John Dillinger was paroled on May 10, 1933, after his father campaigned for his release. Just over a month later, on June 21, he robbed his first bank, stealing $10,000 from the New Carlisle National Bank. By August, he had hit another bank in Bluffton, Ohio, and was arrested in Dayton before being transferred to the Allen County Jail in Lima to face charges. It was there that a group of criminals, including Charles Makley, Harry Pierpont, Russell Clark, and Ed Shouse, arrived to break him out.
Among them was John “Red” Hamilton, a Canadian-born bank robber whose life had been shaped by a childhood dare that cost him two fingers. Hamilton was born on August 27, 1899, in Inlet, Ontario, Canada, to an Irish-Canadian father and a German-American mother. His family moved to Sault Ste. Marie, Michigan, when he was three.
As a boy, he accepted a dare to touch the spinning wheel of a passing train while sledding near the railroad tracks. The stunt cost him the index and middle fingers on his right hand and earned him the nickname “Three-Finger Jack. ”
He left school in the tenth grade and worked as a lumberjack and as a deckhand on a freighter on the Great Lakes. In 1919, he and two friends worked for the Oakland Motor Company in Pontiac, Michigan.
By 1921, he was back in Sault Ste. Marie, where he married Mary Stevenson. Farming could not support his wife and their two sons, Howard and Orville, so Hamilton turned to bootlegging on the side. His criminal career became full-time when his illegal brewing still was discovered in the family’s chicken coop.
He jumped bail in 1924 and joined the gang of his wife’s brother, Alvia. On January 3, 1927, Hamilton, Raymond Lawrence, Clayton Powers, Curtis Turner, and Mary’s brothers robbed the Leki Foundry in Muskegon Heights, taking $33,000. Later that same year, a group including Hamilton and Lawrence stole more than $25,000 from the Kent State Bank in Grand Rapids. Hamilton and Lawrence then planned to rob a bank in South Bend, Indiana, but called it off after a hostage escaped and contacted authorities.
When local police chief James Head investigated a report of a man putting Wisconsin license plates on a Michigan car, both men were arrested. Hamilton was transferred to the Indiana State Prison in Michigan City to serve a 25-year sentence. His wife divorced him and remarried, but she died in childbirth in 1930. Despite his good behavior, Hamilton’s clemency requests were denied year after year.
The parole board considered him dangerous. In prison, he joined a group of felons who gathered daily to discuss strong-arm experiences, bank-robbing techniques, and escape plans. The group included Harry Pierpont, Russell Clark, and Charles Makley. In 1929, Hamilton helped educate a recent transfer from Pendleton Reformatory—a 26-year-old serving time for a bungled robbery of an Indiana grocer.
That young man was John Herbert Dillinger. After Dillinger was paroled in May 1933, he returned the favor. He smuggled three guns into the prison inside a 200-pound box of thread from the Gordon Shirt Company, marked with a red X. On the afternoon of September 26, 1933, ten men walked out of the prison, taking guards hostage as they headed for the front gate.
The gang soon learned that Dillinger had been arrested in Ohio for bank robbery and was being held at the Allen County Jail in Lima. To fund an escape and free Dillinger, the gang robbed the First National Bank of Saint Mary’s, Ohio, on October 3, 1933, making off with $14,000. Nine days later, Hamilton accompanied Makley, Pierpont, Clark, and Shouse to the Lima jail and broke Dillinger out. Hamilton never entered the building and did not take part in the killing of Allen County Sheriff Jeff Sarber.
On December 13, 1933, Hamilton and the Dillinger gang raided a Chicago bank and emptied its safe deposit boxes, netting as much as $50,000. On January 15, 1934, Hamilton and Dillinger robbed the First National Bank in East Chicago, Indiana, taking $20,376. During the heist, police officer William O’Malley was killed. It was the only time Dillinger was ever charged with homicide.
By the end of the year, Hamilton had risen to third place on Indiana’s list of Public Enemies, behind Dillinger and Pierpont. After being shot twice during the East Chicago robbery, Hamilton was left in the care of his girlfriend, Pat Cherrington, and an underworld physician named Joseph Moran, while Dillinger and the others headed to Tucson, where they were briefly apprehended. Hamilton then topped the Public Enemies list until Dillinger escaped from Crown Point and formed a new gang with Hamilton, Homer Van Meter, Tommy Carroll, Eddie Green, and Baby Face Nelson. The gang carried out a series of lucrative but chaotic armed robberies.
On one occasion, Hamilton was shot in the shoulder by an elderly judge across the street, who also wounded Dillinger. Facing a massive manhunt and intense media coverage, Hamilton and Dillinger paid a discreet visit to Hamilton’s sister’s home in Sault Ste. Marie, Michigan, on April 17, 1934. It would be Hamilton’s final meeting with his sister.
The gang retreated to the Little Bohemia Resort after returning to Chicago. On April 22, FBI agents led by Melvin Purvis raided the resort after receiving a tip. The raid went badly from the start: agents opened fire on a car carrying three local work camp employees by mistake, while Dillinger, Hamilton, Van Meter, and Carroll slipped out the back door. The following day, Hamilton, Dillinger, and Van Meter were confronted by authorities in Hastings, Minnesota, and another shootout broke out.
Hamilton was mortally wounded while escaping in a car with the rest of the gang. The gang took him to see Dr. Joseph Moran in Chicago, but the doctor refused to treat him. Hamilton died on April 26, 1934.
Dillinger laid his friend to rest near Oswego, Illinois.