John “Red” Hamilton – Dillinger Associate

John "Red" Hamilton

John “Red” Hamilton

John “Red” Hamilton, aka Three Finger Jack, was a gangster and associate of John Dillinger and Pretty Boy Floyd who was active in the mid-20th century.

Hamilton was born in 1899 in Canada to an Irish-Canadian father from Ontario and a German-American woman from New York. As a child, he lost two fingers on his right hand somewhere along the line, earning him the moniker “Three Finger Jack.” He was arrested in 1927 for robbery and sent to prison in Michigan City, where he became friends with John Dillinger and Harry “Pete” Pierpont.

Using guns smuggled in by Dillinger, Hamilton, Pierpoint, and others, escaped from the prison on September 26, 1933, and quickly formed the Dillinger Gang, which robbed banks all over the Midwest. While hiding out with the gang in Chicago, Illinois, Hamilton was caught in a garage by Chicago police sergeant William Shanley. Hamilton shot the officer, causing the whole Dillinger Gang to flee to Florida.

A month later, Hamilton, Dillinger, and Pierpont robbed the East Chicago, Indiana bank and killed a police officer in their getaway. Most of the gang then fled to Arizona, where a number of them, including John Dillinger, were captured, but Hamilton did not accompany them. After being extradited to Indiana, Dillinger escaped from the Crown Point Jail in March 1934, and Hamilton quickly hooked back up with him.

Dillinger and his gang hid out at Little Bohemia, Manitowish Waters, Wisconsin. An all-out gun battle occurred here in which two men were killed and four wounded as the gang made their escape.

Dillinger and his gang hid at Little Bohemia, Manitowish Waters, Wisconsin. There was an all-out gun battle in which two men were killed, and four wounded as the gang escaped.

Along with Homer Van Meter, Baby Face Nelson, and others, they began to rob banks again. After a furious gun battle with the FBI at Rhinelander, Wisconsin’s Little Bohemia Lodge, on April 22, 1934, the gang split up. Nelson headed to Michigan’s Upper Peninsula, while Hamilton, Dillinger, and Van Meter fled to Hastings, Minnesota. There, lawmen ambushed them, and Hamilton sustained a mortal wound in the back. The gang then fled to Chicago and soon holed up at a hideout of the Barker-Karpis Gang in Aurora, Illinois. Hamilton eventually died in the last days of April. The men then buried his remains in a gravel pit near Oswego. Later, in August 1935, the remains were dug up and identified by dental records, and Hamilton was interred in an unmarked grave in the Oswego Township Cemetery.


© Kathy Alexander/Legends of America, updated November 2022.