By early 1932, the “cruelest year of all,” the legend of Pretty Boy Floyd was being chiseled into stone. The notoriety made Charley as happy as a dog with two tails, but there was also a definite down side to being the center of attention. He remembered that out in the barnyard, the rooster that crowed the loudest and shook his tail feathers one too many times often ended up in the fox’s mouth or in the stew pot. The best way for a bandit to ensure that he died in bed of old age was to keep a low profile and stay in the shadows.
There were no shadows that year for Charley, however, save for the dust storms that gathered in the prairies and stirred the bowels of hell. As far as the tabloids were concerned, Choc Floyd was the cock of the walk. It was his twenty-eighth year, and he was fair game for every cop and bounty hunter; even his false sightings made juicy fodder for any aggressive reporter interested in page-one by-lines on top of the fold.
Choc and Birdwell did not disappoint their doting public, nor did they eschew controversy.
On January 14, only eight days after Charley’s name was at least partially cleared in connection with the Young Brothers’ Massacre, the pair of bandits were back in the headlines. This time they were accused of robbing banks in two small Okfuskee County towns in east central Oklahoma in less than twenty minutes during a single afternoon. Again the news stories that resulted were greatly exaggerated.
Pretty Boy Floyd was identified from photographs as one of the trio who had looted $2,600 from the First State Bank in Castle, a small community located only seven miles northwest of Okemah, the county seat where folksinger Woody Guthrie was born in July of 1912.
Witnesses to the Castle robbery said that after Floyd and his companions took the money, they forced two bank officials and two customers to accompany them on the running boards of their getaway car to the outskirts of town.
While local law officers were trailing the Castle robbers, ten miles away in Paden—a town named for old-time U.S. Marshal Paden Tolbert—three unmasked men looted the First National Bank of $2,500. Two of the bandits forced five bank customers and a lone employee to lie on the floor while the third outlaw grabbed up the money. The customers were then locked in a vault and the robbers made an assistant cashier jump up on the running board of their auto as they raced out of town. The banker was released unharmed at Boley, an all-black town six miles away, and he hitchhiked back to the scene of the crime. First reports pinned the Paden crime as well as the Castle robbery on the Floyd bunch.
By that evening, the Oklahoma Bankers’ Association made formal requests to the governor’s office to call out the National Guard. The bankers were anxious for the Guardsmen “to hunt down Charles (Pretty Boy) Floyd, steel-jacketed desperado believed to have directed two bank robberies in Okfuskee County today,” according to an initial wire service story filed from Castle. “Although the banks at Paden and Castle, ten miles apart, were robbed by different gangs, officers believed Floyd, identified as one of the machine-gun robbers here [Castle], was the power behind both raids….”
Eugene Gum, the secretary of the state bankers’ association, issued a public statement that insisted that the state call out the troops and “offer a big reward for the capture of Floyd and his pals, who enforce their edicts with machine guns.” Gum attributed “a dozen bank raids” to Floyd, whose activities he said supposedly included “so-called ‘Robin Hood’ acts of charity. In return, the persons to whom he gives financial aid, shield him from the law.
“As long as he stays down there [eastern Oklahoma] and is protected as he is now, he will continue to attack banks,” said Gum, who pointed out that the Oklahoma bank holdup insurance rate had doubled effective January 11 and that the mark of fifty-one banks robbed in the state the previous year was likely to be broken in the new year. Towns of fewer than five thousand people, where most of the robberies occurred, would now be paying ten dollars per every thousand dollars in insurance, while rates would be lower for banks in the larger cities.
Choc did not mind being credited with the Castle holdup, but he denied any involvement with the robbery at Paden. He was concerned that now folks were even saying if he did not participate in a bank stickup, that he had “directed” or orchestrated the crime. This helped conjure up more erroneous perceptions of an organized gang or a criminal network that was masterminded in Capone-style by Charley Floyd. Even at the criminal level, rural folks wished to distance themselves from the vulgarity and wanton cruelty of the city.
“That day the banks at Castle and Paden were robbed was really something,” remembered Choc’s nephew Glendon Floyd. “Down at Earlsboro we heard about the two banks getting hit at the same time, and how they blamed both of the robberies on Charley. The fact was, he and Birdwell didn’t know a thing about the Paden robbery. They held up the bank at Castle and were going like hell west down the highway when they passed the guys who had robbed the Paden bank; they were headed east with a bunch of law on their trail. It was all just a coincidence.
The Floyd family began to accept the fact that Choc was now catching much of the blame for the continued rash of bank robberies during the thirties. “People would be claiming that their bank was robbed and that Pretty Boy and his friends did it, and he’d be sitting in our house,” said Bayne Floyd, laughing. “We always felt a lot of those banks were never even robbed, or if they were robbed, that the facts and the amount taken was often blown out of proportion.”
Many people always believed otherwise, but later reports from Okfuskee County officials actually helped clear Choc and Birdwell of any direct involvement in the Paden robbery. “Although three men were involved in each robbery,” the officials told reporters, “their descriptions differed, the method of robbery was different, and the automobiles used were not of the same make.” County officials also met with agents from the Oklahoma Bureau of Criminal Identification and Investigation. Created in 1925 to help lawmen combat the increasingly mobile criminals, the agency was commonly known as the State Crime Bureau. State agents sent to the crime scenes were told that witnesses at the Paden stickup had tentatively identified two of the robbers as residents of Seminole and Bristow.
“It is nothing unusual,” said O. P. Ray, assistant superintendent of the state bureau. “They have been robbing in Oklahoma at the rate of two or three banks a week. Our information is that the two robberies were by two gangs.”
On January 15, a man identified as Troy Self, of Carnegie, Oklahoma, was arrested at the settlement of Boley. He was armed with a pistol and shotgun and was taken to Paden, where he was held as a prime suspect in the First National robbery, but bank officials failed to identify him as one of the robbers. Lawmen across the state were also on the lookout for Luther Goodall, thirty-six, and Arthur Fraley, thirty-three, convicted bank robbers who had escaped the Johnson County jail at Tishomingo the day of the robberies. Goodall and Fraley literally smashed their way out of jail by knocking bricks from around one of the jail windows with a sash weight while the guards were at lunch. The fugitives had just been sentenced to two-year prison terms after pleading guilty to the September 4 robbery of the First State Bank in Mill Creek. They were also implicated in other bank robberies.
Meanwhile, there were reported sightings of Pretty Boy Floyd coming from every direction. The son of a McAlester police officer told authorities that he had met Pretty Boy Floyd face-to-face at a tourist camp near McAlester the night of the twin bank robberies. The young man said Floyd had searched him for weapons and told him to keep quiet. He said he knew it was Floyd from seeing his pictures in newspapers, and that the outlaw was heavily armed and wore at least two or three revolvers. Spiro Barker, a cafe owner in Henryetta, Oklahoma, his cook, H. K. Noel, and two waitresses swore that Pretty Boy had dined at their establishment the night of January 15. They said they also recognized him from his photographs in the newspapers. Tulsa County deputies received information that Choc may also have been spotted in Bixby, the closest town to the farm where the Hardgraves resided as tenants. A news story about the Bixby sighting called Charley “the will-o’-the-wisp Oklahoma bank robber and gunman.”
It was apparent that the Oklahoma Bankers’ Association was not going to rest or stop hollering for relief until the elusive Choc Floyd was taken out of circulation. The bankers turned up the pressure several notches with the governor’s office in Oklahoma City.
Since 1931, Oklahoma had been governed by a colorful and crusty character named William Henry Murray. Born in Texas in 1869, Murray taught at a country school, practiced law, flirted with journalism, and was an unsuccessful candidate for the state senate before he moved north to Indian Territory in 1898, and settled at Tishomingo, then the capital of the Chickasaw Nation. The hard-core Democrat married into the tribe and became a citizen of the Chickasaw Nation and tribal lawyer, an expert at constitutional law, and active in politics. His experiments with growing alfalfa also earned him a nickname he kept for the rest of his life, Alfalfa Bill.
Elected a representative to the first legislature in Oklahoma after statehood, “Alfalfa Bill” Murray served as speaker of the house, was defeated in a bid for governor in 1910, and went on to win a seat in the U.S. House of Representatives. Following his defeat for reelection to Congress and another loss in a second try for a gubernatorial nomination in 1918, Murray grew weary and bitter. He disappeared from the political scene for many years and traveled extensively, especially in South America, where from 1924 until 1929, he attempted to create a utopian agrarian colony of Oklahomans in Bolivia. The experiment was risky and demanding and doomed to fail. Murray finally gave up and returned home.
Despite his five-year absence, the people of Oklahoma had not forgotten Alfalfa Bill. The sixty-year-old maverick, also called the Sage of Tishomingo, tested the political waters and found them to his liking. In January 1930, he announced his candidacy for governor and hit the campaign trail. The third try was a charm. In the Democratic primary, he faced off against Frank Buttram, an Oklahoma City oil millionaire who shelled out big bucks for radio and newspaper advertising and billboards. Murray, careful to avoid becoming the pawn of special interests, circulated throughout the state, eating lunches of crackers and cheese and stumping as a champion on behalf of what he called “the little people”—the poor and struggling tenant farmers and sharecroppers, and the growing numbers of unemployed city workers.
Murray, a gifted orator and showman, appeared to many observers to be cut from the same cloth as Louisiana’s Huey P. Long, the colorful political power broker who also had an unusual sense of destiny.
Murray did well in the primary, won a runoff election with Buttram, and survived E. K. Gaylord’s lambasting front-page editorials in the Daily Oklahoman and the Oklahoma City Times. Gaylord also published a series of articles criticizing Murray as a slovenly bumpkin who never bathed, lived in a crude house with a privy, sopped his biscuits in syrup, and wore long underwear beneath his rumpled suits. What Gaylord had not considered was that many of the voters in the state, where farm values had greatly declined and many farms had been sold because of foreclosures or bankruptcy, identified with the down-home candidate.
In the general election, Alfalfa Bill was swept to a record majority victory and the governor’s mansion. Thousands had braved the brisk January temperatures in 1931 to watch ninety-one-year-old Uriah Dow Murray, acting in his role as notary public, swear in his son as governor. In his inaugural address, the unvarnished Murray vowed that “this is one time when Oklahoma Indians, niggers and po’ white folks are going to have a fair-minded governor.”
Aware that the Great Depression was much more than a passing economic downturn, Murray was greeted with a range of endemic problems, including mind-boggling unemployment, a multimillion-dollar deficit in the state treasury, and widespread mortgage foreclosures and bank failures. Like a sharecropper facing boll weevils and dust devils, Murray—the embodiment of a frontier politician with a touch of unwashed Will Rogers—enacted emergency relief measures, including the appropriation of hundreds of thousands of dollars to provide staples and free seed for vegetable gardens the state created on half-acre plots between the executive mansion and the state capitol building. Anticipating the Hundred Days Reforms and the New Deal legislation of Franklin Roosevelt by more than a year, Murray collected money for hungry citizens from state employees, business executives, and even donated six thousand dollars from his own salary for the cause. As the Depression intensified, Murray, a passionate proponent of states’ rights, even joined with other governors in calling for a national relief program backed by federal funds—as long as he controlled the purse strings. Little by little, Murray hacked away at his long list of challenges.
In only the first two weeks of 1932, he had emerged as a national political figure and, with the exception of New York’s Franklin D. Roosevelt, had become the country’s best-known governor. Because of his populist methods, Murray was under bombardment from Oklahoma’s frustrated bankers. Alfalfa Bill had yet another thorn in his toe, a pest as annoying and elusive as a chigger in the Osage brush.
The evening of January 14, just hours after the bank robberies at Paden and Castle and following the formal request for a manhunt from the Oklahoma Bankers’ Association, the governor was collared by reporters as he journeyed out of the state. They caught up with Murray in Kansas City, where he spent a few hours while en route to Marshalltown, Iowa, to address a Democratic rally.
“Who are these Floyds, anyhow?” Murray blustered when reporters told him about the bankers’ plea for help. He did not appear overly upset over the situation, and he expressed his confidence in Lieutenant Governor Robert Burns, the acting chief executive of the state while Murray was gone.
Back in Oklahoma, Burns stopped short of calling out the National Guard, but he did pledge “money and the arms of wartime” when he and Adj. Gen. Charles Barrett hosted in Oklahoma City “a council of war in banditry,” attended by twenty Oklahoma sheriffs and peace officers. As the state officials and lawmen convened, and sheriff’s officers from a dozen counties joined with state and private investigators in an attempt to capture Charley Floyd, more Pretty Boy sightings occurred. Oklahoma City police alone answered eighteen to twenty telephone calls from persons who thought they had seen Floyd. One of them was Myrtle Dunn, a State Crime Bureau secretary, who told agents that on the evening of January 16 she had seen a sedan with a license tag that had been issued to Floyd two years earlier. She said there were five men inside the mysterious automobile. C. M. Reber, a bureau operative, speculated that Charley might have painted the tag to make it appear a later model, since no similar number had been issued. That same evening, another Oklahoma City man also came forward and told officers that he had spotted Pretty Boy Floyd driving another vehicle and that there was a machine gun inside the car.
“This is a desperate case,” said Lieutenant Governor Burns. “Floyd has terrorized the entire east central section of Oklahoma with his outlawry. Already six killings and ten bank robberies have been charged to his gang. He must be stopped.”
Burns and Barrett promised to make machine guns, automatic rifles, and ammunition available to civilian officers, and said they would put up substantial rewards in hopes of bringing down the will-o’-the-wisp bandit. No one really questioned Burns about just how he had arrived at the “six killings” he had mentioned, unless he was counting the Ohio shootouts, the Ash brothers, the Kansas City agent and bystander, and Jim Mills, the Akins man who had killed Walter Floyd and then disappeared.
“Rewards will be offered by the state and the Oklahoma Bankers’ Association,” said the adjutant general. “The national guard will not be called out but the equipment will be at the disposal of the officers. If Floyd is found and resists, the guard will aid the local officers in his capture if necessary.”
In one of the published accounts of the “council of war” meeting, Charley was described as an “elusive machine-gun raider, who has sworn he will never be taken alive, and was characterized as a bandit who imagines himself an Al Capone who has never come to a real test of the law.” The conferees vowed that they would keep on his trail until “he is killed or captured.”
An editorial published January 16 in the Tulsa World asked the intelligent question in the headline, CAN SOLDIERS CATCH BANDITS? It was pointed out in the editorial that “bank robbers travel in pairs, or in small groups, and they move fast, without known schedules or any advertising. If a sheriff or marshal or posse in the vicinity cannot get into action immediately, they have rather poor chances of catching the robbers. The case would be the same with soldiers. It is obviously impossible that soldiers shall constantly guard every bank; that would simply transfer bandit activities to property in other places.”
Regardless of the debate over the use of armed soldiers, the use of a reward was generally thought to be the best way to stop Charley Floyd. The Oklahoma Bankers’ Association matched the state’s thousand-dollar reward, and by the evening of January 17, the price on Pretty Boy’s head in Oklahoma alone was two thousand dollars. Rewards of one thousand dollars for Charley in connection with the slaying of the police officer in Bowling Green, Ohio, and a one-thousand-dollar reward from the state of Ohio because of Floyd’s escape from the train while on his way to the state penitentiary also remained valid, bringing the total to four thousand dollars.
While huge posses of heavily armed deputies and state agents hunted Charley Floyd, he defied them by driving into the town of Wewoka. Witnesses said he had stopped at a local hotel, rounded up the proprietor and the employees, and had them join him as he sat at a table and drank an entire bottle of whiskey. They claimed he had announced that he was Pretty Boy Floyd, and had shown them his bulletproof vest before driving away.
Then on January 20, Lieutenant Governor Burns, still acting as governor, received a personal threat, allegedly from the state’s most sought-after bandit. The letter, written by hand in blue ink and unsigned, was postmarked at Altus, Oklahoma, at 3:00 P.M. Tuesday, January 19. The message was brief and to the point.
Robert Burns, Acting Governor—
You will either withdraw that $1,000 at once or
suffer the consequences; no kidding.
I have robbed no one but the monied men.
Some criminal experts said it was certain that Pretty Boy was the author of the terse warning. Others doubted the authenticity of the threatening note. A couple of days later, Charley allegedly punctuated his threat against Burns with one more daring act: He supposedly visited another bank. The claim was that he was responsible for the robbery of the bank in Dover, a small farm town located near where the Rock Island Railroad crossed the Cimarron River in Kingfisher County. The main force of law officers after Charley had centered their search many miles to the east of Dover in Muskogee County, where there were also stories of Floyd appearances.
PRETTY BOY LOOTS STATE BANK, blared the headline in the Muskogee Phoenix on January 22. Immediately, the deputies and others in the posse who had used Muskogee for a headquarters left for Dover.
“The determined search for Charles Arthur ‘Pretty Boy’ Floyd centered tonight near Dover, where Oklahoma’s outlaw is believed to have defied the law once more by robbing a country bank there,” said the Phoenix story. “Floyd was identified partially by the bank’s cashier, A. L. Lash, as bandits entered the bank, a state institution, locked four customers in the vault, kidnapped Lash and escaped with about $700 in currency.”
Lash was released unharmed a mile and a half north of Dover. “The man driving the car resembled Floyd,” Lash said. “I’ve seen the outlaw’s picture enough to know him by sight.”
Although the constant stream of rumors helped keep the authorities running in circles, Charley did not welcome all the attention. He was not totally ego-driven. In a strange way, he only wanted to rob banks quietly, and with as little fuss as possible, and then go home to Ruby and his boy or spend an occasional lost weekend with his girlfriend.
On Saturday, January 23, the day that New York Governor Franklin Roosevelt made clear his intention to enter the presidential race, C. M. Reber, of the State Crime Bureau, appeared in Oklahoma City with what he considered to be valid information picked up on the criminal grapevine: Charles Floyd was willing to surrender to Oklahoma officers. According to Reber, there was one stipulation: Floyd did not want to be turned over to the authorities in Ohio and face the murder charge in the death of Officer Castner at Bowling Green. Floyd wanted to stay in Oklahoma. Governor Murray’s office refused to bargain with the bandit and the offer was rejected. The search continued. Much of the time Charley was sitting in his new home.
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 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 story 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 the 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 Bela 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 much 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 then handed her the money to cover three tickets.
“Choc just shoved Jackie ahead of him and we went in,” said Ruby.
Besides the movies, there was other entertainment. Each evening, the magic of radio brought into everyone’s home Tom Mix, Ed Wynn, George Burns, Gracie Allen, and a Jack Benny who had not yet reached his perpetual thirty-ninth year. There was the distinctive voice of Walter Winchell, that nasty sultan of gossip and a good friend of J. Edgar Hoover. “Good evening, Mr. and Mrs. America and all the ships at sea.”
Americans that year were more despondent than ever. There were almost seven hundred thousand people out of work in Chicago alone, and many more in New York. In Ohio—one of Charley’s preferred hunting grounds—the situation was grim. In 1932, at least half of the work force was jobless in Cleveland, 60 percent were unemployed in Akron, and 80 percent of the workers in Toledo were idle.
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 the 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.
An hour after the gun battle, the alleged offenders’ car was found abandoned at Thirteenth Place and the Katy railroad tracks. Bullet holes in the car from previous shootouts had been filled with putty and painted. Officers found an extra license plate in the automobile with the same number as the plate on a car used by thieves who robbed the bank in Konawa, Oklahoma, down in the oil patch south of Seminole, three weeks earlier. Floyd and Birdwell were the chief suspects in that robbery.
According to one account, a tag attached to the car battery of the abandoned vehicle led investigators to a garage, and from there to the Floyd residence on East Young. Another version had Detectives R. B. “Blackie” Jones and Earl Gardner following two men on foot to the Floyd house after the officers saw the pair emerge from the Midland Valley right-of-way near Apache Street. The lawmen kept their distance and then reported back to headquarters. A plan of action for a raid was developed. An informant in the neighborhood also reported to the police that he believed Pretty Boy and a companion were living on East Young. According to police, the informant told them that “they [Floyd and Birdwell] have been going into and out of the house at all hours of the night and early morning. They always drove a block or so before they turned on their lights. They came in early Monday morning after the battle with police on North Peoria Avenue.”
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 had only 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 dark 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.
The headline in the February 12 Tulsa World was an embarrassment to the local police: OFFICERS FOILED BY “PRETTY BOY” IN GAS-BOMB RAID.
Tulsa and northeastern Oklahoma was the center of one of the most intensive man hunts since the days of the Terrill-Kimes gangs yesterday as city, county and state peace officers concentrated here to take the trail of Charles Arthur (Pretty Boy) Floyd, accused bank robber and murderer who has escaped capture after two running gun battles and a gas-bomb raid.
Still smarting from the easy escapes of Floyd and an accomplice, believed to have been George Birdwell, whose name has been linked with the Sequoyah County phantom in many of his daring escapades, Tulsa police officials last night had taken precautionary measures to prevent the recurrence of the “mistakes” on the part of officers which are believed to have contributed to Floyd’s repeated escapes.
Thomas I. Munroe, fire and police commissioner was mortified. February was turning out to be an unforgettable month for him. A federal grand jury had just indicted Munroe on allegations that he was part of a protection ring for seven black bootleggers. By April, when the alleged payoff contact, a former police detective named R. G. Kennedy, developed pneumonia and influenza while in jail and died, the case weakened. Eventually, a jury would exonerate Munroe. For now, however, the commissioner had the federal charges on his mind and there was still the worrisome Pretty Boy, a constant irritation to Munroe and his department.
The commissioner was reluctant to discuss the mistakes made by his detectives, but he publicly promised that an additional six machine guns would soon be purchased for the department. “That will not happen again,” said Munroe. “The new gun we are ordering will use drums of fifty shells instead of clips of twelve. We are going to fight fire with fire and next time be prepared for any type machine gunner. We have the men on the force to operate the guns and they will be here within a few days.”
The newspaper also spoke of the apprehension of Floyd’s ex-wife and their young son. They had been stopped along with Clyde Chuculate, a thirty-two-year-old Floyd family friend, at the downtown bus station just a few hours after the botched raid. All three were arrested and taken to police headquarters for further questioning.
Chuculate, a member of one of eastern Oklahoma’s most respected Cherokee families was the brother of Perry Chuculate, the Sequoyah County deputy who had been shot and killed by George Kimes during a 1926 gun battle that took place on the road between Vian and Sallisaw. W. E. Wilson, the policeman who had been slightly wounded earlier in the week, interviewed Chuculate in a jail cell and tentatively identified him as one of the men in the car who had shot at him. Wilson said that the suspect would not take his eyes off the floor throughout the interrogation. Chuculate admitted he recognized Wilson, but said he could not remember where he had seen him. Wilson’s memory was clearer.
“I am sure Chuculate was in the car,” said Wilson. “In my mind, there is no doubt about him.”
At first, Ruby remained tight-lipped and even refused to tell officers her true name. “My name is Hamilton,” she told her interrogators. “Ruby Hamilton, I came here from Oklahoma City January 5 and rented the house on Young. My husband joined me three days later and remained here about two weeks. I have not seen him since. If I was married to Floyd, do you think for a minute I would admit it? Will you please get me the papers? All of them—Tulsa, Oklahoma City, Kansas City, and St. Louis papers. I want to see if they are filled with a bunch of lies.”
During their search of the Floyd house, detectives found many newspaper clippings from Seminole, Shawnee, Oklahoma City, Holdenville, and Muskogee that detailed the crimes of Pretty Boy Floyd. There were also recent Tulsa newspaper stories that discussed the two gun battles with police on the city streets. When the officers showed Jackie an enlarged picture of Pretty Boy that had been used to illustrate a story in a detective magazine, the little boy’s face brightened and he forgot to stick to his well-drilled story.
“That’s my daddy. That’s Daddy’s picture,” shrieked Dempsey as he stopped playing around the matron’s quarters of the jail and ran to look at the magazine cover.
The boy’s words were important documentation for investigators. Dempsey’s identification was the first conclusive evidence to prove it was really Floyd who had eluded the police three times in less than a week.
“I go to school,” said Dempsey, who was described by officers as “smart as a whip” and sweet-natured. “I don’t know what daddy does. He always reads the newspapers when he comes home with George Birdwell. He always has plenty of money and we have lots to eat and a radio. I’m going to be an engineer or a doctor when I grow up. Daddy wants me to go to school. That’s why we moved to Tulsa.”
After Dempsey opened up, Ruby finally admitted her real identity but gave very little additional information. “She denied that there had been another man there,” said Chief of Detectives Jack Bonham, “and declared that Birdwell was always with him [Floyd] and that he was the only man he could trust.”
Ruby refused to discuss her current marital status with Floyd. She denied that her father lived in Bixby, and would not give officers her maiden name. “It’s no concern of yours or the newspapers,” she shouted when asked whether she knew Charley Floyd was a robber. “Go away! Take that photographer out of here and don’t bother me.”
Later she calmed down and finally allowed W. H. Morgan, superintendent of the Bureau of Identification, to take her and Dempsey’s photograph. A newspaper photographer managed to grab a couple of quick shots, as well. Ruby and her son spent the night in jail as extra officers assigned to guard all the entrances stayed on alert for Pretty Boy in case he tried to come to the rescue.
On Saturday afternoon, February 13, after being held for more than thirty-six hours, Ruby and Dempsey were released from police custody. A squad car drove them to their residence. The officers helped Ruby set her home in order and pick up the family belongings that had been turned topsy-turvy by investigators looking for clues that might lead them to Floyd. The police guards who staked out the East Young residence were removed. Back at the jail, Clyde Chuculate, who had also remained under lock and key for a day and a half, was cleared. He, too, was set free and no charges were filed.
Police were still on the lookout for Pretty Boy. That same day, a terrified black laborer named Tom Montgomery burst into the Tulsa County sheriff’s office to report that he had been approached by some men, including one who he believed was Pretty Boy, one mile west of the Kennedy golf course on Edison Street. Trembling with fear, Montgomery related his story in gasps to the anxious deputies. He told them that he had been walking along Edison when a light-blue Buick sedan pulled up alongside of him.
“They told me they had a flat tire and wanted me to change it,” said Montgomery. “‘No sir,’ I said, ‘I’m too busy and am going places.’ Then two fellows open the back door and shoved awful long cannons at me. ‘Nigger,’ they told me, ‘you change that tire fast.’
“I told them I wasn’t going anyplace in particular and that I certainly would be glad to change the tire. I changed it in no time. Then one of them gives me a cigar and off they drive.”
Montgomery had been too frightened to notice the license number of the automobile, but he did see at least three “choppers,” or submachine guns, in the backseat. From the stack of criminal photos the deputies showed him, Montgomery selected those of Floyd and Fred Barker, a fugitive killer of a Missouri sheriff and one of four brothers raised as criminals by the mean-spirited Arizona Donnie Clark Barker, a Missouri native who ruled her lawless clan with an iron hand and came to be known as the notorious Ma Barker. A second tip also linked Floyd with Barker, but officers who went to Freddie Barker’s West Tulsa home found nothing, and Pretty Boy’s association with Barker was discredited.
Detectives also drove out Route 66 to Chelsea, Oklahoma, in neighboring Rogers County, after they obtained information that Floyd and two companions were there having their automobile serviced by a local mechanic. When they reached Chelsea and located the garage, however, they found that the three men had actually been tourists en route to St. Louis.
Officers were posted on the road leading in and out of Tulsa, especially on the highway leading to Sand Springs, where there were several reports that Pretty Boy Floyd had been seen driving through the countryside. In Tulsa, a youth identified as R. G. Nathan was arrested at an East First Street boardinghouse when officers got word that he was a suspicious character. A search of his room turned up a suitcase filled with newspaper clippings about Floyd and his exploits. After intense questioning, the officers concluded that the young man was just another one of Pretty Boy’s growing number of fans.
Evidence connecting Pretty Boy with recent robberies and killings in Kansas City also surfaced. Ballistics experts said that a bullet that had killed O. P. Carpenter, a Kansas City detective, at dawn on February 8 during the attempted holdup of the Mercantile Trust Company in Kansas City had been fired from the same submachine gun that had wounded Officer Wilson during the February 10 gun battle on North Peoria in Tulsa.
Victor Maddi, of Kansas City, had been arrested in Houston on February 11 and held as one of the participants in the Mercantile Trust robbery. The ballistics report and the arrest of Maddi strengthened the belief of Kansas City investigators that the brush with Tulsa police had occurred during the suspect’s flight from Missouri to Texas. Shortly after the Kansas City robbery, dispatches stated Floyd was part of the robbery team. However, despite the ballistics data and Floyd’s alleged relationship with Italian criminals in Ohio, most Kansas City officers concluded that because of the timing discrepancies and because he had no history of ever operating with the Italian gangsters in Kansas City, Floyd was not involved. Nonetheless, there were press reports with headlines such as MISSOURI KILLING INVOLVES FLOYD.
On Sunday, February 14, hundreds of curious motorists celebrated Valentine’s Day by slowly driving past the frame house on East Young. Since the address had appeared in the newspapers, everyone was interested in seeing the current home of Pretty Boy Floyd. Ruby and Dempsey retreated to her father’s home for a few days to avoid the unwanted attention.
The press had a field day with young Dempsey. A mawkish front-page editorial appeared in the Oklahoma City Times. Illustrated with an inset photograph of Dempsey Floyd (“…his head finely shaped, his eyes frank and finely set, his chin square and full of character”), the editorial, written by Walter M. Harrison, was addressed to Charles Floyd, and was to serve as an appeal to the phantom bandit and Oklahoma’s public enemy number one. Harrison wrote:
Desperate killer though you may be, you remain a hero to one human being in this world. When Jackie, your 7-year-old son, identified your picture as ‘my daddy,’ he spoke with pride of possession. He knows your strong arms, your rough play. He tingles with happiness when he sees you coming and he wonders why you go away so unceremoniously and stay so long.
He is innocently proud of you who have treated him so badly. With the blind devotion of every lad for his pater, Jackie now tries to walk like you, to talk like you. He has his hair combed like you comb yours and he is dreaming of the day when he can be a big man like you and go out into the big world after breakfast in the morning and never come back until suppertime.
This picture of your kid gave me a jolt. He is the stuff from which the future is made. He may have the making of a great merchant prince. But you have just about pitched his chances away.
Today you flee from the law. At the end of the trail for you, there is probably a little run in the open for the shelter of a thicket, the bark of a posseman’s rifle and a lifeless fall. A pitiful end for the father of a fine son.
Walter Biscup, a top writer for the Tulsa World and later the editorial page’s editor, had a valentine all his own for the readers. In a big Sunday feature article filled with factual errors and innuendo, Biscup presented an entertaining profile of Charley Floyd beneath a banner headline: ‘PRETTY BOY’ LEARNED HIS DEADLY TRADE FROM EASTERN GANGSTER. Biscup did say that “in fairness to Floyd,” he was not present when six law-enforcement officers were killed near Springfield, Missouri. “That was one opportunity he missed,” said Biscup.
A physical description was included, down to the Red Cross nurse and rose tattooed on Charley’s left forearm and the four gold caps in the upper front teeth. The article also contained the tally of Charley’s crimes to date, and there were more quotes from Eugene Gum, secretary of the Oklahoma Bankers’ Association.
“He is the sort of criminal who must be killed before he is captured,” warned Gum.
The spokesman for the enraged bankers did not say why there was a need to “capture” a bandit once he was dead. Biscup’s own words, especially the lead paragraphs, were the most melodramatic of all the indictments against Floyd, however.
Crime has selected him as the headman in it’s [sic] carnival!
With a submachine gun nestling in the crook of his left arm and purring an uncontrollable message of sudden death to its objectives, he is acting his part with a macabre flair of seriousness.
Thus pictured in the minds of hundreds of detectives and policemen, Charles (Pretty Boy) Floyd, worth $5,000 dead or alive, struts arrogantly to the forefront of the southwest’s present day battle with lawlessness.
From an insignificant start as a small-town bad boy Floyd has suddenly emerged into full bloom as a homicidal bandit who gives promise of making the legendary tales of the exploits of Al Spencer, Henry Starr and Matt Kimes sound like bed-time stories.
Biscup’s closing sentences sounded much like the funereal warning contained in the Harrison editorial. “Here today, there tomorrow, ‘Pretty Boy’ continues on his rampage unmindful of the fact that every officer’s gun is trained on him. He is half way down the road and cannot turn back.”
Wherever he was that Sabbath morning—safe for the moment cleaning his weapons and planning future escapades at one of his invulnerable refuges—Charley Floyd probably would have agreed. Biscup was correct. Choc could not turn back. All possible exits from a life of crime appeared blocked. The rest of his ride down the road that lay ahead looked to be very bumpy. Only a miracle could save him. And, in 1932, all the miracles had shriveled up with the crops.