Who was the greatest of the bank and train robbers? Dan Clutter Denison, Iowa I would have to go with Indian Territory outlaw Henry Starr, a three-eighths Cherokee. He allegedly robbed 21 banks in a nearly 30-year career (minus jail time). His first job was a train depot holdup in 1892, after which he cold-bloodedly killed a deputy U.S. marshal. His gang went on a rampage, robbing two banks and a train in a three-month period. Starr was captured in Colorado and sent back to Fort Smith,


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