Charles “Pretty Boy” Floyd — Robin Hood of the Cookson Hills

July 8, 2018

If violent, charismatic idol of the common folk Jesse James had a twentieth-century heir, surely it was Charles Arthur Floyd (1904-1934). This farm boy son of the Cookson Hills of eastern Oklahoma was weaned on the exploits of James and his fellow Confederate Guerillas. When the South surrendered, they did not halt their war against a Federal government who had ravaged their homeland. Floyd’s own legend loomed large enough while he lived that FBI Director J. Edgar Hoover named him America’s Public Enemy Number One. It grew larger still on the pages of John Steinbeck’s The Grapes of Wrath and when sung by Woody Guthrie as he strummed his guitar.


Floyd endures as one of the most fascinating and enigmatic figures in Oklahoma history. A lighting quick and deadly accurate marksman even when under fire, he committed spectacular felonies and killed lawmen. The final year of his life, American law enforcement from coast to coast threw its collective might, including numerous legendary individual lawmen, into the pursuit of this country boy criminal from Sequoyah County. Polite and good natured, however, he never shot first, did not commit most of the crimes attributed to him, and was so well liked from childhood onward by those who knew him and even many who did not, including numerous law enforcement officials, that the Cookson Hills became a virtual haven for him from the law.

The Cookson Hills of eastern Oklahoma, highlighted in green, where Charley Floyd grew up and often returned until the end of his life. Akins, the tiny rural community nearest his boyhood home, lies a few miles northeast of Sallisaw.

He despised his famous nickname of “Pretty Boy.” It reflected his striking, squared-jawed handsomeness, and was variously attributed to a girlfriend, a man describing him when reporting the first serious crime in which Floyd participated, and others. His family called him Charley, and they and friends called him “Choc,” apparently due to his appreciation for the well-known homebrew concoction credited to, at least with partial truth, the Choctaw Indians. (Southeastern Oklahoma-based Choc “beer” can be comprised of many ingredients, including barley, hops, sugar, yeast, rice, oats, mash, apples, peaches, raisins, fishberries, tobacco, and even a small amount of alcohol.)

Charley Floyd when first jailed at age 19 or 20.

The People’s Gangster

One reason for the conflicted views that have persisted regarding Floyd with many Oklahomans is the sense of Greek tragedy overarching even his entrée into crime. He possessed a gregarious, daredevil spirit like countless other energetic American boys who excel in athletics, which he did. Some Cookson Hills observers remembered him as the greatest basketball player ever produced by the area when he was in high school. Lawmen later remarked on his remarkably powerful and muscular physique, and, in their final pursuit of him, his blazing foot speed.

Charley with his Oklahoma childhood sweetheart and wife Ruby and her aunt Bessie Mayberry in Tulsa.

His daring led, however, through his own mistakes but also some bad breaks, to that life of crime. In particular, after completing his first prison term, he attempted to secure legitimate employment and “go straight.” Probably due both to his record and the onset of Great Depression economic calamity, he could not find work. He was also badgered by lawmen, including arrests for vagrancy, in various states. He eventually turned back to crime, and thus began the downward spiral that ended only with his death. Still, innumerable witnesses suggested that he was a very different sort of violent criminal.


William Cunningham’s acclaimed 1936 novel Pretty Boy helped lionize the image of this infamous desperado as some sort of Robin Hood character who robbed from the rich (bankers) and shared the proceeds with friends, family, and other poor folks. For a long time in the early 1930s, Muskogee reporter Vivian Brown dismissed such claims, numerous as they were. According to the Kansas City Star, however, Brown “traveled through the region and concluded that the tales were true: Floyd did give money to the poverty-racked farmers he befriended in those hardscrabble hills.” Brown herself eventually wrote in the Oklahoma City Times:


Like the famed marauder of the English forests, he took money from those who had it—the banks—and divided the proceeds with the poor. The penniless tenant farmers kept their mouths shut; they had no scruples about taking contraband wrested from bankers.


Mug shot of Floyd around 1930, the last time the law had him in custody until his death in 1934.

Eastern Oklahomans’ attitudes toward lawmen in a multitude of cases when they broached the subject of Floyd supports that notion. Shannon Magness of Sallisaw provided just one example:


The folks all around here knew Charley Floyd. And they liked him….My uncle, Taft Reed, told me that once when he was working on a local WPA road project, Charley pulled up in his car and handed the men on that job a bag full of money—just gave them all that bank money.


In The Life and Death of Pretty Boy Floyd, Floyd’s biographer Jeffery S. King chronicled the bank robber’s generosity in cash to those who helped him, such as letting him hide out in their home. According to King, Floyd provided groceries to a dozen poor families.

“It got to be common knowledge that Pretty Boy was around there, and had a good-lookin’ wife,” Thomas Pinson recalled of his early 1930s Tulsa boyhood. “But nobody was afraid or lived in terror or anything like that. In fact, he helped my dad change a flat tire down on the corner of Garrison Avenue one day. We all knew that Pretty Boy wasn’t such a bad guy. We always heard that he was good to most folks, and that he’d steal from the rich and give to the poor. He was no crazed killer.”


Floyd pulled over another time in the middle of the night to change the flat tire of a man who turned out to be a state legislator from Seminole. Deputies soon pulled over on the lonely road as he finished the task. When they lingered, Charley swung out his machine gun, disarmed them, and ordered them to “Get…out of here!” They did so, without harm, while Floyd skedaddled the opposite direction.

J. Edgar Hoover, the enigmatic genius most responsible for building the FBI. Catching “Pretty Boy” Floyd became a raging obsession for Hoover. He would eventually stop at little—if anything—to do so. 

Earlsboro native Pauline Alfrey recounted her and twin brother Buck’s experiences with Floyd:


We were just young teenagers trying to get through the Depression, and after school Buck and I would head for the old drugstore and each of us would get a nickel ice cream cone. One afternoon we were sitting there with our cones and in walks Pretty Boy Floyd. Everybody was buzzing about him. He was so handsome! His clothes were neat and he wore gloves. He ordered himself a Coca-Cola and drank it down, and as he turned to leave, he gave us a wink. Well, we were ready to leave, too, and when we went to pay for our ice cream, we found out he had already taken care of it for us. Were we ever happy! We had enough money to get a slice of pie!

The Floyd family—Charley, son Jack Dempsey, and wife Ruby—while living in Tulsa around 1932.

Legendary Gunfighter

Another factor helped forge Floyd’s legend. It garnered him interest, respect, and contempt, depending on one’s station in society. This was a singular series of daring, even sensational exploits. Hollywood epics then and now fabricated such deeds, but Choc Floyd actually did them. He lunged from a speeding, rolling, flaming car he was driving, then dragged his colleague to safety. He escaped from FBI custody in 1930 by leaping undetected off a moving train in the dark in rural Ohio while shackled. In 1931, a large posse of Kansas City detectives and federal agents sacked a bootlegging center. They captured everyone in the place except Floyd, who coolly feigned drunkenness at a card table, then pitched an object across the room to distract the cluster of lawmen, whipped out his .45, and bolted for the door. A ferocious gun battle erupted between Floyd and the laws. With nearly every officer in the building firing at him, he shot two of them in the card room, burst through a splintered door, and shot two more while racing down a hallway and stairs and out of the building, then speeding away.

The legion of false accusations against Charley Floyd—some of them historic crimes— far surpassed his actual number of offenses.

A scarcely believable series of shootouts and escapes on the streets of Tulsa in 1932 catapulted Floyd to near-mythical status in the national consciousness. On February 7, a carload of heavily armed detectives ambushed him and colleague George Birdwell at the intersection of Peoria and Apache. He emerged from his vehicle and raked the police car from stem to stern with machine gun bullets, wounding one lawman and sending the others scurrying. A running gun battle in speeding autos ensued in which one detective swore that he fired six shots at Floyd from point blank range without phasing him. Floyd and Birdwell escaped.


Three nights later, other lawmen ambushed Floyd and Birdwell at the intersection of Fifth and Utica. The bandits’ guns again roared back. Floyd shot out the police car’s illumined headlights and riddled its radiator, raced his own car up a steep hill and along the Frisco railroad tracks, then escaped on foot through the darkened area, through which he knew the pursuers could not follow him.

Ohio wife and mother Ellen Conkle and the dishes with which she fed Floyd his last meal. When she politely refused payment, he surreptitiously placed a $1.00 bill—worth around twenty dollars in 2018 currency—under his plate.

The next day, at least twenty officers, armed to the teeth and accompanied by an armored car, surrounded Floyd, and Birdwell, at his house. They fired tear gas into it. After no one emerged, they stormed the structure and found it empty. The robbers had blithely slipped through a cordon of officers in the back yard by using two rows of laundry hung on clotheslines as a shield from detection. The Tulsa World newspaper called it a “cool and daring” escape.


At this point, one of Oklahoma’s most respected lawmen, forty-six-year-old retired McIntosh County Sheriff Erv Kelley, volunteered his services to the state authorities to catch Floyd—and the enormous bounty now on his head. Kelley had hunted down and brought in fourteen bank robbers and six murderers in his career, without ever having to fire a shot. After three months of birddogging him, he succeeded in tracking down Floyd as well. Kelley and another man surprised the outlaw in the middle of the night when he attempted to visit his ex-wife Ruby and son Dempsey of Bixby. Perhaps the most famous gunfight in Oklahoma history ensued.


Though bushwhacked, the wary Floyd was alert and wary when Kelley drew down on him with a machine gun from eight feet away. Choc swung his Colt .45 up and blazed away in the face of furious and deadly fire. He was hit four times by Kelley’s machine gun, though all below the waist. Floyd’s aim was deadly. He hit Kelley five times in seven shots, two of them kill shots. So determined were these brave men that Kelley fell to the ground and died still pressing the trigger with his finger and spraying bullets into the dirt. Birdwell and a bleeding Floyd again outraced a phalanx of pursuers to safety. Soon, five hundred lawmen blanketed eastern Oklahoma in search of them. Sometime during this period, world-renowned Oklahoma aviator Wiley Post led a two-airplane search patrol.


In view of all these, and many other adventures, coupled with the general sense that he was at least partly “driven to it” by circumstances and an unforgiving system, as well as his congenial attitude and “never shoot first” ethos, it is not surprising that Floyd was roundly considered a latter-day outlaw in the romantic vein of Jesse James. Nor that Thomas J. Higgins, Kansas City Chief of Detectives, remarked that Floyd “had one of the quickest draws I’ve ever seen, and he’s the best shot with a pistol I’ve ever seen.”

Famed FBI Special Agent Melvin Purvis, who helmed the killings of America’s two greatest Depression Era outlaws, John Dillinger and Charles “Pretty Boy” Floyd. A jealous J. Edgar Hoover would soon railroad him out of the Bureau. Purvis committed suicide a quarter-century after Floyd’s death. Several famous actors, including Christian Bale and Oklahomans Ben Johnson and Dale Robertson, have portrayed Purvis in motion pictures.

A Bank Robbery Like No Other

Floyd’s most audacious exploit may have been robbing the bank at Sallisaw, around where he grew up. Best-selling author Michael Wallis set the stage in his seminal Floyd biography, Pretty Boy:


It was not as if (the job) was a well-guarded secret. Several of Choc’s friends, and practically the entire Floyd clan, including various in-laws and cousins, knew it was going to take place….Choc’s grandfather, Charles Murphy Floyd, who had just turned seventy-five the past September, got duded up in fresh overalls. He came into town from Akins that morning just to watch the proceedings. The old man took up a place of honor near the train station, directly across the street from the bank. Several of his cronies also gathered there. While they waited for Charley and his two friends to arrive, the men chewed tobacco and talked drought, the Depression, and politics.


From the moment Floyd got to Sallisaw till he left a half hour or so later, he chatted with friends and acquaintances. Casually toting his submachine gun in the crook of his arm, almost as though it were a formality, he cordially asked the barber next door to lay off his phone while he robbed the bank. “You bet we will,” the barber replied. “Good to see you fellas,” Floyd said, touching his cap.


“Howdy, what you doin’ in town, Choc?” a farmer in the street greeted him. “How you, Newt? We’re gonna rob the bank!” Floyd replied. “Give ‘em hell!” Newt responded.

The 1934 East Liverpool, Ohio Police Department, whose men played a crucial role in bringing down Charley Floyd.

In Wallis’s classic account of the robbery, as customers entered the bank, Floyd “greeted each of them with a big smile and shook their hands.” He called one friend out of the “captives” line and engaged him in a friendly conversation.


Sheriff Bert Cotton was an intrepid lawman who knew Floyd and had arrested him in Sallisaw years before for the crime that first sent him to prison. He sat in his police car around the corner, just seventy-five feet from the front door of the bank. He stated that he knew nothing of the robbery until friends informed him of it after Floyd left town.


“It was like the hometown performance of a great actor who has made good on Broadway,” wrote one newspaper reporter.


“Once again, Pretty Boy had taken the public’s mind off farm foreclosures and bank failures,” said Wallis of the handsome, athletic, winsome “Phantom of the Ozarks.” “His life was a continuous gangster movie for the disenfranchised to relish. The little people of the land fed vicariously from his exploits. Through Floyd, they were able to punch back.”


“I never shot at a fellow in my life unless I was forced into it by some trap and then it was that or else,” he told reporter Vivian Brown in her exclusive interview. The common folks knew it, and that it was different from other gangsters of the era.

A lawman holds the Colt pistols Floyd was carrying when he was shot down.

The Kansas City Massacre

During Floyd’s life and since, he has caught blame for far more deeds than the many he actually committed. These included a supposed “Supergang” robbery of a South Bend, Indiana bank with John Dillinger