John “Red” Hamilton – Dillinger Associate
The roaring twenties and the desperate thirties in America were marked by economic hardship and, paradoxically, a surge in organized crime. Among the notorious figures who rose to infamy during this era was John “Red” Hamilton, a name often whispered alongside those of John Dillinger and Pretty Boy Floyd. His life, a tapestry woven with threads of robbery, prison breaks, and violent encounters, paints a vivid picture of the lawless landscape of the American Midwest. John “Red” Hamilton was more than just another gangster; he was a key player in one of the most audacious crime sprees in American history.
Born in 1899 in Canada, Hamilton’s heritage was a blend of Irish and German roots, his father hailing from Ontario and his mother from New York. Early in life, an accident resulted in the loss of two fingers on his right hand, a distinguishing feature that earned him the grim nickname “Three Finger Jack.” This physical characteristic would become a lasting identifier in the criminal underworld and in the files of law enforcement agencies. The early life of John “Red” Hamilton was shrouded in mystery, with only glimpses available through historical records and anecdotal accounts.
Hamilton’s descent into crime culminated in his 1927 arrest for robbery. He was subsequently sentenced to prison in Michigan City, Indiana. This incarceration proved to be a pivotal moment in his life, for it was within the prison walls that he forged alliances with two other men who would become notorious figures in their own right: John Dillinger and Harry “Pete” Pierpont. These three men, bound by a shared disdain for authority and a thirst for wealth, laid the foundation for what would become the infamous Dillinger Gang. The prison environment served as a breeding ground for their criminal ambitions, solidifying their bond and setting the stage for their future exploits. The association of John “Red” Hamilton with such notorious criminals cemented his place in the annals of American crime history.
In a daring act of defiance, Hamilton, Pierpont, and others, emboldened by guns smuggled into the prison, orchestrated a brazen escape on September 26, 1933. This escape marked the official formation of the Dillinger Gang, a group that would soon terrorize banks across the Midwest. Their tactics were bold and ruthless, their heists meticulously planned and executed with a chilling efficiency. The Dillinger Gang quickly became a symbol of lawlessness, capturing the attention of the nation and sparking a relentless pursuit by law enforcement. John “Red” Hamilton, as a key member, was instrumental in the gang’s success and notoriety.
While seeking refuge with the gang in Chicago, Illinois, Hamilton’s luck ran thin. He was apprehended in a garage by Chicago police sergeant William Shanley. In a desperate attempt to evade capture, Hamilton shot the officer, an act that forced the entire Dillinger Gang to flee the city and seek refuge in Florida. This incident underscored the gang’s willingness to resort to violence and solidified their reputation as dangerous criminals. The shooting also intensified the pressure on law enforcement to bring them to justice.
The gang’s criminal activities continued unabated. A month later, Hamilton, Dillinger, and Pierpont robbed a bank in East Chicago, Indiana, and during their escape, they killed a police officer. This brazen act of violence further fueled the public’s outrage and intensified the manhunt. Realizing the heat was on, the majority of the gang fled to Arizona in an attempt to evade capture. However, Hamilton did not accompany them.
In Arizona, Dillinger and several other members of the gang were eventually captured. Dillinger was extradited to Indiana, but his incarceration was short-lived. In March 1934, he orchestrated another daring escape, this time from the Crown Point Jail. Upon his escape, Dillinger wasted no time in reconnecting with Hamilton, and the two men resumed their criminal partnership.
The reunited Dillinger Gang, now including Homer Van Meter, Baby Face Nelson, and others, embarked on another wave of bank robberies. Their actions were met with increasing resistance from law enforcement, culminating in a furious gun battle with the FBI at the Little Bohemia Lodge in Rhinelander, Wisconsin, on April 22, 1934. The shootout resulted in casualties on both sides, forcing the gang to scatter.
Following the Little Bohemia shootout, Nelson fled to Michigan’s Upper Peninsula, while Hamilton, Dillinger, and Van Meter sought refuge in Hastings, Minnesota. However, their respite was brief. Law enforcement ambushed them, and Hamilton sustained a mortal wound to the back. Despite the severity of his injury, the gang managed to escape, fleeing to Chicago and eventually seeking refuge in a hideout belonging to the Barker-Karpis Gang in Aurora, Illinois.
Despite the gang’s efforts to care for him, Hamilton’s wound proved fatal. He succumbed to his injuries in the final days of April. The remaining members of the gang, desperate to conceal his death, buried his body in a gravel pit near Oswego, Illinois. His final resting place remained a secret for over a year.
In August 1935, authorities acting on information, exhumed the remains from the gravel pit. Dental records were used to positively identify the body as that of John “Red” Hamilton. Following the identification, Hamilton was interred in an unmarked grave in the Oswego Township Cemetery, a final, anonymous resting place for a man who had lived a life of crime and violence.
The life and death of John “Red” Hamilton offer a glimpse into the turbulent era of the Great Depression and the rise of organized crime. His association with John Dillinger and other notorious figures solidified his place in the annals of American criminal history. Though his life was cut short by violence, his story continues to fascinate and intrigue, serving as a reminder of the lawlessness that once gripped the American Midwest. The story of John “Red” Hamilton is a testament to the dark side of the American dream, a cautionary tale of ambition gone astray.