quick and easy way to earn what he needed in order to take care of his family. Beyond that, Floyd felt something during the robbery that he had never felt before; a sense of power.

Pretty Boy Floyd: The Birth of a Legend

Arthur Floyd got his true start in the business in 1923 when he met 19-year-old John Hilderbrand. Hilderbrand boasted of robbing a $1,900 dollar payroll, which infatuated Floyd. Over the next few months, Floyd learned the infamous art of the hold up. In 1924, he robbed a Kroger grocery store in St. Louis, Missouri and got away with $11,500 dollars in payroll cash. Exhilarated with the heist, Floyd went on a spending spree, purchasing expensive clothes and a new car. Police became suspicious of him, and Floyd was arrested just days later. He was sentenced to five years in prison, but was released after three. Those three years taught him a lot about how to perfect his art.

Upon his parole in March 1929, Arthur Floyd vowed that he would die before he ever returned to prison.

During the years in prison and soon after, a number of events happened in Floyd’s life that would change him forever. In his personal life, his young wife gave birth to a son, and soon after divorced him. After his parole, he went back home to Oklahoma and discovered that his father had been murdered by a local man. The man was tried for the crime but was acquitted. Soon after, the man disappeared. When Floyd first heard about the murder, he vowed that he would kill the man that murdered his father. Floyd was always suspected of killing him, but since there was no evidence, he was never charged.

Having lost everything that kept him tied to Oklahoma, Floyd soon moved to East Liverpool, Ohio. East Liverpool was known as a haven for bootleggers, liquor smugglers, and gangsters.  Floyd, seeing an opportunity, quickly began to hire himself out as an enforcer for many of the gangsters that operated in the area. It didn’t take long for him to earn a reputation as a cold, efficient killer.

Floyd’s travels brought him to Kansas City where he joined up with another criminal gang. Kansas City was another place where gangs ran wild, but many gangsters within the city were under the protection of the corrupt Pendergast political machine. It was with this gang that Floyd gained his two claims to fame: His skill with a machine gun, and the infamous nickname of “Pretty Boy.” Although Floyd hated the nickname, it caught on and soon elevated his notorious reputation.

A Modern Day Robin Hood

Pretty Boy Floyd’s image changed during the last five years of his life. He was always known as a local “Robin Hood”, but now that he gained national attention, he vaulted to the status of “hero” to the common man.

Since his parole in 1929, Floyd traveled throughout the middle states, from Oklahoma to Ohio. He robbed so many banks in Oklahoma alone that bank insurance rates doubled. Floyd is certain to have been involved in the infamous “Kansas City Massacre” of June 19, 1933, in which five men, including an FBI agent and several local police officers, were killed during an attempt to free a gang leader being transported to prison, although Floyd always denied being involved. Pretty Boy Floyd denied his involvement, and there may be some evidence towards that, but the evidence leading towards his involvement is still much greater.

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During his career, Pretty Boy Floyd killed at least 10 men, half of them lawmen, and robbed numerous banks, gas stations, and stores. Still, he was nearly worshiped by those who were less than wealthy. The lessons of hard work and dedication to family that were instilled in his youth remained strong throughout his life. During his bank robberies, he was known to have destroyed all of the mortgages he could find on the chance that they had not been recorded. This act endeared him to many of the local residents who were on the verge of losing their homes, farms, and businesses to the banks. After robbing the bank, he would casually toss money out of the window of his getaway car. At times, he would surprise people with his generosity. It wasn’t uncommon for him to hand out money as if it was candy. Floyd would return often to Cookson Hills, near present day Sallisaw, to visit his mother. While there, he would use some of the loot from his previous robberies to buy food and clothes for many of the poverty-stricken residents living nearby. If it hadn’t been for the Depression of the 1920s, Floyd probably would have taken up a reputable job and lived a long, law-abiding life.

The Death of a Legend

A long life was not in store for Charles Arthur “Pretty Boy” Floyd.

After gangster John Dillinger was shot to death in an FBI ambush in Chicago in 1934, Floyd was then named “Public Enemy #1”. A reward for $25,000 was posted for his capture, but other than lawmen, few were interested in the reward due to Floyd’s Robin Hood reputation.

In 1925, the governor at the time, M.E. Trapp, recommended the creation of an agency of special investigators to combat the outlaws. Shortly after, the legislature appropriated $78,000 to establish the State Bureau of Criminal Identification and Investigation. This agency was directly involved in the capture and execution of John Dillinger, and would eventually put an end to Pretty Boy Floyd as well.

The beginning of the end happened on October 19, 1934, when three men robbed the Tiltonsville Bank in Ohio. Two of the men were positively identified as Pretty Boy Floyd and Adam Richetti. Law enforcement had been closing in on the gangsters over the past two days, and now they had their precise location.

Floyd and Richetti were traveling with their two girlfriends on a wet, foggy evening of October 20th. Unable to see, Floyd crashed their car into a telephone pole. The two camped out nearby, neither wanting to leave the stolen money, as their girlfriends went to seek help. Sometime later that day, the two were spotted and reported to the local authorities.

Richetti was captured almost immediately, but Floyd managed to escape on foot. For two days, Floyd raced across the Ohio landscape, searching for a place to seek shelter. He ended up on the Conkle place, trying to hitch a ride, when the FBI finally caught up with him.

Floyd saw the officers and raced off towards a strand of trees, all the while ignoring the officers cries for him to stop. Just as he reached the tree line, gunfire rang out. Pretty Boy Floyd fell to the ground, and officers quickly raced to him. “I’m done for, you’ve hit me twice,” he said as the officers reached him.

The name “Pretty Boy” irritated Floyd right up to the moment he lay dying in an Ohio cornfield. When FBI agent Melvin Purvis stood over him and said, "You're Pretty Boy Floyd." The fading gangster flared, "I'm Charles Arthur Floyd." When asked about the Kansas City Massacre, he then said, I won’t tell you nothing.” With those words, Charles Arthur “Pretty Boy” Floyd breathed his last.

To say that Charles Arthur lived a good and decent life would be a lie. Instead, he did what he believed was right. The depression hit Oklahoma sooner than it did the rest of the country, and seeing the poverty around him, Charles Floyd did what he could to help. After he married, he no longer only had himself to look out for, but also a young wife and a newborn son. When desperation struck, Floyd didn’t see any other option than to do what he did.

As the depression worsened, Floyd began to strike back by creating a modern day Robin Hood. His fame is still well known in Oklahoma, as is his knack of escaping police traps. With his death, the era of the gangsters died with him.

The Kansas City Massacre

The Kansas City Massacre was the shootout and murder of four law enforcement officers and a criminal fugitive at the Union Station railroad depot in Kansas City, Missouri on the morning of June 17, 1933. It occurred as part of the attempt by a gang led by Vernon Miller to free Frank "Jelly" Nash, a federal prisoner. At the time, Nash was in the custody of several law enforcement officers who were returning him to the U.S. Penitentiary at Leavenworth, Kansas, from which he had escaped three years earlier.

The shootout ultimately led to the death of Charles "Pretty Boy" Floyd, who was identified by the FBI as one of the gunmen.

Pretty Boy Floyd Lyrics by Woody Guthrie

If you'll gather 'round me, children, A story I will tell 'Bout Pretty Boy Floyd, an outlaw, Oklahoma knew him well. It was in the town of Shawnee, A Saturday afternoon, His wife beside him in his wagon As into town they rode. There a deputy sheriff approached him In a manner rather rude, Vulgar words of anger, An' his wife she overheard. Pretty Boy grabbed a log chain, And the deputy grabbed his gun; In the fight that followed He laid that deputy down. Then he took to the trees and timber To live a life of shame; Every crime in Oklahoma Was added to his name. But a many a starving 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. It was in Oklahoma City, It was on a Christmas Day, There was a whole carload of groceries Come with a note to say: Well, you say that I'm an outlaw, You say that I'm a thief. Here's a Christmas dinner For the families on relief. Yes, as through this world I've wandered I've seen lots of funny men; Some will rob you with a six-gun, And some with a fountain pen. And as through your life you travel, Yes, as through your life you roam, You won't never see an outlaw Drive a family from their home.

Questions & Answers

Question: Did Charles Arthur "Pretty Boy" Floyd's wife work at a restaurant in Sand Springs, Oklahoma in the 1960's?

Answer: It is possible. Ruby G. "Bobbie" Hardgraves died in July of 1970 at the age of 63. She is buried in the Bixby cemetery, so she remained in the area up until her death.

© 2010 Eric Standridge


JOHNNT on January 13, 2020:

Where is the citation

Anna Schlegel from Novi Sad on May 13, 2012:

Oh, thank you! I read Bryan Burrough Public Enemies, but he does not answer the main question:Why I love Floyd? Have a great day!

60s on January 19, 2012:

this guy is a gangster legend and he represents the way gangs were supposed to help the community back when it first began

Austin on May 26, 2010:

It's nice reading about my 4th cousin

Tera Barrett, Black on May 14, 2010:

This is really neat to read, Pretty Boy Floyd is buried behind my grandpa and uncle in Akins Oklahoma. I knew the man that had the hancuffs that they put of him back in those days. I love reading this stuff.

Thank You for sharing...

Tera Barrett, Black

Pamela Oglesby from Sunny Florida on February 19, 2010:

Interesting story about Floyd, certainly things I didn't know. Good hub.

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