Pretty Boy Floyd in Tulsa

by Michael Wallis


The following is an excerpt from Michael Wallis’ Pretty Boy: The Life and Times of Charles Arthur Floyd which comes out in paperback this June from W.W. Norton.  It is reprinted here with permission from the author.

During the first week of January 1932, about the time of the massacre near Springfield and while state agents and deputy sheriffs turned the countryside upside down looking for Pretty Boy and his confederates, Charley had calmly moved his wife and son out of Fort Smith and relocated in Tulsa.  He rented a frame bungalow with a front porch supported by two stone columns, a double-pitched roof, and a garage at 513 East Young Street in a pleasant residential neighborhood a few miles north of downtown.

The house was just a short distance off North Frankfort Avenue, and only three and a half blocks east of Cincinnati Avenue, one of the major streets that connected the neighborhood with the business district.  The surrounding brick and frame homes were well kept, and the streets were lined with sycamores, elms, and catalpa trees.  Most of the yards had rose trellises and beds of iris, buttercups, and sweet peas.  There was a small neighborhood market a half block away and it was fewer than six blocks to the John Burroughs Elementary School, a one-story brick building located on a spacious plot of ground between North Cincinnati and North Boston avenues.  Nearby loomed Reservoir Hill, a more exclusive residential area.

Charley rented the house on East Young using his Jack Hamilton alias.  Ironically, the last tenant, who had moved out just two days prior to the arrival of the Floyds from Arkansas, was a Tulsa police captain.  After they unpacked, Ruby enrolled Dempsey, by then seven years old, at John Burroughs under the name of Jackie Hamilton.  He quickly made new friends at the public school and was careful never to use his true name.  During recess, he played on the sprawling grounds where in early spring the carpets of white clover blossoms could be tied into necklaces that brightened the heart of any schoolboy’s mother.

Ruby frequented the small grocery store operated by Mr. and Mrs. J.J. Smith at 502 East Young Street.  She also used the Hamilton name, and other people who lived in the neighborhood during that time remembered her as being attractive and cordial but not very talkative.

“She [Ruby Floyd] was a real nice woman who was very lovely-looking,” said Mrs.Smith.  “But like many Indian women, she didn’t smile very much.  The little boy was just as sweet as he could be.  I never met Floyd myself, but he and my husband used to talk often when Floyd would drop by the store.  My husband said Floyd seemed to be a pretty nice fellow.  We actually didn’t see too much of Floyd, though.  It was usually his wife who came to the store.  She told us her husband worked in the oil fields and only came home on weekends.”

Often Ruby would stop by the grocery and borrow a little bit of money from the Smiths to get her through until payday, which actually meant when Choc robbed a bank.  When her husband returned home, the money was promptly repaid.

“Mrs. Hamilton always paid her bills on time, even if she did pay in slightly corroded silver and hardly ever used paper money,” said Mrs. Smith.  “The silver looked like it had been buried for a long time.  We thought maybe they’d found some old money that was buried.  We had no idea where they got the money.”

The family kept to themselves and did not bother any of their neighbors.  Albert Hardgraves, one of Ruby’s three stepbrothers, moved up from Bixby and stayed with the Hamiltons for a while, and also attended classes at John Burroughs.

Thomas Pinson, a native of Carthage, Missouri, whose family came to Tulsa in 1922 so his father could pursue the wholesale grocery business, recalled the Hardgraves youth and the younger boy, from their fleeting school days at John Burroughs.

“My family had lived at 538 East Xyler since 1931, not far from where the Floyds had their rented house,” said Pinson when he was a seventy-two-year-old retired podiatrist living in Miami, Oklahoma.  “The Hardgraves boy wasn’t there with them very long, but when he was, he talked to some of us at school about his sister and brother-in-law, and we all knew that he was talking about Pretty Boy Floyd.  It got to be common knowledge that Pretty Boy was around there, and had a good-lookin’ wife.

“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.”

While some folks, such as people at the local grocery, believed Jack Hamilton worked in the oil business, others knew him as some sort of vendor.  One of Charley’s best tricks was to act as if he was a traveling salesman and pile lots of grips and bags in the back end of his car.  Then he would drive about as he pleased, posing as a drummer.

When he was home for a few days in Tulsa, he would take his family downtown to window-shop.  Once, while the Floyd’s car was pausing at an intersection, Dempsey recalled that his father saw a policeman standing on the corner looking at him.  Charley tipped his hat, smiled, and wished the officer well.  The cop returned the courtesy and Charley was on his way.  It was all a picture of civility.

During the brief period he lived in Tulsa, Charley often took the North Cincinnati bus downtown with Ruby and Dempsey to see a movie or go shopping. “Choc, Jackie, and I used to go to town every day,” admitted Ruby Floyd a few years after her Tulsa experience.  “We often rode on the bus.  No officer ever recognized him.”

On one occasion, the three of them went to one of the larger movie theaters to see Dracula, the horror film made in 1931 that starred Bella Lugosi as the bloodthirsty Transylvanian vampire.  Because of the nature of the picture, the management advised parents not to bring small children to the theater. The cashier in the ticket booth took a look at the couple and the small boy and advised Charley that this particular film would be too frightening for the youngster.  If Dempsey had handled Frankenstein, Charley knew his boy could take Dracula.  Ruby was uncomfortable.  There was a line of customers behind them.  She knew that after the long wait, Charley’s temper could reach the boiling point.  Charley glared at the cashier for a few seconds and the handed her the money to cover three tickets.

“Choc just shoved Jackie ahead of him and we went in,” said Ruby.


In Tulsa, even with the promise of spring around the corner, the working class was desperate.  By February of 1932, the central file of unemployed persons in the city contained almost twelve thousand names.  It was growing daily.  Charley was gainfully “employed” as the state’s premier bandit, but, like many of his fellow Tulsans, he also found February to be a stormy time.  If schoolboys had figured out that Pretty Boy Floyd had taken up residence in their neighborhood, then it was certain that the authorities would eventually make the same discovery.

Police officers began receiving the information that Floyd and Birdwell had been spotted in the city.  Detectives and uniformed officers relentlessly traversed the streets in the districts where Pretty Boy had last been seen.  Then during the second week of February 1932, right after Charley’s twenty-eighth birthday, all hell broke loose.

Late on the evening of February 7, several city policemen, acting on one of many tips, honed in on a suspicious sedan parked on a side street near North Peoria Avenue and Apache Street. Inside the automobile were two men whom the officers believed to be Floyd and Birdwell.  The unmarked police car approached the suspects’ vehicle at an angle, with the headlamps shining directly inside.  The cops leaped out with their guns drawn and called out for the two men to surrender.  Their answer was the bark of a tommy gun.

A fusillade of bullets splintered the police car’s windshield and tore apart the steering wheel.  In exchange of gunfire, Officer W.E. Wilson received a flesh wound from a submachine gun’s bullet.  The pair of men the officers were after sped away from the scene.  More than fifty rounds were exchanged, and one of the policemen later said that he fired at least six shots point-blank at the man he believed was Floyd.  The bullets had no apparent effect.  The entire police department went on a Pretty Boy Floyd-George Birdwell alert.

A few minutes after midnight on February 10, another running gun battle transpired between Tulsa police and two men, again identified as Pretty Boy and Birdwell.  As they made their way in an automobile near Fifth Street and Utica Avenue, the two men were spotted by Detectives Roy Moran and Homer Myers of the auto recovery squad.  The detectives opened fire with a sawed-off shotgun.  Much to the policemen’s chagrin, they were unable to continue spraying buckshot at the suspects’ car when they found out that the extra shells for their twelve-gauge shotgun were intended for a twenty-gauge weapon.  Once more, the two suspects were able to make their escape.


No matter which version was true, what is known is that about 5:00 a.m. on February 11 as many as twenty armed police officers led by Det. Sgt. Lon Elliot crept into the neighborhood and surrounded Charley’s rented house.  Fearful of Floyd and Birdwell’s shooting prowess, the raiders were supposedly armed to the teeth with shotguns and rifles.  They brought a plentiful supply of tear gas, as well as an armored transport truck.

Valuable time was lost, however.  The one and only machine gun owned by the police department was carried in Sgt. George Stewart’s scout cruiser.  Stewart only had two clips, each holding twelve shells.  That meant just two bursts of fire and the machine gun would be useless.  More than an hour was spent hunting additional ammo at the police station.  It was learned that the key for the department’s locked arsenal was with Milton L. Lairmore, the captain of the department’s pistol team.  A squad car hurried to Lairmore’s home.  He was awakened, and he handed over the key.  Then the squad car rushed back to the station, the ammunition was obtained, and the operation proceeded.

As the squad of armed detectives, trailed by the armored truck, came in sight of the house,  Ruby and her young son went out the front door, walked down the street, and disappeared into the neighborhood.  The officers spread out, with their guns aimed at the dark house.  Muffled orders were given and a tear-gas bomb crashed through one of the windows.  There was not a sound from inside.  Lon Elliot, who had concentrated most of his forces at the front of the residence, was puzzled by the lack of reaction.  A few minutes later, he understood why there was no response.  Bill Woods, an operative for the American Bankers’ Association, walked around to the street and informed Elliot that Floyd and Birdwell had already made a calm and cool exit out the back door.  Woods had spotted them as they escaped.

“Two men dressed in cark suits, wearing topcoats and gray hats, fled out the rear door just after the tear gas was fired into the house,” Woods told reporters.

Later it was revealed by a Tulsa Tribune composing-room foreman, who happened to live next door and witnessed the entire episode, that Floyd and Birdwell escaped by walking from the house between bed sheets hanging on a clothesline in the backyard.  Both men were armed but managed to slip away without a shot being fired.