Cousin Harry Pierpont (1902-1934), later famous as the trigger man for the Dillinger gang, started his criminal career shortly after being struck on the head and suffering an injury. This is the earliest mention I've found of his criminal career. I found this through the Depauw University archives.
Black Sheep Sunday – create a post with the main focus being an ancestor with a “shaded past.” Bring out your ne’er-do-wells, your cads, your black widows, your horse thieves and tell their stories. And don’t forget to check out the International Black Sheep Society of Genealogists (IBSSG). This is an ongoing series at GeneaBloggers.