He is known to have been born in Missouri but raised in Sullivan, Indiana, and was a cowboy at one time, as well as having ridden in horse races for money.

Joe Pierce was killed in a tragic mining accident while still a youth, and Willis who was learning the trade with Charley and was part of the Dalton gang for a time.

Pierce is known to have taken part in numerous bank and train robberies, and was present at the Battle of Ingalls, a gunfight between the gang and US Marshals which left three Deputy Marshals dead, two civilians dead, one gang member captured and two (including Pierce) wounded.

During the Ingalls gunfight, "Bittercreek" Newcomb and Charley Pierce were wounded, and "Arkansas Tom" Jones was captured.

Pierce had known Newcomb longer than any other member of the gang, having met him while working as a ranch hand on the Tulsa Stockyard Railhead.