During those sultry days of July and August and on into September of 1931, Charley Floyd lay low. He kept his pistols oiled and loaded and at the ready at all times. He also continued to rob banks. Choc realized even then that as far as the law was concerned, he had gone beyond the point of no return. If he had wanted to call a halt to his bandit ways and settle down to a regular job, it would have been a tough challenge. He knew that he would have died just trying.
Even though a malevolent dark side had emerged in Charley’s personality, he could still be the sensitive country boy capable of demonstrating love and tenderness. He was never completely certain just whose bullets caused the deaths in the gunfights with police officers in Ohio and Kansas City, and he never really discussed with anyone the circumstances of the Ash brothers’ murder. He did own up to the biblical maxim that anyone who killed another man, killed a little bit of himself. In his late twenties, Choc told others he sometimes felt like an old man, always on guard and on the run, a man dying with each tick of the clock.
This was hardly surprising, since authorities in several states, including Ohio, Missouri, Kansas, Michigan, and Kentucky, were ready to tack the hide of the Pretty Boy, as many now commonly called him, to the barn door. Even if Charley had wanted to work at an honest job, which was not the case, the job market made this impossible. He had no education and had not touched the blister end of a hoe or shovel in years.
Choc had other skills, though. He was adept at swiping cars to use for bank job getaways. He could get an engine going and drive off while the owner ate dinner in a cafe or snored over a newspaper in his front room. Charley handled a revolver and a .45 pistol as well as anyone, and he learned to use a Thompson submachine gun with deadly accuracy.
His inclination was to stay on the scout and hope that his luck held. He kept in mind the old gambler’s saying that a faint heart never filled a flush.
Charley stayed mostly with Bradley and his family down at Earlsboro. Sometimes he slipped over to Sequoyah County to see his mother and kid brother, E.W., and his sisters and their families. He always paid his respects at the Akins graveyard. He also visited with his former in-laws, Jess and Maggie Hardgraves, and their three sons and daughter. The Hardgraves were living as sharecroppers in a small house that was not much more than a railroad car on the Cecil Bennett farm outside of Bixby, just south of Tulsa. They always liked Choc, even after Ruby divorced him and he became a full-fledged outlaw. Choc brought Maggie handfuls of wildflowers and praised her biscuits and gravy until she turned red. He persuaded the Hardgraves to tell him where Ruby and their son were living, and he finally got Jess to take him there.
They drove up to Coffeyville, just north of the Oklahoma line. A trade center of southeastern Kansas, on the west bank of the Verdigris River and bounded by a low range of hills, Coffeyville was the cattle and railroad town where the Dalton gang had been shot to pieces in 1892. The facades of some of the buildings on the downtown Plaza, at Ninth and Walnut streets, even in 1931 still bore the scars and bullets fired during the gun battle between the outlaws and citizens.
Jess took Charley directly to Ruby. When she opened the door and found her ex-husband standing there, she almost fainted. Charley Floyd was as unexpected as a fifth ace. Before her was the man she had committed herself to when she was a fresh farm girl. Now he was all dressed up in a suit and necktie. He smelled sweet. Ruby had kept up with his exploits through the newspapers and family friends. It was hard not to. She knew he was thought to be dangerous as lightning by the lawmen who dogged his tracks. But Ruby was not afraid of Choc. To her, he would always be Charley, and not the mad-dog killer the cops and headline writers wanted the public to believe.
As soon as they saw each other, Charley and Ruby realized they were still in love. Behind Ruby, in the shadows of the cramped apartment, stood Choc’s son—Charles Dempsey Floyd. The boy was six years old, and when Choc saw him, it was as though he were looking at himself in a mirror twenty years past. Charley broke out into a grin and swept the little boy up in his arms. The last time he had seen his son, Ruby had been holding Dempsey in her arms. They had been waving goodbye to Choc at the Sallisaw train depot as the St. Louis policemen took him off in chains to stand trial for highway robbery.
“That day when he and my grandpa came to our apartment in Coffeyville was the very first time I can ever remember really seeing my father,” recalled Dempsey Floyd. “That’s my first real memory of him. I liked him right off.” It was as if the three of them had never been apart. Ruby instantly forgave her wayward husband. She seemed to put aside the years she had spent waiting for him to show up again at her doorstep. Charley did not hold a grudge against Ruby, even though she had divorced him just weeks before he got out of prison. Dempsey took to his father immediately. In fact, he would not leave his side.
But there was a small hitch. Ruby had remarried.
Her new husband was Leroy Leonard, a twenty-two-year-old hardworking man she had met in Oklahoma. He was very much in love with Ruby, and he was kind to her little boy. Friends remembered that he treated Dempsey as if he were his own son. He had brought Ruby and Dempsey to Coffeyville, where Leonard worked long hours in a local bakery. They moved into a second-floor apartment over a store, and Leonard bought little Dempsey a tricycle to ride on the sidewalk out front. Every day around noon, Ruby packed a meal for her husband and gave it to her son to take to Leroy, who worked just a few blocks away.
“Leroy was always very good to me and my mother,” said Dempsey. “I’d bring him his lunch and he’d take a hot roll or bun and butter it all up and give it to me.”
That evening when Leroy Leonard came home from the bakery, he found that there was company at his apartment. Besides Ruby’s father, there was another guest. It was the man who Leonard had long dreaded would one day appear. Tension was thick in the little apartment, and the conversation soon became heated.
“Things got real bad when Leroy found out that my dad had come to Coffeyville to take my mother and me away with him,” said Dempsey. “They had quite an argument. It got real loud and there were some sharp words that were said that night. It didn’t come to blows but it still scared me to death. Finally my mother got them both to settle down.”
By nightfall, Ruby and Dempsey were packed. They left behind a saddened Leroy Leonard and drove south with Charley out of the town of Coffeyville.
Leonard’s heart was broken by the callous way Ruby treated him after he had been so kind to her and the little boy he loved. Although she had left him, he and Ruby remained married for a few years. Finally, in 1935, Leonard married a loving woman and they raised a family. Even then, however, problems sometimes arose because of people who became confused and believed his second wife, Bernice, had once been married to Pretty Boy Floyd.
There was always a strong rumor that Charley only wanted to throw a scare into Ruby by going to Coffeyville. A few said that he had even kidnapped Ruby and had stolen her and Dempsey away from the Kansas baker. That was not true; nor was it true that Choc was distrustful of Ruby, despite what some of his friends from Sequoyah County told nosy reporters.
“He never got over the fact that Ruby married another fellow while he was in the Missouri prison, although he did take her away from that fellow and live with her again,” one of Choc’s schoolmates told a Kansas City reporter two years after Charley and Ruby’s reconciliation. “But he never did have much confidence in her.”
Choc had enough trust in his former wife to take her and their son to a rented home he found in Fort Smith, the second-largest city in Arkansas. Although Choc continued to maintain a relationship with Juanita Beulah Baird, he also tried to pick up with Ruby where they had left off in 1925. They never remarried, but for periods of time, they lived together as if they were once more husband and wife.
Choc and Ruby’s home in Fort Smith—a city at the junction of the Arkansas and Poteau rivers where “Hanging Judge” Parker used to deliver his stern brand of frontier justice—was in a quiet residential neighborhood not far off Garrison Avenue, the main downtown artery. Sallisaw, where Choc’s widowed mother and several members of his family resided, and small communities such as Akins, Hanson, and Price’s Chapel were within easy driving distance.
Ruby and Charley, living under the alias of Mr. and Mrs. Jack Hamilton, and their little boy, were settled in their neat residence by the late summer of 1931 just in time for Dempsey to begin the first grade in the public school system. Fort Smith would be their home for almost six months. It was unquestionably the happiest period of their lives together.
“My dad stayed with us almost the entire time we lived in Fort Smith,” recalled Dempsey. “It was a wonderful time. My folks took me to the local school, but since my dad was using the name Jack Hamilton at the time and was acting as if he was a traveling salesman, they enrolled me as Jackie Hamilton. A lot of people always thought they called me Jack or Jackie because of my name Dempsey, but that really wasn’t the case. It was just to go along with my dad’s alias. The folks really drilled me about using that name, and they had me say it over and over again so I wouldn’t slip up and use the name Floyd in front of strangers. They got me accustomed to the name, and that’s what many people called me.”
To the Floyd side of the family, the little boy was still Dempsey whenever he came to Oklahoma for visits, but Ruby’s relatives and many of her friends always referred to him as Jack or Jackie even after he was a grown man.
“I really have nothing but fond memories of my father, especially when we were in Fort Smith,” said Dempsey. “He was a great father to me. He was gentle and he would make me and my mother laugh all the time. His sense of humor was terrific. He was always telling jokes and teasing my mother.”
One afternoon, soon after he started school, Dempsey came home and showed Charley some crayon pictures he had drawn. Choc told his boy how much he liked the artwork, and then he got a devilish look.
“He told me, ‘I want you to go out in the kitchen and tell your mother something.’ He whispered in my ear and sent me to her,” recalled Dempsey. “So I did as he told me. My mom was at the stove cooking supper and I said, ‘Mother, guess what I did at school today.’ Well, I guess she expected me to say that I made this picture or I learned this or that. She smiled and said, ‘What did you do today, son?’ And I repeated what my dad had told me to tell her. ‘Oh, I got into a little girl’s pants today,’ I answered—without even knowing what I was saying.
“Mom ran right into the front room and jumped on my dad. She pounded on him with a pillow and scolded him, and they wrestled around and laughed and laughed. Of course, I had no earthly idea what was going on. At that age I couldn’t imagine what I would be doing with some little girl’s pants.”
Charley and his son pulled other fast ones on Ruby.
Dempsey was walking home from school one rainy afternoon and got sidetracked by some little boys who were hauling each other up and down a tree in a bucket attached to a rope and pulley. It was great fun and Dempsey lost all track of time. When he came through the back door and was confronted by a worried Ruby, it was after dusk.
“My mother was in tears,” said Dempsey. “She was deathly afraid that someone had kidnapped me, so she marched in and told my father, ‘Charley, you are going to give this boy a whipping. You’ve never whipped him in his life but the time has come for you to do your duty.’
“My father looked up at her and said, ‘All right, Ruby,’ and he told me in a serious voice to go into the bathroom. I was standing there with my raincoat on, and he walked in with his belt in his hand and closed the door. Then he bent down and whispered, ‘You take that coat off and put it over the toilet stool. Every time I smack that coat, you holler and scream your head off like you’re really getting a good beating.’ So he started pounding away on that raincoat with his belt and I yelled bloody murder, and before too long, my mother was trying to break the door down to get him to stop. We never told her the truth.”
Charley spent a lot of time around the house at Fort Smith, getting reacquainted with Ruby and becoming a father to Dempsey. Both baking and cooking relaxed Charley, and he did his share. He donned one of Ruby’s aprons and especially enjoyed sliding a hot apple pie out of the oven. He hummed “When the Moon Comes Over the Mountain,” “Love Letters in the Sand,” or “Where the Blue of the Night Meets the Gold of the Day” as he prepared spicy Italian dishes he had sampled during his days in Kansas City and Akron. Spaghetti and meatballs were his specialty.
“Dad used to take me fishing, too,” said Dempsey. “This one day we were way out in the country at some lake, and we just couldn’t seem to catch anything. So after a while he turned to me and said, ‘You know what we ought to do? Let’s teach these damn fish a lesson and shoot ’em!’ I was thrilled! He went to the car and brought back his submachine gun and he sort of held it for me and let me fire it into the lake. Of course, we didn’t hit anything, but we had a good time. ‘That’ll show those fish,’ Dad told me. ‘If we can’t catch ’em, we’ll at least scare ’em to death.’”
Like other families who tried to keep their minds off the Depression, Choc also looked forward to taking the family to the movies. One of Charley’s favorites was the horror classic Frankenstein, which premiered in 1931. It was directed by James Whale and starred Colin Clive, Mae Clarke, and Boris Karloff in the title role. Karloff gave a strong, sensitive performance as the synthetic brute who discovers his own humanity yet is compelled to kill and terrorize. Dempsey scrunched down in his seat and hid his eyes when the monster came on the screen, but Charley sat spellbound for seventy-one minutes.
“I remember I was so scared of Frankenstein,” said Dempsey Floyd. “But my dad sat down with me and explained it was just a movie and that I shouldn’t be afraid.”
To all those who knew the young couple and their son, it was an idyllic period. Ruby went shopping in Fort Smith and drove up to Muskogee and Tulsa. She bought all of Charley’s sporty clothes, including silk underwear, neckties, fine socks and shoes, scarves, caps, and the black leather gloves he loved to wear. On sunny afternoons, they went outside in the yard and took family photographs and had picnic lunches. All the neighbors admired the Hamiltons. They seemed to be getting along “just swell” on a salesman’s commissions, in spite of the bleak times.
“My folks were so good-looking,” recalled Dempsey. “My dad was handsome and had that thick hair. He was well built and had such strong arms and shoulders. My mother was tall and beautiful. She was affectionate and loving.
“I used to get up out of my bed there at our place at Fort Smith real early in the morning when it was still dark and quiet, and I’d go to their bedroom and peek inside. I can still see them together asleep in their bed. My mother would be in his arms and their heads would be together like sweethearts do. Their faces were so young and innocent. They looked like sleeping kids. She adored my father and I believe she would have gone anywhere with him.”
Charley clearly would have taken Ruby anywhere he went except when he visited his other love interest, Juanita, or when he ventured forth to pull a bank robbery. He felt that being on the scout was no place for a woman. Robbing banks was a man’s job.
By the late summer of 1931, Charley had lined up yet another partner as a running mate. His name was George Birdwell and he indeed was all man.
Born in the Cherokee Nation in 1894, Birdwell had Irish, Cherokee, and Choctaw blood, and even as a kid he was prideful and stubborn as a pack mule. His father, James Joseph Birdwell, moved to Texas and farmed, while young George learned to cowboy. With his family, he moved back and forth between Texas and Oklahoma and received his first real notoriety in July 1913 when a farmer named T. W. Jennings, from the Mellette community not far from Eufaula, Oklahoma, shot Birdwell because he suspected the farm boy of fooling around with his wife.
The story was that Jennings’s wife had seduced young George, and the jealous husband had filed suit for divorce. In the petition, he named Birdwell as correspondent. When Jennings later encountered Birdwell working in a cornfield, the farmer yanked out a gun and opened fire, striking the young man in the leg, just above his knee. George managed to mount a team of plow horses and escape further damage. He rode to his brother Robert, who put a tourniquet on the wounded leg and then took George on horseback to a doctor thirty miles away. The ride was fast and furious and the horse that carried the two Birdwell boys dropped dead in its tracks. The doctor patched up the wound and George soon recovered. Jennings turned himself in that same evening at Eufaula, was placed under five-hundred-dollar bond, and was released. He was never punished for gunning down George, and the two men stayed clear of one another in the future.
Birdwell never lost his way with the ladies, and he developed a taste for strong drink, as well. He kept at least part of his wild streak even after he married. His wife, Flora Mae Birdwell, was born in the Cherokee Nation in 1898, and from the time she was a girl, she was called Bob by all those who knew her. Bob Birdwell worked hard to make a home and helped midwife her share of babies when she and George lived on a cattle ranch in Texas. She also had two boys and two girls of her own. The Birdwells also raised two of Bob’s nephews.
Their oldest son, Jack, was born on the Texas panhandle ranch where George served as the foreman. Located in Hall County, not far from the towns of Esteline and Parnell, the ranch was near the Prairie Dog Town Fork of the Red River. The largest town for miles around was Childress to the east.
George Birdwell was six feet tall. He weighed in at an even 150 pounds, and would not have been caught dead without his Stetson hat and high-heeled cowboy boots. His high cheekbones and dark complexion gave away his Indian heritage. He was lean, bowlegged, and could ride and rope as if he were born in a saddle. Through the years, Birdwell competed in many rodeos. He rode bucking broncs and roped goats four-legged at ranch roundups in West Texas and at rodeos in Shamrock, Drumright, and several other spots in Oklahoma. At a rodeo in Oklahoma City, he once roped a goat in the remarkable time of nine seconds flat.
Shortly after the birth of his first child, Birdwell quit ranching to work in the oil fields. He labored for an outfit outside of Shamrock, Texas, and later took his family to live in several small oil patch towns in Creek County and other boom areas in Oklahoma. Birdwell was an able roustabout and also worked at various refinery tasks. It was said that he could “dig a ditch like a gopher.” By the latter part of the decade, George found a job with Magnolia Oil and the Birdwells moved near Earlsboro, close to the home of Bradley Floyd.
Birdwell first met Bradley’s younger brother in 1929, right after Charley was released from the penitentiary in Missouri and returned to Oklahoma to find a job with Magnolia. The Floyd brothers and Birdwell became friends and the three of them made a little bit of money by bootlegging in the area.
“Charley Floyd came down there to work, and had hardly got started when the foreman came by and grabbed him off the job,” recalled Jack Birdwell. “My father said that the foreman told Charley, ‘I don’t want no thugs around here.’ That’s when Charley decided he was gonna show ’em.”
By early 1930, as the Depression reached the oil patch, George Birdwell was laid off from his job with Magnolia. He knew peddling whiskey and shuffling poker cards were not going to bring enough money to keep his wife, four kids, and two nephews in food and clothing. That was about the same time that Charley Floyd returned to the area and rented a house in Shawnee with the two Baird sisters and another young man named Bill Miller. Charley and Miller got together with Birdwell and Bradley and discussed some options.
“That’s when they went to robbin’ banks,” said Jack Birdwell. “Charley wouldn’t let his brother go with them. Bradley wanted to, but Charley told him no way. My dad was with Charley and Miller that first time they robbed the bank at Earlsboro. Dad was wearing his sheepskin coat and had his cowboy hat pulled down over his eyes and face. It was the first time he ever robbed a bank.”
That robbery of the Bank of Earlsboro took place on March 9, 1931, and the three bandits—Choc Floyd, Bill Miller, and George Birdwell—got a total of about three thousands dollars. The holdup at Earlsboro occurred just before Charley and Miller returned to Kansas City, only a couple of weeks prior to the slayings of the Ash brothers across the state line in Kansas. The money they took from Earlsboro provided them with an infusion of cash. It helped finance Choc and Miller when they left, accompanied by the Baird sisters, for Kentucky and Ohio, where Miller met his bloody end on the streets of Bowling Green. Birdwell, who had no intention of joining the four lovebirds on their odyssey, used his share of the take to help pay a pile of bills and keep a roof over his family’s head. He also came to the financial assistance of some down-and-out friends.
“Whenever he made a haul from a bank, Dad always helped out others,” said Jack Birdwell. “He’d give each of our neighbors a twenty-dollar bill. That went a long way back then.”
By late summer of 1931, however, Birdwell was in need of more money. He still had no job. He was ready to sally forth again with Choc Floyd and hit more rural Oklahoma banks.
“My father was a proud man, and he would not take help from anyone,” said Jack Birdwell. “He didn’t want any relief. I can still hear him when I was just a little kid sitting on his knee in an old Model T Ford working the gas for him and he’d tell me about what to expect from life. He said way back then that there were two kinds of people who robbed—some who did it with a gun and some with an ink pen. He told me to be my own person and not ever to have a price. ‘Don’t let anybody ever buy you,’ is what he told me.”
Beginning with the robbery of the Bank of Earlsboro in March of 1931, George Birdwell’s bandit career lasted only twenty-one months. During that period, he robbed thirteen banks with Pretty Boy Floyd. In most cases, they recruited one other person, usually one of several younger men they knew, to drive the getaway car. All of the robberies were in Oklahoma and none of them ever netted more than four thousand dollars. The average sum taken was usually a little more than half of that amount.
Accused of holding up more banks than they actually robbed, Choc and Birdwell, in fact, struck at six banks in Oklahoma during the five-month period between August and December 1931.
On August 4, they entered the Citizens Bank of Shamrock, a Creek County oil boomtown that had been in a decline since the mid-1920s. They left with four hundred dollars. The following month, after Dempsey was enrolled in school at Fort Smith, they pulled off two more robberies. On September 8, they took $1,743 from the Morris State Bank, and on September 29, they robbed the First National in Maud of $3,850.
The Maud holdup was one of their most successful. Choc and Birdwell, armed with a submachine gun and revolvers, got in and out of town with relative ease. Local police were fairly certain George Birdwell was one of the armed bandits, and bank employees identified the other when they were shown a photograph of Charley Floyd. The following day, Sequoyah County Sheriff George Cheek and some other law officers near Sallisaw confronted Choc and Birdwell when the bandits visited some of the Floyd relatives. There was a brief exchange of gunfire but both suspects were able to speed away. The frustrated law officers swore up and down that they had shot point-blank at Charley, and yet somehow he got away untouched. This led to the conjecture that Pretty Boy must have taken to wearing a bulletproof vest or body armor.
Despite the narrow escape, the same pair again robbed the Bank of Earlsboro for the second time on October 14. This time, they took $2,498. Talk began to circulate about the Pretty Boy Floyd gang, but most people knew that small-town bank bandits like Floyd and Birdwell had a backwoods style that in no way resembled the operations of gangsters such as Arthur “Dutch Schultz” Flegenheimer, Jack “Legs” Diamond, and Al “Scarface” Capone. The absolute lord of vice, Capone spent more money in a single hour than Choc and Birdwell took in a dozen bank jobs. Charley Floyd and his accomplices never created multileveled criminal organizations such as those managed by mobsters, racketeers, Mafia families, and beer barons in the cities. Choc simply had a style that reflected the nineteenth-century criminal traditions of the Old West.
As the economic collapse of the nation intensified, Charley and Birdwell continued their spree. On November 5, they held up the First National Bank off Conowa of $2,500, and six weeks later, they went back to Okmulgee County and took $1,162 in another robbery of the Morris State Bank. Choc joked with some of Ruby’s relatives that the Morris Bank had once turned him down for a loan when he was trying to get enough money together to buy Ruby a ring. Because of the bank’s rejection, he took great pleasure in making “withdrawals” from that particular financial institution.
Choc and Birdwell’s method of operation in these holdups was the same. They arrived in a small town during broad daylight and drove right up to the bank.
While the getaway driver kept the motor purring, Choc and Birdwell entered the bank and announced their intentions. They never wore masks or disguises. Choc was always well dressed in a suit and tie, with his shoes shined and hair slicked back, perhaps feeling that he had now a true public image to maintain. Sometimes he had on a cap, and he often wore gloves. Birdwell’s trademarks were his cowboy hat and boots. They went about their work in a businesslike manner, and after they had the money in hand, they left with two or three bank employees. These hostages were ordered to ride on the getaway car’s running boards, so no local cop would get any notions about becoming a hero and take potshots at the bandits.
“Hold on tight, and don’tcha worry,” were Choc’s cavalier words of advice to the terrified tellers or bank officers as the automobile tore out of town.
A few miles down the road, the car eased to a stop and the bank employees hopped off. They watched Choc and his pals disappear in the proverbial cloud of dust. Sometimes Choc stuck his head out of the window. He would bid the hostages farewell and gallantly tip his cap. Most witnesses reported that the bandits minimized gunplay and appeared to go out of their way to avoid violence.
One of Choc’s favorite locales for hiding his portion of the booty was at his brother Bradley’s in Earlsboro.
“Course, ol’ Choc was always welcome around our house,” recalled Bessie Floyd. “He had to kind of hide out, ya know. One time he stayed shut up in our place for ’bout a week. Nobody knew he was there and then one morning just after he took off, the biggest string of cars came out there, and we just couldn’t imagine what they were doin’. But when they pulled up, we saw that they were laws and were huntin’ their Pretty Boy. They ’bout scared my little son Cleatus half to death. He was cryin’ and carryin’ on so much that Wayne or Bayne—one of those twin boys—jumped up and yelled at those laws, ‘Hey, why don’t you fellas take those guns, and get off in a field and kill a rabbit and get off our land!’ Bradley made the boys hush up.”
Despite the constant fear of such visits, Bessie and Bradley’s sons enjoyed having their Uncle Charley visit them. Their father would hide Choc’s guns and automobile, and their mother helped Choc divide up his loot on the kitchen table and bury it in gallon syrup cans out in the yard. Much of the money would be in the form of coins. No matter how large or small the take, Choc always gave his family and often some of his friends a share of the money to help with groceries.
“I always liked it when Choc came to our house,” said Bayne Floyd. “He’d take me places with him, and when we were driving down those country roads, he’d let me drive that old Model T car. Sometimes Ruby would be with him, and we liked her. She was a jovial person.”
Glendon Floyd also had pleasant memories of Ruby Floyd. “Even though she divorced our uncle, we never gave up on Ruby,” said Glendon. “She was a Floyd, and once you’re a Floyd, you are family. That is just the way it is and always will be. She may have fallen out of favor with some, and a few of the other kinfolk may have rebuffed her, but not our part of the family. We accepted her just like we did his girlfriend, Juanita.”
Between bank jobs and after the money was divided, Choc headed for Fort Smith to be with Ruby and Dempsey. Each homecoming was a grand event. He would stop to buy gifts, and there would also be a box filled with jars of sorghum and jelly or fresh produce from relatives and friends.
“It was always like Christmas when my dad came home,” said Dempsey Floyd. “He’d wait and come in at night so people wouldn’t see him, and he and my mother would wake me up, and he would have presents for me. He brought me puppies on two different occasions, and there were always candy bars and all sorts of toys. One time, just after he made a pretty fair haul at a bank, he had me go into his bedroom and fetch a sack of money he had hidden there. ‘If you’re big enough to bring it to me, it’s all yours,’ he told me.
“Sure enough, there was a big sack under there and it was mostly coins. It was real heavy, and I had to strain and really work hard to drag it to him. He kept his word and gave it to me, but he told me to keep it hidden and use it if I ever wanted to treat my friends or buy myself something. The sack was filled with nickels, dimes, quarters, and half-dollars, and I dragged it into my room and hid it in the closet. I got pretty popular with the other kids. I’d take everybody to the show to see the latest movies, and we’d go to the ice cream stand for cones, and I’d also buy candy and pop for everyone. But all good things come to an end, and one day my mom figured out I was up to no good, and she looked around and found that stash of money I had. She took it down to the bank, had it converted into folding money, and went to a department store and bought me a bunch of new clothes, including a fancy suit with short pants. I hated short pants and didn’t want to be called a sissy, but by golly I wore them.”
After a whole host of days that might have seemed like Christmas, the real holiday arrived joyfully in Fort Smith at the end of 1931. Charley and Ruby gave each other rings. Charley cherished the cameo ring he received, and he wore it everywhere. Ruby’s gift was as prized as the pocket watch Choc always carried. The fine timepiece had been a gift from Bill Miller, his old running mate who had been shot and killed in Ohio. Attached to the watch fob was a fifty-cent piece dated 1929, to commemorate the year Choc got his freedom from the penitentiary at Jefferson City.
Every day about that time when we lived in Fort Smith, my dad would get the newspapers, and there would be all these stories claiming that he had just robbed some bank in Ohio or in Kentucky or in New Orleans or up in Kansas,” said Dempsey Floyd.
“Sometimes it was actually humorous, because at the same time Dad was supposed to be in a bank hundreds of miles away, he was right there at home with us. We all knew that he had absolutely nothing to do with many of those bank jobs. What was happening was that other fellas were using his method of operation. Some even said that they were Pretty Boy Floyd when they robbed the bank. Then there were also bankers who probably robbed their own banks. We realized that Dad was taking the blame for a lot of bank robberies that he didn’t commit.”
Although he did not use the name himself, the Pretty Boy epithet was becoming well known in households across the nation. Americans had become conditioned to the use of colorful nicknames for their outlaws.
Back in the twenties, the public had rediscovered Billy the Kid, another classic Robin Hood figure. Billy was depicted as a young man out to avenge an insult to his mother and the death of his employer. Written by Walter Noble Burns, The Saga of Billy the Kid was published by Doubleday in 1926, and its selection by the Book-of-the-Month Club confirmed the romanticized youth’s status as a mainstay of popular culture in the 1920s and 1930s. In the 1930 movie Billy the Kid, the skinny boy from New York City who became an icon of the Old West was lovingly portrayed as a frontier superhero by Johnny Mack Brown. It was a far cry from the dime novels published between the 1880s and the early 1900s in which Billy the Kid was described as a bloodthirsty killer.
During the Great Depression, a new generation of wanted men and women emerged. Some were like Choc Floyd, a young man who was rooted to the lawless history of the country he knew best. He paid close attention to the past and recalled with marked reverence the old sayings of desperadoes such as Emmett Dalton, the outlaw who survived the Coffeyville fiasco and years spent on the scout. Dalton married a Bartlesville, Oklahoma, lady named Julia Johnson and moved to California. He ended up in the real estate and movie business in the early 1920s.
Absolved of his high crimes and completely reformed in his old age, Dalton penned, with some collaborative assistance from Jack Jungmeyer, a colorful and folksy book entitled When the Daltons Rode. It was published by Doubleday in 1931, and, according to Floyd kin, served as a source of inspiration to Choc while he lolled around Fort Smith and plotted future bank robberies. The book told of many of Dalton’s earlier exploits and some of the descriptive passages fit the new breed of criminal, like Choc Floyd, who was trying to take his place.
An outlaw’s got to be cagey as a coyote to live even a short time in the land of his father. The alert outlaw acts a good deal by intuition. His wits and sense become acute as a wild animal’s. The ordinary pitch of the faculties is not sufficient. His life constantly depends upon the accuracy with which he judges men. After this has to be snap judgment. He may never have time to rectify it. He must be able to read unconsciously tell-tale signals in the flicker of an eye, the tone of a voice, the movement of a hand. The uppermost thought in the mind of every half-sane outlaw is that some day he will make a big haul and retire to the “Big Rock Candy Mountain.” An outlaw’s dying command, “Don’t surrender! Die game!”
In days past, the outlaw’s horse was his most treasured possession. As Dalton put it, “He [the horse] was fed before the man ate. His feet were zealously shod. He suffered no saddle sores, and the slightest ailment was immediately treated.” Modern desperadoes put their love and attention into the care of their automobiles. The engines had to be well tuned, and the tires in good shape so the cops and deputies could be outdistanced on the open dirt highways and gravel roads. Dalton also prized his guns—the tools of his trade—and he kept them immaculate as a child going to Sunday school. The weapons of the thirties had improved, but the love and care had not diminished.
Dalton and the other old-timers lived by an unwritten code of survival. It was also a code with taboos, such as not giving the other fellow away. The idea was “to protect a comrade even at the cost of death.” Dalton said the unspoken silence in a lawless clan was a social bond. “It is as imperative among the machine-gunning gangster of the skyscraper frontiers as it was among the spurred brigands of the open. It becomes a boasted virtue, and sometimes the cost of maintaining the code is heavy.”
Although, as his relatives pointed out, Choc was not exactly an ardent reader, he did stick it out with the Dalton book and read as far as the final chapters. Choc undoubtedly got a chuckle over some of the elderly man’s comments about the younger outlaw prototype, whom he called “the kid-glove bandit, a courtly figment of popular fancy.”
Generally, the crusty old Dalton believed the 1930s-vintage bandit had an easier time of it than the men who had ridden horseback and carried Colt six-shooters.
To-day [sic] the country-bred outlaw is practically extinct. Crowded places, city canyons, night clubs, and public amusement places are his cradle and his habitat. Naturally he clings to his environment. He takes his spoil close to where he spends it. And amid the millions of jostling but incurious strangers in a Chicago, New York, or Detroit he is as safe or safer than was the plains outlaw in his remote bush camp.
Charley Floyd was none too certain of his safety as he quietly ushered in 1932, however. The new year got off to a violent beginning, and, as usual, the authorities placed Pretty Boy smack in the middle of the mess. Late on the cold and gloomy afternoon of Saturday, January 2, 1932, six peace officers were slain and three others were wounded at a farmhouse near Brookline, about seven miles west of Springfield, Missouri, when they attempted to arrest two local brothers and ex-convicts, Jennings and Harry Young, for auto theft. Harry was also a fugitive murder suspect implicated in the slaying two years before of Mark Noe, the marshal of Republic, Missouri. What came to be known as the Young Brothers’ Massacre lasted only a few minutes and established a record for the greatest number of law officers then killed in a single incident in the history of the United States. Armed only with pistols, the deputies and detectives expected little resistance, but instead they stumbled into a hail of shotgun and rifle fire.
The Young brothers vanished in the surrounding countryside as reinforcements and a mob of angry citizens descended on the farm. Former newspaper reporter and publicity man Lon Scott, one of the movers and shakers behind the promotion of U.S. Route 66 in the twenties, was one of the first on the scene. As the moon was coming up, Scott stumbled over some of the dead bodies and jotted down notes. He was able to provide some of the more graphic and accurate reports of the carnage and pandemonium as the rabble broke into the Youngs’ vacated farmhouse. Frank Rhoades, a reporter for the Springfield Leader, was also with the first posse that swept through the darkened fields. Other news hounds with ink-stained fingers soon appeared like a horde of locusts.
The scene of the crime brought back memories of the gun battle fought on a chicken farm a few miles from the nearby Ozark town of Branson, Missouri, a little more than a year before. In that engagement, officers had shot notorious bank bandit Jake Fleagle—the “Wolf of the West”—during his attempt to avoid arrest. He was taken to a Springfield hospital, where he died. Unlike the Fleagle skirmish, the fight with the Young brothers ended in favor of the outlaws.
News bulletins about the appalling slayings of the law officers in the Missouri Ozarks were first broadcast by KMOX radio from St. Louis. They made the early editions of the January 3 newspapers across the nation. The story of the besieged bad men killing a half dozen lawmen upstaged all other news. Acts of violence involving guns and outlaws always sold newspapers, especially if editors could figure out a way to insert a colorful and recognizable name in the headline or copy. In this instance, Pretty Boy would do just fine.
Based almost solely on the fact that Charley Floyd had served his hitch in the Missouri penitentiary at the same time as Harry Young, the name of Pretty Boy Floyd was almost immediately placed high on the list of murder suspects in the bloody slaughter. Early news reports from Missouri and a wire story out of Oklahoma City quickly implicated Choc.
OKLAHOMA CITY, Jan. 2, (AP)—Oklahoma authorities, notified of the killing of six Missouri officers near Springfield, Mo., tonight, pondered the possibility that one or more of a gang of Oklahoma desperadoes, known to have been active for more than a year in the eastern part of the state, may be among the slayers.
Charles (“Pretty Boy”) Floyd, leader of the gang, is wanted on murder and bank robbery charges in several middle western states. A series of bank robberies in Oklahoma and nearby states in recent months is generally believed to have been the work of Floyd and his aids.
Officers have been informed time and again that Floyd carries two machine guns in his automobile, one of them demountable, and that he wears a steel jacket for protection.
Headlines screamed with conjecture and speculation.
SIX OFFICERS SLAIN,
THREE WOUNDED IN
SANGUINARY BATTLE
OKLAHOMA DESPERADOES
MAY BE AMONG SLAYERS
ONE OF THE KILLERS
REARED AT SALLISAW
Another wire story spoke of Oklahoma peace officers with pistols at the ready spreading the search for Choc Floyd. “The steel-vested desperado is noted for the breakneck speed at which he drives and the machine guns which are always with him,” reported the Associated Press.
Missouri Governor Henry S. Caulfield put up rewards for the apprehension and conviction of the killers and ordered out National Guard troops, including an artillery battery form Springfield, to help bring down the Youngs and any of their accomplices. Texas Rangers, acting on instructions from Texas Adj. Gen. William W. Sterling, scoured the Mexican border crossings and federal agents looked for the suspects in Tulsa, Oklahoma City, and Kansas City. Rumors spread about the whereabouts of the killers, fueled by the tabloids; the hunted men supposedly popped up in the northeastern Oklahoma towns of Quapaw and Picher, where Mickey Mantle’s father worked the lead and zinc mines. The proprietor of a Kansas City tire shop told officers that a man he identified as Pretty Boy Floyd drove a mud-splattered car carrying a wounded passenger that stopped at his place of business.
Even Chief of Police Carl Galliher from Bowling Green, Ohio, got into the act. Still angry because of Floyd’s involvement in the Bowling Green gun battle that ended with the deaths of Bill Miller and one of his police officers, Galliher told Springfield authorities he definitely believed Floyd was one of the killers they sought.
Witness accounts emerged from Texas that the two Youngs had been seen there. The spotlight turned south of the Red River. Finally, on January 5, the Young brothers, tired of running and hiding, and not wanting to return to prison, decided to end it all. They shot each other to death in a small cottage on Walker Street in Houston, Texas, in order to avoid capture.
“We are dead; come on get us,” Houston police officers heard one of the brothers yell above the din of gunfire and through the tear-gas fumes. Seconds later, there were more shots from within the cottage. Later that day, the Springfield police announced that they now believed the Young brothers had acted alone in the massacre and were the only two at the farmhouse the afternoon of the raid and shootout.
“I am very positive that only the two were at the farmhouse,” said Springfield Chief of Police Ed Waddle.
Fifty-one years after the massacre, the Young boys’ sister, Vinita, told newspaper reporters that Choc Floyd had visited the family on two different occasions after her brothers were hunted down and died in Houston. She and her mother had always contended that Harry and Jennings had no help with their slaughter of the lawmen.
“He [Choc Floyd] came by to see us, and stayed a few minutes,” Vinita told the reporter. “He said he wanted to know what happened. He probably just read about it and wanted to see the place.”
Although he was clear of any involvement in the slayings of the Springfield law officers, the news stories that contained official denials of Floyd as a participant were not nearly as prominent as earlier stories. They contributed to his celebrity, which was fast becoming mythical.
In another seventeen months, Charley Floyd would be named in yet another massacre of lawmen. By 1933, federal agents of the Bureau of Investigation would be involved. J. Edgar Hoover, the diligent and ambitious bureau director, had already become Depression-era bank bandits’ nemesis. He would not rest until Pretty Boy Floyd was hunted down.
The Young Brothers’ Massacre was a portent of things to come.