Crime Library: Criminal Minds and Methods

CHARLES ARTHUR FLOYD: 'PRETTY BOY' FROM COOKSON HILLS

Reunited With Ruby

"I had a gal and her name was Lil
Down in the Arkansas.
I hugged that gal all over the hill
Way down in the Arkansas."

Down in the Arkansas

Choc wasn't one to depend on his reputation. To take some of the pressure off himself and Birdwell, Choc decided to lay low for a while. He had been missing Ruby and his boy Dempsey, and decided, in late 1931, to reacquaint himself with his family. Ruby had remarried in the meantime to a man in Coffeyville, Kansas, but when Choc traced her to her doorstep she immediately fell in love with him all over again. Leaving an apologetic note to her husband, Ruby dressed little Dempsey in his Sunday best and the reunited Floyds disappeared to Fort Smith, Arkansas, where they rented a home and adopted the alias of Mr. & Mrs. Charles Douglas. Birdwell followed with his wife and four children, chose his own pseudonym, and rented another home not far from the "Douglases".

It was a happy time, between September, 1931, and February, 1932. Dempsey was enrolled in a local school and life for the three Floyds became as normal as it could possibly be for a family of a gangster on the lam. Occasionally, Choc and Birdwell would "hit" one of the more remote banks in the area when funds ran low. Neighbors were told Choc was a traveling salesman from Kansas City, which would explain why he would disappear for stretches of time. On a bizarre note, their next-door neighbor was a deputy U.S. marshal.

"It was the best six months of my life, being with him," Dempsey later recalled in an episode of Biography aired in 1995. "He'd do a lot of funny things. He'd tease my mother, he'd cook for us, he'd make spaghetti and meatballs. He enjoyed cooking and doing things with us. He'd do the things a father does. At night, he'd pick me up and throw me on the bed. He had a lot of fun with me."

Of the relationship between his parents, he exclaimed, "My mother and father, when I saw them together, they were great, they were in love...He'd always have his arm around her. And it thrilled me to see them that way."

Choc loved horror films and would often take his boy to see the latest ones at the movie houses in Fort Smith. Dempsey vividly remembers the nights they saw Dracula with Bela Lugosi and Frankenstein with Boris Karloff. Of the latter, he states, "I was only six and it scared me. But (my father) kept holding me, telling me there was nothing to be scared of."

The happy
The happy "Douglas" family --
Choc, Dempsey & Ruby-- Ft.
Smith Arkansas, (Bettmann
Archive)

After several months, Ruby told Choc that she didn't like the schools in Fort Smith, and had heard from neighbors that Dempsey could get a better education in Tulsa. Obliging, Choc moved his family to a quiet area of that town, not far from one of Tulsa's nicer schools. After school, Choc would tumble and roughhouse with Dempsey and his friends in the back yard or play T-ball with them on a vacant lot at the end of the street.

But, trouble loomed. Residents on the block were whispering: about the odd hours "Mr. Douglas" kept; about the odd-looking fellow (Birdwell) who would pick him up in the dead of night, car lights off, engine idling, before the two of them vanished for days; about how the curtains were always shut; about how "Douglas" seemed friendly enough but turned his face away when others got too close; and, eventually, about how closely he resembled the picture on that wanted poster down at the court house, the one offering large rewards for "Pretty Boy" Floyd.

Choc could feel the unmasking. Once, when attending Sunday services at the Shawnee Baptist Church with Ruby and Dempsey, a member of the congregation drew him aside and asked point-blank, "Are you 'Pretty Boy'?" Choc hesitated, then answered, "Yes, I am. Next time you talk to the minister, give my regards and tell him I want to be saved."

Finally, it came. Acting on a tip from a neighbor, the police scouted the Douglas home in early February, 1932. They saw George Birdwell arrive at the front door and were convinced that the real resident of the house was the fugitive Floyd. Early morning, February 11, a detective named Frank Elliott ordered a hit. A squad of policemen surrounded the house while an armored vehicle rolled across its lawn. Officers chucked tear gas through the windows and waited. When no one emerged, they donned gas masks and broke into the front and back doors to find the house vacated. Choc, Birdwell, Ruby and a confused little Dempsey had fled through the yard only moments earlier; in the alley they split up, the mother and son heading on foot for the bus station, Choc and his partner back to the safety of Cookson Hills.

Ruby and her son were picked up that afternoon and her home turned topsy-turvy for clues to Choc's whereabouts. None were found. She insisted that she had not seen nor heard from Choc for months. But, when little Dempsey saw his father's file photo on the interrogator's desk at the station, he innocently replied, "That's my daddy! Him and Mr. Birdwell were at my house this morning!"

The little boy captured the authorities' hearts, playing and running through the squad rooms all night while his mother was sat questioned. Many who saw him, including reporters who flocked to the station, thought the child greatly resembled his father. Even the same "apple-blossom cheeks". By morning, with no reason to hold her, the police released Ruby.

All attempts to track down the elusive phantom having come to naught, Oklahoma politicians contacted recently retired sheriff of McIntosh County, Erv Kelley, who had a reputation as an intrepid hunter of badmen. They begged him to return to service just long enough to capture Floyd. A right-on-the-button and relentless pursuer, Kelley had brought to justice more bank robbers than any other sheriff in Oklahoma's history; he had a keen, Indian-like ability to pick up a trail where other lawmen were stumped.

Kelley accepted the challenge. The first thing he did was set up surveillance on the Floyd home where Ruby and Dempsey lived, figuring "Pretty Boy" would eventually appear there or they would go off to meet him. Helping Kelley maintain 'round the clock watch was a former deputy sheriff from Eufaula named, William Counts. On April 3, 1932, it appeared Kelley's hunch would manifest.

Rose and Dempsey left their home early that morning. The lawmen followed her to Bixby, where she parked her car at the Cecil Bennett farm, then walked with her son further down the road to a white two-story frame house owned by her father, Mr. Hargraves. The house was set back from the road behind a sturdy white fence with a gate. They saw the elderly Hargraves greet her and his grandson at the door and welcome them in with a smile. The scenario was ripe for a rendezvous between the lovers.

From Bixby, Kelley immediately telephoned for assistance. His hand-chosen crew consisted of Crockett Long of the Oklahoma Bureau of Criminal Identification, Sheriff Jim Stormont from Okmulgee, Tulsa detectives M.L. Lairmore and J.A. Smith, and a private detective from Oklahoma City, A.B. Cooper. Of course, Counts would remain on hand. As well, two farmers, crack shots, were recruited from the county and promised a part of the reward.

The posse gathered that night in town and headed out under cover of dark to the Hargraves farm. The Life and Death of Pretty Boy Floyd, by Jeffery S. King, describes the setup. "Four machine gunners were placed along the sides of the road leading to the gate, with Kelley and the two farmers forming a roadblock. Counts was 500 yards away at a schoolhouse, in the unlikely event the fugitives got through."

A little after two o'clock in the morning, the backup players concluded that Choc wouldn't show, at least not that night. There was not even the slightest hint of light inside the Hargrave house, indicating that no one was expected. The pre-dawn air blew chilly and they asked Kelley if they could hurry into town to bring back some coffee. "You boys go ahead never ya' mind me, I'll stay here just a bit more, just in case."

Fate. The others were gone no more than five minutes when Kelley heard the auto before he saw it. Peering into the cleft of darkness, he saw the turtleshell-shaped hood of a darkened vehicle creeping its way down the road in his direction; cautiously, it wheeled over the gravel at the gate to the Hargraves property. Kelley crouched behind the fence post where he had been standing. Cradling his machine gun, he watched.

The car parked several feet inside the gate and two men emerged. Neither of them spoke. From the twist of their silhouettes, Kelley could tell they were themselves studying the darkness around them that gangster instinct Kelley knew about so well. In a few moments, they would be up the stairs and inside the house. Now was the time to act.

"Throw up your hands, Floyd!" Kelley ordered, stepping from his cover.

He wasn't prepared for Choc's lightning reflexes. Choc's automatic had already begun to fire before the lawman completed his sentence. Even while Kelley's machine gun blazed back, the outlaw emptied his .45 into the dark form of Sheriff Kelley, hitting him seven times. It was only after the officer fell that Choc realized he had been hit, once in each leg and in the scrotum.

Birdwell, unhurt, had crawled back into the car and had was revving the motor. Choc grabbed the side of the open passenger door and collapsed into the seat. "Go!" he signaled Birdwell. Their tires spun, sprayed the area behind them with dirt, and the auto squealed from its place, skidded into the fence, backed up, and veered forward once more, this time into the night. William Counts, from down the property, had heard the bluster of Kelley's gun, but by the time he reached the open yard, Kelley was dead and his killers gone.

In life, Kelley had been a hero to many Oklahomans. His encounters with some of the toughest and meanest personalities had been legendary. Newspapers wept over his demise, the public wept louder. He had left behind a wife and children. "Pretty Boy" Floyd this time around did not emerge the hero of the fight.

"The Kelley killing...was the lone homicide on his rap sheet that (Choc) ever publicly discussed, although he always maintained that Kelley had been foolish to attempt an ambush...But, I think it bothered him," author Michael Wallis surmises. "He talked about it when he gave a few interviews to a few newspaper reporters. He was disgusted (with himself) because Kelley left behind a few kids."

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