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The Prohibition Era was a dangerous time in American history. The threat of gangster violence and mobster politics was so brutal that it eventually led to the creation of the FBI. During the days of speakeasies and suicide doors that dominated the early 20th century, these outlaws and bandits were celebrated by the public for their brutish and unflinching acts of thievery and violence. These are some of their stories.
Born on June, 22, 1903 in Indianapolis, Indiana, John Dillinger found a penchant for crime at a very young age. Early accounts of his childhood were riddled with fights, bullying, and run-ins with the law that were described as “bewildering” by those close to him. After fearing the city to be too dangerous, Dillinger’s father moved the family to Mooresville, Indiana, where Dillinger spent much of his adolescence. Trouble, however, was not far behind. Despite the town’s quaint atmosphere and small population, young John Dillinger grew a reputation for committing acts of theft, particularly involving automobiles.
With few options available to him, Dillinger enlisted in the United States Navy, working as a machinery repairman aboard the U.S.S. Utah. Only a few months in, however, Dillinger abandoned his post and was dishonorably discharged. In an attempt to calm his tumultuous lifestyle, Dillinger returned back to the quiet town of Mooresville, where he unsuccessfully tried to hold a steady job. When ends could not be met, however, he resorted back to old habits of crime and thievery. After a grocery store robbery went wrong, Dillinger found himself in front of a judge pleading guilty to assault and battery along with conspiracy to commit a felony that earned him nearly 10 years in prison. It was at the Indiana Reformatory and State Prison that Dillinger would cement himself in the world of organized crime proclaiming, “I will be the meanest bastard you ever saw when I get out of here.” His connections made during this time would prove useful after his release, giving him the knowledge and skillset to pull off the large-scale robberies for which he would eventually become famous.
Angry against the society that locked him up, Dillinger began plotting his next string of robberies that would lead him back to prison. After being apprehended by police in 1933 for stealing $10,000 from the New Carlisle Nation Bank, Dillinger was back behind bars, but not without an escape plan. With accomplices disguised as correctional officers, Dillinger escaped from prison and fled back to Indiana where the famous “Dillinger Gang” would make headlines for their crimes. For the next 2 years, the “Dillinger Gang” would wreak havoc throughout the Midwest, successfully pulling off 12 different robberies totaling nearly $7 million in modern currency. The process of bank robberies was now down to a science; the men in the Dillinger gang employed military-style tactics to pull off their various heists including the use of fast vehicles, powerful weapons like the Thompson submachine gun, and even bullet proof vests. Each member of the gang held specific and highly import roles during the heists. Lookouts, getaway drivers, and vault men were all strategically placed to improve chances of success. Detailed maps along with discarded cars and weapons following the crimes would confuse eye-witness as well as police, helping assure escape.
Little Bohemia, a favorite hideout of Dillinger
Dillinger and his gang may have been ghosts to the law, but to the public, they were rock stars. Dillinger’s face was printed across media outlets nation-wide to help police and investigators capture him. Because of the increased publicity, Dillinger resorted to extreme measure to elude capture and even underwent plastic surgery to alter his appearance enough to avoid recognition. Ironically, the federal government spent more money trying to capture Dillinger than he ever actually stole. Some agencies were solely dedicated to his arrest. Dillinger, along with several other criminals of the era, were the catalyst for the formation of the Federal Bureau of Investigation, led by J. Edgar Hoover. After several shootouts, car chases, and escapes from authorities in places like the Little Bohemia vacation lodge, it was an informant known as “The Woman in Red” that eventually alerted FBI agents to Dillinger’s whereabouts. This betrayal from the former friend of Dillinger’s love interest would be the end to his story. On the evening of July 22, 1934, John Dillinger was confronted by FBI agents outside the Biograph Theater in Chicago causing a foot chase down a nearby alley where Dillinger was shot and killed. His body, on display for less than 2 days, drew an estimated 15,000 people to the Cook County morgue for viewing.
A favorite weapon on Dillinger’s is well-known to be the Thompson submachine gun. In the upcoming Premier Auction, there are no less than 8 “Chicago Typewriters” available to the collecting public. Previously, Rock Island Auction Company had the distinct pleasure of investigating a Thompson and a possible connection to John Dillinger. Read the blog here.
Charles Arthur Floyd grew up poor. Because of the “Dust Bowl,” life as a farmer in the United States was extremely difficult and many families fell into extreme poverty. Not immune to the intense pressures of a crippling economy, Floyd found monetary refuge in organized crime which provided him with numerous ways to make a profit during difficult times. At the age of 18, Floyd found himself behind bars for the first time after stealing less than $4 from a local post office and was arrested again just three years later for payroll robbery. After his release, he was believed to have been involved in the disappearance of Jim Mills, a man suspected of murdering Floyd’s father. Because Mills was never seen again after being acquitted of the charges, it is highly likely that Floyd killed him. These actions would go on to foreshadow the violent path Floyd would venture down, a path that would eventually lead to his death.
Known to many as the “Robin Hood of Cookson Hills,” Floyd had a sense of poetic justice in many of his actions, with some calling aspects of his legacy warranted or even justified. Characters featured in literary works such as in John Steinbeck’s novel, The Grapes of Wrath, spoke fondly of Floyd. It was even rumored that while robbing banks, Floyd would take the opportunity to rip up and destroy mortgage documents. While certainly an enthusiast of stealing from the rich, there was another nickname attached to Floyd that he wasn’t so fond of. While some argue that “Pretty Boy Floyd” was a nickname given to him by multiple girlfriends, others attribute it to a name given to him because of the nice attire he wore while working on oil rigs. Despite its unclear origins, one definitive fact about the nickname was that Floyd hated it.
After moving to Kansas City and finding relative success in robbing banks, Pretty Boy Floyd gained unwanted attention for his crimes. When captured by authorities and sentenced to 12-15 years, Floyd escaped detention by kicking through a window on the train carrying him to prison. It was during this time as a fugitive traveling around multiple states that Floyd would gain national infamy for his violent crime sprees and the killing of an FBI agent. Eventually traveling back in Oklahoma, Floyd was the subject of state-wide manhunt with a $6,000 bounty placed on his head by the governor himself. With his reputation growing throughout the country, he sank deeper and deeper into the criminal underworld of the Prohibition Era.
After the death of John Dillinger, Floyd skyrocketed to Public Enemy No. 1 because of his alleged involvement in the Kansas City Massacre, a mass murder in Missouri that lead to the deaths of four law enforcement officers. While Floyd vehemently denied any involvement in the shooting, many of the known accomplices of the event swore he was involved, going so far as to say he confessed and was even shot in the arm during the altercation. Nevertheless, the FBI intensified their search for Floyd, convinced he was at the center of the massacre and pinning most of the blame on him in the media. Finally, on October 22, 1934, Arthur “Pretty Boy” Floyd was fatally shot when confronted in an Ohio field by federal law enforcement agents.
Pretty Boy Floyd may not have emerged victorious from that field in 1934, but the story of his legacy continues to this day. Available in the upcoming Premier Auction at the Rock Island Auction Company is a documented Colt Government Model owned by Public Enemy No. 1, Pretty Boy Floyd. Recovered by law enforcement agent, Chester Smith, this item is an amazing artifact owned by one of the most dangerous men in America.
Government Model C97206 was one of two recovered from Floyd on October 22, 1934 and is accompanied by a notarized letter from Smith stating as such. Its counterpart remains the property of the FBI and once hung on Director J. Edgar Hoover’s “Wall of Shame.” Said serial number confirms it as a 1917-production pistol and much like Floyd himself, has a rather unassuming appearance. To the uninitiated, it would appear as any number of other Colt Government Model pistols, but in the hands of a murdering bank robber it tells another story entirely. To hold it is to feel a chill knowing what this gun may have seen or been party to. In December 2018, Rock Island Auction Company had the distinct privilege of offering a Colt Model 1921 Thompson machine gun that was present at the Floyd’s final mortal moments (see video below). It brought $69,000 and was once a part of the same collection as this Government Model.
Arguably the most famous mobster of all time, Alphonse Gabriel Capone was born in Brooklyn, New York on January 17, 1899 to a family of Italian immigrants. While a promising student, Capone’s education would end abruptly after he physically struck a teacher when he was 14, leading to his expulsion. He worked a few honest jobs, but future trouble seemed inevitable. Capone became involved in several different street gangs at a very young age that were involved in crime throughout the city of New York such as the Junior Forty Thieves, Bowery Boys, the Brooklyn Rippers, and even the Five Points Gang. It was the beginning of a criminal career that would bring him nationwide fame, vast fortune, incredible power, as well as his demise.
His work became that of a bouncer at bars and brothels, many owned by organized crime organizations. By 1919, he had been invited to Chicago to take on larger roles within the mafia and by age 26 was the new boss for one of the Windy City’s largest criminal enterprises, primarily dealing in the illegal brewing, distilling, transportation, and sale of alcohol.
Violence was the tool of his trade, using intimidation to force the purchase of his liquor, forge political allegiances, bomb polling places, and murder his rivals. The most famous of the latter crimes, of course, is the notorious St. Valentine’s Day Massacre in 1929 when in an attempt to kill Bugs Moran, leader of the North Side Gang, seven members of the North Side Gang were slain in broad daylight by Capone’s assassins posing as policemen while wielding shotguns and Thompson submachine guns.
When photos of the massacre hit newsstands, public opinion turned against Capone as did Federal leniency. He was arrested by the FBI within a month, and began a string of court appearances and charges that did not cease until he found himself in the less-than-friendly confines of Atlanta U.S. Penitentiary in May of 1932.
This Colt Model 1908 pistol was presented to Mr. Karl Kahn, a respected crime reporter who worked for the "Chicago American" newspaper from the 1920s to the 1940s. He also wrote for "The Real Detective" magazine, then the nation’s most read magazine on crime in America. In his articles for "Real Detective," it is said that Kahn was very kind to Capone and thus was allowed to accompany Capone on his train ride en route to the Atlanta Penitentiary, where Kahn would eventually interview Capone for the "Chicago American."
In a notarized letter from Kahn’s widow, Mrs. Lucille H. Kahn, he was given this pistol by a member of Al Capone’s mob who accompanied Capone to the prison and likely rode with the two men.
The little pistol is appropriately flashy for a mob king who appreciated a lavish lifestyle, and the same nickel plated finish is extremely desirably by collectors today. Its matching Colt silver medallions still shine brightly on their checkered walnut grips, and the gun remains in excellent condition at about 90%. It remained in the Kahn family until the fall of 1993 when it was sold privately for the first time.
Normal looking guns with extraordinary roles in history.
At Rock Island Auction Company, we understand that every item that passes through our doors carries with it a story as unique and special as the item itself. That is why we find it essential to understand the legacy and history that surround some of these men and figures of the prohibition era. Their lives, while controversial, violent, and disturbing, gave rise to some of the most notable policy changes and reforms of the 20thcentury. The national interest and attention seen by some of these gangs shown a powerful light on the prevalence of crime leading to the allocation of additional resources needed for local law agencies to effectively pursue criminals.
Join us for our upcoming Premier Auction to see exceptional items and exquisite weaponry from across history. Lots from Pretty Boy Floyd, attributed pistols to Al Capone, and similar machine guns similar to those used with great success by the Dillinger Gang will be feature along with much, much more. We can’t wait to see you there.
Following his stinging defeat in the 1912 election, President Theodore Roosevelt planned a trip to South America with a lecture tour and river
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