Pretty Boy Floyd

Charley “Pretty Boy” Floyd (February 3, 1904-October 22, 1934) was a bank robber during the Public Enemies Era (1933-1935). Tiring of the harsh existence and drudgery of farming, he left his wife and newborn son at home and looked for better employment opportunities outside Oklahoma. Robbing a bank, he was arrested after flashing around money, and spent three and a half years in prison, where he learned the science of robbing banks. After his release, he partnered with George Birdwell to rob numerous banks in Oklahoma until Birdwell died during a shootout in November 1932. Floyd had become notorious in Oklahoma, but was still able to make frequent visits to his family. However, he attracted national attention when it was learned that he had arrived in Kansas City the evening before the Kansas City Massacre, a failed attempt to rescue bank robber Frank Nash, which left four lawmen and Nash dead, on June 17, 1933. Hoping to wait out the attention, Floyd hid for a year in Buffalo, New York. When the FBI announced on October 11, 1934 that he was considered a major suspect, Floyd tried to reach the safety of his family in Oklahoma, but was fatally wounded trying to escape a group of FBI agents and local police officers in East Liverpool, Ohio on October 22, 1934.

Early Life

Charley “Pretty Boy” Floyd was born in Georgia on February 3, 1904, the second son of seven children. Even though the Floyds had lived in Georgia for generations, his family moved to Oklahoma when he was seven-years-old because Georgia was still recovering slowly from the Sherman’s March during the Civil War and Reconstruction. Oklahoma offered opportunity for recently arrived families, but it was still a rough place. Swift justice handed out by Judge Isaac Parker, the Hanging Judge, during the late 1870s and 1880s had helped tame the area, but the eastern half of the state was still a refuge for outlaws, and Floyd grew up on tales of desperadoes and vigilante justice, developing a particular admiration for Jesse James. Oklahoma was a dry state, but many people, including Floyd’s father, distilled their own moonshine, both for themselves and as an additional cash crop.

Like the rest of his brothers and sisters, Floyd’s part-time education ended when he was a teenager. Both he and his parents thought that there was no need for more education than elementary school, and once he was an adolescent, it was time for him to start thinking about the future. He had already gained a reputation as a tough kid who would stand up for himself.

The harsh existence and drudgery of farm work held little attraction for teenaged Floyd. Having heard stories of the outside world from returning veterans, Floyd wanted to see the excitement in big cities like Tulsa, Kansas City and Fort Worth. Actually, like most young men, he did not know what he wanted but he did know that he did not want to be a tenant farmer like his father, tied to the soil and a backbreaking existence.

At the same time, resentment against the business class spread through rural Oklahoma after both cotton and coal prices plummeted following the end of WWI, forcing farmers to lose the farms and coal miners to lose their jobs. While legal money-earning opportunities were declining, the introduction of Prohibition in 1920 meant that small-scale production of moonshine for neighbors suddenly offered large-scale business opportunities. Most of the local law enforcement agents were either kin or friends, and could be relied on to look the other way. The few law officers who took the enforcement of Prohibition seriously found that farmers/moonshiners like Floyd’s dad did not back down in the face of authority.

Shortly after the surprise election of Warren Harding, which signaled voters’ desire for stability after sudden change, sixteen-year-old Floyd left his family and decided to see more of the world, supporting himself by hiring on for harvests. A hard-worker, he had little trouble picking up odd jobs to support himself until he joined a harvest crew that moved from harvest to harvest.

After harvest season ended, he lived in Wichita, Kansas in the winter of 1921. With a population of 80,000 and electric trolleys, Wichita was a new experience for Floyd.

Floyd became an acquaintance of the city’s most notorious fence and bootlegger, John Callahan, who would arrange hideouts for bandits for a fee, but he managed to avoid a criminal record during his stay in Wichita before he returned home to celebrate his eighteenth birthday. However, he would not stay for long. Although happy to see him, his family worried that he had changed, and had fallen in with bad influences. Farmers distrusted the cities and their corrupt influences on the youth, even though growing urbanization was part of the national change following WWI. This distrust of change fueled the rebirth of the KKK, which targeted visible minorities, Jews, Catholics, criminals, and even doctors who performed abortions, or store owners who cheated people.

Floyd and some friends robbed the town post office on a dare, but found that it was a federal crime because it was a post office. Floyd avoided jail only because the investigators were masons and believed the alibi provided by Floyd’s father, a fellow-mason.

Many farmers did not trust banks because hundreds of small banks failed every year during the Roaring Twenties, and most of those banks were located in small farming towns. The high interest rates charged by rural banks drove many farmers into bankruptcy. However, the bankers also realized that the dependence on cotton as a cash crop was destroying the farmland, so they tried to convince farmers to diversify their crops and to persuade the local governments to send agents to introduce modern farming techniques, but these efforts failed, since the farmers did not listen to the college-educated agricultural experts. Instead, when farmers lost their farms, they became tenant farmers (sharecroppers), and they planted cotton on every inch of their farms to increase their crop, even sacrificing their own vegetable gardens.

At the same time, roughly sixty to seventy banks were robbed every year during the twenties. Faced with drastically rising insurance rates, the banks increased security but people still viewed the banks as the enemy, who cheated them on a regular basis, and robbers as heroes. Large groups of people believed that there was nothing wrong with robbing a bank as long as it was insured and nobody got hurt.

In 1923, Floyd had started seeing Ruby Hardgraves, the daughter of a sharecropper, who was three-years-younger than him, and they were young, in love, and clearly not waiting for marriage to have sex. She realized that she was three-months pregnant in May 1924, and they were married in June. The baby was born in December, and Floyd was bursting with pride in his newborn son, Charles Dempsey Floyd. However, he was still tired of the limitations of cotton farming, so he left in late August 1925, shortly after their first wedding anniversary, to go back on the harvest circuit.

Early Criminal Career (September 1925-February 1930)

It soon became clear to Ruby that her husband was not harvesting crops because he was sending her large sums of cash. Unknown to her, right before he had left, Floyd had traded five gallons of moonshine for a pistol. Teaming up with another young drifter named Fred Hildebrand, they rode the rails for a while, and returned in mid-September, flush with cash. Suspicious that the two young men were driving a new car, the local sheriff pulled them over, and found two thousand dollars in wrappers stamped with the name Tower Grove Bank of St. Louis. The two men were placed in jail, and the sheriff called the bank in St. Louis, learning that three men had robbed couriers carrying a payroll of $11,929. Floyd refused to confess, but Hildebrand soon collapsed and said everything. Pleading guilty, Floyd was given five years in prison.

Conditions in the penitentiary were harsh, twelve-hour workdays were standard, and floggings were common. Meals were eaten in silence. Realizing that trouble simply was not worth it, Floyd was polite to guards, and chose carefully which inmates he spent time with. He was not a model prisoner, he just wanted to get through his sentence smoothly. Given the harsh treatment, complete lack of rehabilitation, and the fact that he was surrounded by horrible men, both his fellow convicts and the guards, the five years went well.

However, Floyd took advantage of his proximity to experienced criminals who possessed valuable skills and far too much free time. Viewing Floyd as a promising young man, they shared tricks, advice on dependable lawyers, warnings about which towns had the most honest cops, and Floyd absorbed as much as he could. He needed something to keep him focused, since his wife’s letters had become increasingly bitter until she asked for a divorce in January 1929, which Floyd did not contest. He was released two months later, after three-and-a-half years in prison. Like many ex-convicts, he immediately promised himself that he would never go back.

The nation had changed, and crime was increasing as gangs fought for control of the insanely lucrative bootlegging industry. Al Capone had shot to national prominence after six members of a rival gang died during the St. Valentine’s Day Massacre in 1929.

Floyd stopped off in Kansas City to blow off some steam before returning home. Kansas City had become a wide-open town, part of a series of towns, including St. Paul, Minnesota, Detroit, Michigan, Joplin, Missouri and Hot Springs, Arkansas, that offered sanctuary to connected criminals who were able to pay for the privilege. Aside from gangsters and bank robbers, professionals like lawyers, accountants and civil servants would hold conventions in Kansas City, attracted by the opportunities to sin. After a brief visit to Kansas City, Floyd reunited with his older brother who had moved to the oil fields in Oklahoma, but it was clear that he really wanted to go back to Kansas City. The Seminole oil field was a boom town filled with rough men and a huge number of saloons, dance halls, and gambling joints happy to take their money, as well as criminals trying to take their money and their lives. It was not a place for the weak. Floyd naturally visited the rest of the family, and learned that Ruby had taken their son and moved to a different part of the state.

Floyd dutifully found a job in the oil-field but when the company learned that he was an ex-convict, he was fired because the companies were trying to clean up the oil fields. Refusing to return to the backbreaking labor of farming, Floyd decided to go to Kansas City to start a bootlegging business, but he lacked connections and was jailed by police for vagrancy. Clearly, he attracted the police’s attention since he was arrested five times in three different states in six months.

Shortly after the stock market crash, Floyd’s father was killed by a business rival after a heated argument. After helping to bury his father, Floyd returned to Kansas City, where he was finally starting to make the right connections, partially through people he had met in prison.

Floyd started rooming at a boarding house run by a former Sunday school teacher, who was nicknamed Mother Ash by the endless flow of criminals looking for a safe place to sleep. Floyd got his nickname ‘Pretty Boy’ from Ash’s daughter-in-law Belulah, who saw him all dressed up, and said “hello pretty boy, where did you come from?” He stayed careful around her since her husband was a criminal and rumored stool pigeon.

Robbing Banks (February 1930-June 17, 1933)

Floyd was making good money buying illegal alcohol in the city and selling it in the oilfields of Oklahoma. With little patience for police, crooked or not, Floyd was not popular with the local power structure, so he was easily persuaded by James Bradley and Bob Amos, fellow ex-cons, to switch to robbing banks. Another criminal, Jack Atkins, soon joined the gang.

After several weeks of scouting targets, they robbed the Farmers & Merchants Bank in Sylvania, Ohio on February 5, 1930. They were five men, including the driver, and nobody wore masks. The robbery was not a complete success, and they barely escaped with two thousand dollars. The gang did not keep a low profile and several of them, including Floyd, were arrested a month later by Akron police who thought they were bootleggers. Evidence found in their possession linked them to the robbery in Sylvania, so Floyd was sentenced to the Ohio state penitentiary for twelve to fifteen years.

Having sworn to never go back to prison, Floyd took a chance and jumped from a moving train. Surviving the landing, and avoiding the guards’ search, Floyd made his way back to Kansas City, where he hooked up with Willis Miller, a slightly younger man. The two men spent a lot of time at Mother Ash’s house, where they pursued Belulah and her sister Rose, who had left their husbands, Ash’s two sons.

When the police started raiding gambling halls after rumors spread that the Ash brothers had been arrested and had informed to avoid prison, the two men disappeared on March 25. Their bodies were found two days later, and Mother Ash was convinced that Floyd and Miller were responsible. The police thought so as well, but were unable to make a case. The two sisters started dating the two men, and the two couples traveled through Oklahoma, Arkansas and Kentucky, where they are believed to have robbed several banks to finance their trip, but there is no proof.

Locals were suspicious that the quartet was casing a bank in Bowling Green, Ohio, and when police approached them on April 16, 1931 to bring them in for questioning, the two outlaws opened fire. Miller died in the shootout, Belulah was badly wounded, Rose was arrested, but Floyd escaped. One of the two police officers soon died of his wounds. The women refused to give anyone’s correct names, but fingerprints soon identified Miller.

Wanted for the murder of a policeman, Floyd went on the run, but his girlfriend Belulah recuperated at his brother’s house after she was released. Although it is unknown for sure, it seems likely that Floyd hid out in Toledo, Ohio after paying protection to the Licavoli clan, a powerful gang in Ohio.

By the summer of 1931, Floyd had returned to Kansas City, while making frequent visits to Belulah in Oklahoma. He was caught in a raid on a liquor syndicate on July 20 in Kansas City but shot his way out. A Prohibition agent died during the shootout.

When two ex-convicts ambushed and killed six police officers in Missouri on January 2, 1932, local newspapers seized on the fact that he was a suspect and started to blame every bank robbery on him, turning him into a celebrity. Although he was innocent of the crime, Floyd embraced his Jesse James-like status and wrote a letter to the governor saying that he only robbed the rich, which was popular in poor Oklahoma. His fame grew after he survived two separate shootouts with police.

Ruby had remarried, but she left her new husband the first night Floyd came back. Floyd moved Ruby and his son into a home in Fort Smith, Arkansas, and they were a family again, although he still continued to see Bellulah.

He also continued to rob banks, having recruited George Birdwell, who robbed thirteen banks with Floyd in a little less than two years. All of the banks were in Oklahoma and they usually stole two or three thousand dollars. They would just drive up to a bank, walk in without masks, do the hold up, take a few employees as hostages, and go back to the car where the driver, usually someone brought in for that specific job, was waiting. Both Floyd and Birdwell shared their loot with family and friends.

When six policemen died during a failed attempt to arrest two brothers on January 2, 1932, newspaper editors happily linked Floyd to the brothers, even though there was no proof suggesting a connection.

On January 14, two banks were robbed in towns less than a twenty-minute drive from each other in the same afternoon. Floyd was identified in one of the raids, and the Oklahoma Bankers’ Association claimed that he had directed the other job, even though it was just a coincidence. The association was concerned that fifty-one banks had been robbed in Oklahoma during the previous year, driving up insurance costs for banks in small towns. The state government and the association each contributed $1,000 to a reward for Floyd’s capture, in addition to a reward of $2,000 in Ohio, spawning a torrent of claims to have seen Floyd.

While Floyd had initially enjoyed the attention, it was starting to interfere with his desire to spend time with his family, along with occasional visits to his girlfriend. The police finally tracked down the outlaw at his home, but the careful positioning of twenty policemen gave Floyd and his family enough warning for them to slip away on February 12. However, Ruby was caught several hours later. After several hours of questioning, she was released, but the police had obtained a great deal of evidence after searching their house.

Despite the repeated editorials condemning Floyd as a machine-gun toting desperado, he had not killed anyone during a shootout, or rather there was no proof that he was the one who had fired the bullet. That record would change. Lured by the reward, retired deputy sheriff Erv Kelley had started hunting Floyd with the permission of the Oklahoma State Crime Bureau. Following Ruby, Kelley found a farmhouse where she would meet with Floyd, and formed a nine-man posse made up of lawmen and deputized local farmers to wait near the house on Friday night, April 8. Four of the men had taken a break and gone into town to get food and coffee for the rest of the men, but Floyd and Birdwell showed up while they were gone, and killed Kelley. A massive manhunt followed, but the two outlaws managed to stay hidden even though Floyd had been badly wounded by Kelley. Floyd later admitted in an interview that he had shot Kelley when he stepped in front of the car telling him to give up.

After having his wounds patched by a discreet doctor, Floyd and Birdwell hid out for less than two weeks before robbing another bank because they had bills to pay, including doctor’s bills. He managed to elude police because country folk were clannish and refused to talk to the law, so he was able to see his family and Ruby fairly often. Birdwell was even able to briefly visit the funeral home to see his dead father during broad daylight. The two outlaws evaded a posse after a gun battle in June, and continued to rob banks, driving police and bankers in the Midwest crazy.

Floyd eluded the police at the same time that the Bonus Army camped out in Washington, and was finally driven out by soldiers led by Chief of Staff Douglas MacArthur, who had ordered the use of tear gas and the destruction of the poor people’s camp. At the same time gangster films like Little Caesar and Public Enemy were huge hits as people identified with tough men who carved out their own path to riches. Men like Floyd were popular anti-heroes and rebels against society.

Two days after robbing the bank in his home town on November 1, he gave an interview to reporter Vivian Brown, who had spent months contacting Floyd’s relatives to earn their trust so they would arrange the interview. During the interview, he admitted that he robbed banks but claimed that no one suffered since the money was insured, so only the bankers themselves lost money, ignoring the cost of higher insurance rates and the dead law enforcement officers. Brown was never able to write a book about Floyd as planned but she did produce a series of articles about him in 1934.

Tired of the endless stream of robberies, the Oklahoma Bankers’ Association posted rewards for bank robbers, offering $100 for a captured robber, and $500 for a dead one, and the association had paid rewards on 216 robbers by November 1932.

Birdwell died on November 23, trying to rob a bank in an all-black town to get enough money to pay Ruby’s hospital bills, since she had taken ill recently. Birdwell killed the bank president for pressing the alarm, and was shot by an employee. One of his partners was killed by locals and the third was badly wounded. Floyd had refused to take part in the job because he thought it was too difficult.

Following Birdwell’s death, Floyd found a new partner, Adam Richetti, the son of poor Italian immigrants who had settled in Oklahoma. Richetti grew up scrounging for money and getting into fights before graduating to robbing banks. In late 1932, he joined up with Floyd to rob a bank and they remained partners for the rest of their lives.

Having become too famous to stay anywhere for long, Floyd continued to live on the run. However, he still had his family and Ruby’s family who were always happy to host him for a day or two. Aside from kinship, people were bored and poor, but Floyd brought excitement and money.

Ruby was getting attention because she had started a traveling show where her son would come out between movies in a theatre and introduce his mother, who would talk about how crime had ruined their lives.

Floyd had become well-known in Oklahoma, but he was still able to move around without attracting much attention. That relative freedom disappeared following the Kansas City Massacre.

Although it seemed likely that Floyd and Richetti were not in the state, they were blamed for the killing of two lawmen who had performed a routine check on June 14, less than an hour after a bank robbery in a nearby town in Missouri. The entire state mobilized to hunt the killers, and a witness identified Floyd as one of the killers. It became clear that she was mistaken since Floyd’s relatives claimed he was in Oklahoma with them at the time, and the actual robbers confessed a year and a half later.

According to relatives of Floyd, he and Richetti visited Kansas City to relax for a few days with Belulah and her sister, and were unaware of the massive manhunt, otherwise they would have avoided Kansas City.

Their car broke down outside Kansas City, so they paid a farmer to tow their car to the nearby town of Bolivar, where Richetti’s older brother worked as a mechanic at the Chevrolet company. Since they were driving a fancy Pontiac and it was a small town, the company’s salesmen gathered to check out the competition. Joining the salesmen was the county sheriff, who used to be a salesman at the company, and had stopped by to chat. Richetti noticed the sheriff carefully studying Floyd as if trying to place his face and took the sheriff hostage as they left, grabbing another car instead of waiting for their car to be repaired. This was fortunate, since another passer-by had noticed them and alerted a deputy who was gathering a posse to capture the outlaws. On the way to Kansas City, Floyd talked with the sheriff, claiming that he had never wanted to become an outlaw but was driven to the lifestyle by the police, and now he knew that he would be killed, sooner or later. The two outlaws released the sheriff and the driver of another car that night (June 16) on the edge of Kansas City, where Floyd and Richetti were picked up by someone, likely Belulah or her sister.

Kansas City Massacre (June 17, 1933)

When four lawmen were gunned down just outside the Kansas City train station the next day in a failed attempt to rescue bank robber Frank Nash, Floyd was a natural suspect. However, only one witness identified him, and the FBI agents felt the evidence was too slim to make him a priority, choosing to focus on hitman and bank robber Verne Miller, who was known to be a friend of Nash. Furthermore, Floyd disappeared from public view for the next few months, so he was basically ignored by the Bureau.

Floyd swore to family and friends that he had not been involved in the massacre, and they believed him, claiming that it was not his style, and that it was just horrible timing that he was in the same city at the time. His family stressed that Floyd had never denied any of his crimes before.

Post-massacre (June 18, 1933-October 10, 1934)

Floyd’s status changed dramatically on March 14, 1934 when fingerprints from Miller’s home, which had been misfiled for months, were examined, and one of them belonged to Adam Richetti. With a suspect in the Kansas City Massacre, the FBI sprang into action. At least, Director J. Edgar Hoover ordered it to spring into action but the Oklahoma office did not have the manpower needed to follow up leads on the Barker-Karpis gang and the Clyde Barrow gang, so little progress was made at first. Moreover, John Dillinger’s escape from the jail at Crown Point on March 3 and his subsequent alliance with Baby Face Nelson meant that far more agents were assigned to the hunt for him than for Floyd.

Unknown to the Bureau’s agents, Floyd and Richetti hid with Belulah and her sister for a year in Buffalo, New York, where Floyd spent most of the time cooped up inside a small apartment.

Several Kansas City detectives believed that Floyd was not involved in the massacre, claiming it was not his nature. However, the FBI relied heavily on the testimony of a woman who stated that she had seen Floyd, although the Kansas police were dubious, since she had given an incorrect physical description. Testimony from other witnesses contradicted West’s testimony but their testimony was discounted by the FBI because they were black, even though they had identified Harvey Bailey, Wilbur Underhill and Verne Miller. Miller’s mutilated body would be found on November 29, 1934. Underhill was captured on December 30, 1933, but refused to talk before dying of his wounds a week later. Bailey was arrested on August 12, 1933, but also refused to admit to involvement in the massacre.

While Floyd and Richetti were hiding, many of the bank robbers and kidnappers Floyd had known or heard of died in shootouts or were captured, signaling that bank robbing was no longer a viable career.

Despite Richetti’s fingerprints, not a single informant was able to provide evidence that confirmed that Floyd had worked with Miller. This would change in August when Johnny Lazia, a powerful Kansas City gangster, was killed and a bullet removed from his body turned out to have been fired by the same gun that was used in the massacre. Lazia’s friends blamed a rival gangster, Michael LaCapra, who turned himself into the Kansas City Police after he barely survived an assassination attempt. Seeking protection, he told FBI agents that Miller had asked Lazia for men to free Nash, and Lazia had introduced Miller to Pretty Boy Floyd, who needed money. When Floyd was wounded in the shootout he was treated and hidden by Lazia’s men. Although it was quite possible that LaCapra had concocted a story linking Floyd to the massacre in a desperate attempt to win protection as a government witness, Hoover had no doubts.

Final Run (October 11-22, 1934)

FBI Director J. Edgar Hoover’s announcement on October 11 that Floyd had been involved in the Kansas City Massacre flushed him out into the open. Floyd had hoped that the attention would gradually die down, enabling him to return to a semblance of a normal life, but the FBI’s renewed attention meant that the hunt would intensify. Believing that he would be safer in Oklahoma, Floyd decided to return home, but their car broke down in Ohio on October 20. While they were waiting for their girlfriends to get a mechanic, a local police officer was alerted by suspicious neighbors and arrested Richetti, but Floyd got away. Eluding a posse, Floyd disappeared into wild country. Senior agent Melvin Purvis arrived on October 21 with a team of FBI agents drawn from the offices in Cincinnati, Cleveland and Pittsburgh. The sheriff who had caught Richetti proved unwilling to work with the FBI, and refused to hand over Richetti, who would face Ohio charges. Despite the lack of cooperation, Purvis sent agents all over the area. Aside from the twenty FBI agents, two hundred police and sheriff’s deputies were manning roadblocks.

A local constable had heard that a solitary man had appeared at a farm, where he was given water and a sandwich before going on his way, so he alerted the police. Hearing the news, Purvis gathered three of his best agents, and asked East Liverpool Police Chief Hugh McDermott for support, so McDermott brought along three officers. Floyd had appeared at the home of Ellen Conkle, a widow, who like most country folk, was unable to refuse a meal to a stranger, even one as ragged-looking as Floyd. After finishing the meal, her brother agreed to give Floyd a lift to a nearby town, and they had just started when two cars appeared with the agents and the police. Floyd ran out of the car and headed for the woods but the eight agents and police opened fire. Wounded, Floyd fell to the ground where he was disarmed by the police. While waiting for medical help he refused to answer questions about the Kansas City Massacre and died of his wounds before a doctor could arrive.

Aftermath

There is still no official evidence that Floyd took part in the massacre but Volney Davis from the Barker-Karpis gang stated that Verne Miller had said that Floyd had been his partner and Alvin Karpis confirmed that Floyd had told him the same thing. However, the examination of Floyd’s body did not show a wound to the left shoulder as claimed by the FBI’s main witness, James LaCapra, which weakened the Bureau’s case against Floyd.

Richetti was tried in June 1935 for his involvement in the Kansas City Massacre and the surviving lawmen swore that they recognized him even though their statements made at the time claimed that they had seen nothing. Their testimony ensured that Richetti received a death sentence and he died in a gas chamber on October 7, 1938.

Floyd had grown up when Oklahoma was still barely tamed and the local law enforcement had difficulty coping with outlaws. The Depression had initially aided the outlaws, since banks were viewed as the enemy. However, times changed and a combined effort by a new national police force, the Bureau, and state and local police took a toll on the bank robbers. The government had already won its war against the outlaws by the time of Floyd’s death, and would soon capture or kill the last few holdouts. Only nine banks were robbed in Oklahoma in 1935, and only ten banks were robbed during the four years between 1936 and 1940.

Related Movies

Pretty Boy Floyd (1960)

Directed by Herbert J. Leder, starring John Ericson and Barry Newman
Tells the story of Pretty Boy Floyd, who was involved in the Kansas City Massacre and became a successful bank robber until the FBI finally tracked him down.

A Bullet for Pretty Boy (1970)

Directed by Larry Buchanan, starring Fabian and Jocelyn Lane
Pretty Boy Floyd becomes an outlaw after killing the man who murdered his father.

Dillinger (1973)

Directed by John Milius, starring Warren Oates and Ben Johnson
Following the death of several FBI agents during the Kansas City Massacre, FBI agent Melvin Purvis vows to capture or kill a number of famous outlaws including Machine Gun Kelly, Pretty Boy Floyd, Baby Face Nelson, and John Dillinger. (full review)

Public Enemies (2009)

Directed by Michael Mann, starring Johnny Depp and Christian Bale
Led by agent Melvin Purvis, the FBI hunts outlaws and bank robbers, including John Dillinger, Baby Face Nelson, Pretty Boy Floyd and the Barker-Karpis gang. (full review)

Further Reading

Pretty Boy: The Life and Times of Charles Arthur Floyd-Michael Wallis, New York: W.W. Norton, 2011.

It is an excellent book that does not merely relate Floyd’s life story, but recreates the environment that Floyd grew up in, and explains the dramatic cultural transformation following WWI that helped create the public enemies.

Public Enemies: America’s Greatest Crime Wave and the Birth of the FBI, 1933-34. Bryan Burrough, New York: The Penguin Press, 2004.

The author grew up listening to stories about Bonnie and Clyde, and decided to write the book because there was no single history of that period, partially because the FBI files had only been released in the late 1980s. His access to previously sealed FBI files means that the story is as much about the evolution of the FBI as it is about the gangsters themselves. It is a superb, one-stop look at that brief period where outlaws seemed to roam free. Ignoring the easy approach of dividing the book into several sections that focus on individual gangs, the story is told in chronological order, which might appear confusing to some readers but serves to show how interrelated the events were. Most of the gangs knew each other and their paths crossed more frequently than I would have thought, which may help to explain why the FBI was so confused in the beginning. Burrough’s attention to detail is impressive, he shows what happened to the main FBI agents, the surviving outlaws who ended up in prison, and their various girlfriends and accomplices. What is odd is that once the War on Crime was over, no one really talked about it. The agents rarely told their families, while the families of the outlaws often preferred to move forward and leave their tainted past behind them.