Ruby gave birth to her baby on a cold winter’s day, December 29, 1924. A plump Monday’s child “fair of face” with cherry-pulp coloring, the baby had his father’s features and Ruby’s eyes. He was late for Christmas but just in time for the New Year.
Choc was right there when the baby came. He was delirious with joy. Some of Ruby’s kin, as well as a country doctor, were also in attendance. They cleaned up the baby, wrapped him up in a light blanket, and laid him in Ruby’s arms.
Relatives recalled that Choc kissed Ruby and gave her a wink. He picked up his son and held him tightly against his chest. Then he danced in circles around the room. Ruby got up on her elbows in the bed and smiled at the sight of her young husband and their newborn turning and swaying in the early sunlight. It was a sight she would remember for the rest of her life. Choc went to a mirror hanging on the wall over a chest of drawers and held up the newborn baby next to his face.
“Well, he looks just like me,” Choc told Ruby and the others in the room. “Just look at him!” It was a story Ruby would tell again and again until the day she died.
“Look at that,” Choc exclaimed as the baby balled his chubby hands into fists. “Will you look at this boy’s hands! He’s gonna be a fighter! A real fighter!”
Despite some mild protests from Ruby, there was no question in Choc’s mind what they would call their son. His first name was Charles, for his father and paternal grandfather, and his middle name was Dempsey, after the heroic prizefighter who Choc believed hung the moon.
Charles Dempsey Floyd: Any son named for his daddy and the world’s heavyweight champ had to be a contender. Most of the Floyds would call the boy Dempsey.
Ruby had decided that her baby would be delivered at the home of her aunt, Tempie Ring. The small house where Tempie and her family lived was located near Bald Hill, an oil field settlement seventeen miles northeast of Okmulgee, not too far from the Muskogee County line.
Ruby’s aunt had been born Tempie Laura Edwards on April 1, 1898, just one mile southeast of Sallisaw. She was the younger sister of Ruby’s mother, Sarah, who had died during childbirth. Ruby and Tempie became close and acted more like sisters than niece and aunt.
Tempie met her future husband, Jess Lee Ring, when he was working in the farm fields for her father, Perry Commodore Edwards. The young girl brought water and lunches out to the crews. They married on December 14, 1916, in Muskogee. Jess found work in the oil fields and they started their family. Jess Lee, Jr., was born in 1918; Ruth Josephine, 1920; and Frances, 1922. She did not know it at the time of Dempsey Floyd’s birth, but Tempie was pregnant herself. The following August, another daughter, named Eileen, was born. In sum, Tempie would have eight children. Betsy Lavona was born in 1928; Charles Dean, namesake of both Charley Floyd and ace Cardinal pitcher Dizzy Dean, was born in 1933; Shirley Anne in 1935; and finally, Barbara Jean in 1937.
Tempie’s children adored Ruby Floyd, and although they were actually her younger first cousins, they called her Aunt Ruby. That December morning when Dempsey was born, the little ones pressed around the new mother lying in bed and they peeked at her sleeping baby. Jess Ring kept Choc company, and every now and then, he pulled on a coat over his overalls and brought in more firewood from the stockpile out on the porch.
It was exactly one week after the solstice and the beginning of winter in the northern hemisphere. The new season wasted little time in making its presence felt. Just two days before the baby’s birth, the third in a series of cold waves raged southbound out of western Canada like a runaway freight train. The arctic blast slammed into the Rockies and sent fingers of icy air throughout the land.
In Oklahoma, snow covered much of the ground. The roads were slippery and the subzero temperatures caused a run on heating stoves and brought out a rash of warnings for police officers, railroad switch-men, and others who worked outdoors at night. Although there was a warming trend, Tulsans knew they would have to bundle up if they planned to attend the New Year’s Eve dances at The Winter Garden in the basement of the New Orpheum Theater or try the Louvre on North Main Street.
People throughout the state especially looked forward to New Year’s since Christmas had been soured by tragedy. At Babbs Switch, just a few miles south of Hobart, Oklahoma, a Christmas Eve fire started from a candle on a decorated cedar tree during a party in the schoolhouse. The building burned to the ground. Thirty-six adults and children perished. Most of them died from smoke and flames when they tried to flee the inferno in a stampede through doors that were quickly blocked with bodies. Heavy screens covered the windows and prevented escape. In the aftermath, only the basketball goals, a few outbuildings, and a barren playground remained. Five days later, as a new Floyd baby caused a celebration of life for a handful of people, hundreds of persons were still going to the site of the fire to remember all the deaths. Some stood and gazed at the jagged outline of the building. Souvenir hunters carried off bits of charred furniture, bolts, nails, and pieces of the screens. Ashes scattered in the wind.
It was snug inside the Ring house the morning of Charles Dempsey Floyd’s birth, however. A tamed fire burned brightly in the stove and there was plenty of wood. A big enamel pot of hot coffee never seemed empty. Tempie managed to rustle up some breakfast. Jess was not much of a drinking man, except for an occasional hot toddy, but Choc had a jar stashed in his grip and he laced their coffee with liberal slugs of woods whiskey. Outside, a layer of snow blanketed the fields. The cold spell seemed to snap as the temperature gradually climbed into double digits.
Choc picked up his sleeping son and teased Ruby that he was going to take their baby outside and roll him in the snow to see whether he was up to being a rough-and-tumble Floyd. When Ruby fussed and tried to throw a pillow at Choc, he laughed and returned Dempsey to her.
The weather across the state and much of the nation may have been harsh, but it was not bad enough to keep the lawless from their work. That morning, a fire believed to have been started by robbers destroyed nine buildings, including a Masonic temple and post office at Pottsboro, Texas, about eight miles west of Denison. The fire caused more than $150,000 in damages, and authorities found overturned and emptied safes in several of the burned structures. It was the identical modus operandi of bandits who had recently set fires and looted banks and business houses in the Texas towns of Valley View and Paradise.
The day after Dempsey’s birth, the news was again dominated by bank bandits. This time, four unmasked men looted the Farmers National Bank at Chandler, Oklahoma, of four thousand dollars in broad daylight, after the sheriff’s force was decoyed to the nearby town of Stroud on a false alarm. The holdup men were all described as being “less than thirty years old” and conducted the robbery in “a businesslike manner” with a minimum of talk. Three of them entered the bank and the fourth remained in the getaway auto with the engine running. Within hours, Governor Trapp had put up a three-hundred-dollar reward for their arrest and conviction. He also advised law officers to try to take the felons alive but if necessary to shoot to kill.
All the hubbub about banks and bandits did not get the attention of Choc and Ruby. Word of Choc becoming a father went over well in Sequoyah County. He proudly made the rounds at the homes of his relatives and friends. He wanted to show all of them that he was capable of producing more than winning poker hands and moonshine.
Choc and Ruby stayed with the Hardgraves at the time, and one day, after Choc had been off drinking, he came home and decided to take his baby son with him when he visited his parents. He managed to swing up on his horse with Dempsey cradled in his arms. He poked the horse in the side and started down the road. Ruby came flying from her folks’ house in hot pursuit. She grabbed Choc’s leg and begged him not to ride off in his condition with their baby. Choc only laughed and continued on with Ruby following him every step of the way just in case the baby slipped from his arms.
Mamie Floyd was near to the date when she would be delivering her own baby, so she remained close to the house. A little more than two weeks after Dempsey was born, she knew the time had come. When she went into labor, Mamie was just a couple of months short of her forty-fourth birthday. The baby arrived on January 16, 1925. Just as Walter hoped, it was another boy, to go with the three sons he already had and to balance out the four daughters. There were complications, though. The little boy was not strong enough to make it through the day.
They named him Chester Lee Floyd. They bathed and dressed him and laid him in a handmade coffin no larger than a grocery box. He looked like a sleeping angel. The family took him to the Akins cemetery, where in the wintertime fires had to be burned to thaw the ground for the grave diggers. The family later set a marker over the baby’s plot. Some words were cut into the stone. There was not much to say.
Chester Lee
January 16, 1925
“Budded on earth to bloom in heaven”
Mamie’s girls took care of things at the house and let their mother get some rest. Women from around Akins and the other small communities brought the Floyds pots of cooked supper, jars of preserved vegetables, and fruit pies. The preacher paid a call and told Mamie not to fret about her baby dying without being baptized. He promised that her little Chester Lee had gone straight to Jesus in the kingdom of heaven. Walter found his own kind of comfort. He closed his store and stayed drunk, but that lasted only a few days. A man had to eke out a living and go on with his business. Soon he was back at the store, telling lies with his friends and handing out sweets to his grandchildren.
Later that year, someone took a Kodak picture of Walter mounted on his horse with baby Dempsey sitting in front of him on the saddle. Surrounding the horse were Walter’s best hound dogs. Walter cherished the photograph and it became one of his prized possessions.
Besides showing off his son and sporting with his friends, Choc worked extra hard to support his family. In the spring, he and his father and older brother prepared their fields for a cotton crop, and when the new oak leaves got to be just about the size of a squirrel’s ear, he helped plant the seed corn.
However, Choc would not be around to harvest any of the crops. He would not be home for Christmas. Shortly after Ruby and Choc marked their first wedding anniversary, restlessness struck once again. He loved Ruby and Dempsey with all his heart, but he was dissatisfied with the meager wages he made from farming and peddling an occasional jar of whiskey. He packed up some clothes and told Ruby and his family that he was going out again on the harvest circuit, maybe back to Kansas or even Missouri, to earn some real money. He said that he hoped even to come up with a few luxuries for his wife and son.
Almost nine years later, Ruby—by that time gun-shy of the press and public—granted a rare interview. During the conversation with Kansas City reporter W. R. Draper, she shared some of the details of her life with Choc and discussed his decision to leave Akins in 1925.
“When we married at Sallisaw, Charley was a hardworking farmer,” Ruby told Draper. “But we never hardly saw any money, while the neighbor boys all seemed to have plenty. Charley took this for a while, then decided to do something about it. Charley said he had to make some money, so he left home without telling me where he was going. Some of the boys around Sallisaw said he was working in the harvest fields but I knew better, because he sent me money that he never could have earned so quickly.”
Ruby’s hunch about her young husband’s whereabouts was correct. Choc was up to no good.
Marvin Amos, the younger brother of Choc’s friend Cleon, remembered that Choc had paid a visit to the Amos home just before he departed. The Amos boys’ father, John Amos, was a man of many trades. Like most everyone else, he farmed and raised stock. He also did some barbering around the communities of Akins and Maples, owned a blacksmith shop for many years, and had served as a jailer under the sheriff. Old man Amos proudly claimed he was the first one in those parts to raise melons, and he was known as the Watermelon King.
It was also no secret that John Amos was one of the most successful bootleggers in Sequoyah County. Apparently, Choc had made up what he considered to be a smooth batch of moonshine, because he carried a jug of white lightning when he showed up to do some bartering.
“Choc came over to our place, and he traded five gallons of moonshine whiskey for a pistol my dad had,” recalled Marvin Amos. “It was a big ol’ pearl-handled pistol. I believe it was an ol’ forty-four. I just know it was big and heavy. Choc wanted it, so he gave my dad that whiskey to get it. That was right before Choc left this country. I recall he took the pistol and handed the whiskey over to my dad and said, ‘Here, you take this. I’m tired of tryin’ to make a livin’ with this stuff. Now I’m gonna give this here a try.’ Choc was talkin’ ’bout that gun when he said that.”
In late August of 1925, Choc Floyd left the beloved Cookson Hills behind. Besides a few clothes, he took with him photos of Ruby and Dempsey, and the pearl-handled pistol.
Right off, Choc hooked up with some bad company. His companion on the road was another young rapscallion named Fred Hildebrand. He was also known as the Sheik, the same moniker thousands of adoring movie fans had bestowed on Rudolph Valentino.
The two men had no money to speak of, so they hopped a freight train rolling out of Sallisaw and rode the steel rails into Missouri. Each passing mile brought them deeper into the land that was once home to Jesse James and a swarm of other salty bandits. Along the way, they met tramps who jungled up in makeshift camps near the tracks. Considered to be at the bottom of the working class, the men and boys kept their inconspicuous campsites neat and secure. Stealing from each other was the chief taboo in an unwritten code that governed these migrants as they made their way across the land.
The hoboes cooked batches of slumgullion and hotcakes they called “saddle blankets.” Mostly, they were honest men searching for work. They shared their vittles and strong coffee with Choc and his friend. Around the fire after supper, their hosts plied the young men with stories and explained the dangers of their nomadic life. Choc learned that to slip beneath a railroad car and “ride the rods” was tricky, but it was also dangerous to ride the blinds, the term used when a hobo stood astride the coupling equipment between the engine and first car. They were also warned to watch out for the railroad detectives, or “bulls,” who liked nothing better than to club a man senseless, pitch him from a moving train, or even bludgeon him to death with a length of railroad iron if they caught him hiding inside an empty boxcar.
The young men watched their step. They pushed on in a generally northeastern direction. Somehow along the line, Choc and Fred were able to come up with enough funds to finance their trip and allow Choc to send some money to Ruby in Oklahoma. As they moved across the Ozark highlands, they camped along the banks of the Meramec River, a stream lined with caverns and wooded bluffs.
Choc and Fred Hildebrand had no knowledge that early French and American traders had explored the same river and hiked through the clumps of sycamores and elms. They did not know that in 1774, a pioneer, ironically named John Hildebrand, had cleared a farm and built a cabin on the Meramec. They also did not know that some miles to the southeast in the lead-mining district, on a high bluff overlooking the Big River, was a cave named for Sam Hildebrand. Not a relative of either of the two other Hildebrands, this Civil War desperado used to hide in the cave after he bushwhacked his victims with a rifle he named “Kill-Devil.” Choc and Fred only knew that they were tired and hungry. In the evening, while they pulled beggar’s-lice from their clothes and washed off road dirt in the shallows of the cool water, cicadas sang in the treetops.
Ahead in a veil of coal smoke loomed St. Louis, spread along a crescent-shaped bend of the Mississippi River just ten miles downstream from its confluence with the Missouri. St. Louis was selected for settlement by French merchants in 1764 and was named for Louis IX of France. The fur-trading center eventually became the crossroads of Western expansion and outgrew its history by surviving hostile Indian attacks, cholera epidemics, the Civil War, and waterfront fires. It was said about this Midwestern metropolis that “the world passes through St. Louis.”
Famed for its shoe factories as well as its great breweries that were forced to come up with innovative alternatives after being stymied by the Volstead Act, the city had two major league baseball clubs, the second-oldest symphony in the country, excellent daily newspaper coverage, and a provocative past. St. Louis was also the largest city Choc Floyd had ever seen in his twenty-one years.
His visit there was brief but far from uneventful. It was also an experience he would never forget, for what Choc pulled in St. Louis was not just one more youthful caper. Making whiskey, running bootleg hooch, and breaking into a country post office to heist pennies were crimes bad enough. He had some scrapes with the law before, but Choc was about to enter a new realm. The good fortune he had been blessed with in the past was about to vanish.
After a few weeks in St. Louis, Choc headed for home. His sudden reappearance in Sequoyah County after being gone only about fourteen days immediately raised suspicions.
Choc and Fred showed up back in Sallisaw on September 13. It was a Sunday, and the church crowd was out in full force on the streets. The two young men who had left “bumming a freight” in late August came home in style. They had four-bit stogies in their mouths and were decked out in flashy suits and felt hats. They roared into town behind the wheel of a brand new Studebaker. They drove the shiny roadster down Cherokee Avenue past the shops closed for the Sabbath. One of the first persons to spot Choc was Deputy Sheriff Bert Cotton. He was well acquainted with all the Floyds, and had had a few encounters, mostly of a friendly nature, with them over the years.
Cotton was immediately dubious. He knew that when Choc Floyd put his mind to it, there was not a harder worker in the county. However, the law officer also realized there was not a harvest hand in the land who could earn enough wages in just two weeks to buy a new wardrobe and a fancy automobile. Cotton fetched Police Chief J. C. Woll and the two of them waved the Studebaker over to the side of the road, where they questioned Choc and Fred.
Their answers were less than satisfactory. For the most part, Choc was cooperative and neighborly but did little talking. Neither of the young men could reply when Cotton discovered two rolls of money, with one thousand dollars in each roll, hidden on Hildebrand. The money was still in yellow paper wrappers stamped with the name Tower Grove Bank of St. Louis. Within minutes, Choc Floyd and Fred Hildebrand were locked up in the jail house in Sallisaw.
In another of the cells sat Walter Daugherty, a sixteen-year-old who had been arrested the night before after he confessed to the stabbing death of Lonnie Whitney, his seventeen-year-old neighbor. The accused killer said that he and the victim had quarreled after a church meeting several days before, and they had agreed to a Saturday-afternoon duel to settle their differences. Knives were the weapons of choice. The boys walked ten paces apart, whirled about, and rushed at each other. Daugherty struck first and plunged his knife to the handle into Whitney’s heart. Death was instantaneous. When Daugherty was arrested, he was in the midst of taking care of his chores. Work had to go on. The recent blessing of more than two inches of welcome rain had broken the drought and benefited vegetable gardens. Some of the early cotton crop was already ripe enough to be picked.
It appeared there would be no cotton picking in store for Choc or Daugherty this season, however. By nightfall, word reached Charley’s kinfolk out at Akins that he was back home and in serious trouble.
“The day he was supposed to reach home I dressed in my best and got ready to go to Sallisaw to meet him because I supposed he would be riding in on the train,” Ruby Floyd later told W. R. Draper during her interview. “But before I could get ready and get started into town a neighbor came with bad news. He told me that Charley had been arrested the minute he struck Sallisaw because he was driving a brand new motorcar. Bert Cotton, the city marshal, just knew he could not have come by it honestly.”
Cotton was dead right. First thing Monday morning, he and Woll called the Tower Grove Bank to inquire about the two rolls of bills they had recovered with the bank’s name on them. They were then directed to contact the St. Louis Police Department, and soon the scenario of what had transpired in St. Louis unfolded.
On Friday, September 11, a trio of armed men in St. Louis had robbed couriers of an $11,929 payroll bound for the Kroger Grocery & Baking Company. The payroll taken in the holdup had originated from the Tower Grove Bank, and the bank’s name was on the yellow paper wrapped around the money. There were witnesses who thought they could identify the robbers. St. Louis authorities asked Cotton and Woll to keep both Floyd and Hildebrand under lock and key while they sent officers to Sallisaw to interrogate them.
An Associated Press story from Sallisaw on September 15 reported the arrests of Floyd and his friend in connection with the payroll robbery. A front-page headline in the Tulsa Tribune hit the nail squarely on the head: AUTO BETRAYS TWO BANDIT SUSPECTS.
In the column below the headline, Charley Floyd was described as “a police character.” There was mention of his involvement in the Akins post office theft. “Both men denied participation in the robbery at St. Louis,” the AP reported, “but have not been able to give a satisfactory explanation of their sudden prosperity, police officers said.”
Curiously, for several days that month, a book entitled The Rise and Fall of Jesse James, by Robertus Love, was being serialized in the Tulsa World. Love borrowed heavily from the writings of John Newman Edwards, the Kansas City editor who in the 1870s had romanticized James during the fabled Missouri bandit’s heyday. The excerpt published on September 11 was highly sympathetic to James. Not a few Cookson Hills readers thought at least one of the sentences about the old James outlaw applied to Choc Floyd’s situation as well: “We called him outlaw, and he was, but fate made him so.”
On September 16, 1925, Choc Floyd and his alleged accomplice—both charged with highway robbery—were returned to St. Louis for further questioning. It was indeed a sad day for the Floyd family. This time, there would be no way Walter could call in chits with Masonic brothers or make an alibi for his son.
“We came in from the country to Sallisaw that day they took him away,” remembered Bradley’s wife, Bessie. “There was Choc and they had him in chains. They had big ol’ chains on his hands and ankles. They had him chained to a pole at the train depot.”
Choc said so long to family and friends who were there to see him off. Despite the chains, he shook hands with his brothers and tried to make a joke. Nobody laughed. They could see the fear in Choc’s eyes. Everyone knew there would be a steep price to pay. He kissed Ruby and then he kissed nine-month-old Dempsey in her arms. According to Bessie Floyd, the baby made fists, just as he had the day he was born. For an instant, Choc smiled.
“I won’t ever forget seeing Choc standing there in those chains,” said Bessie Floyd. “Bradley just couldn’t bear to see his little brother all chained up like they had him. He had to turn away and I think he cried.”
The train arrived and the policemen with their prisoners boarded. At least this time, Choc would not have to jump a boxcar. He would ride inside in comfort and cover some of the same territory he had moved through only a few weeks before.
He was no longer free. Now he would not be eating in hobo jungles or sleeping next to streams. He would not be cooking up moonshine or playing poker under the stars or chopping cotton. He would not be hearing the call of hounds come autumn or sitting down to a country dinner on Sunday afternoons. He would not be making love to Ruby or playing with his son.
Choc Floyd was now a bandit.