James Joseph "Whitey" Bulger

James Joseph "Whitey" Bulger was an Irish American mob boss who befriended Randy when he was being transferred from Los Angeles to Boston when he was being processed in Oklahoma City, James reunites with Randy in Oklahoma City again before he was killed in a Federal Prison in Hazelton West Virginia less than 1 day as he entered the facility.

Appearances:

In "much stranger things than usual" Matt states that on his way to Oklahoma City on a road trip Matt goes up to a buffalo in Wyoming, referencing to the time being when Matt and his family were visiting Randy to see how he's living, that same trip Matt did meet James at the FTC before going to Boston for court appearance.

In the episode "things can't get weirder" James who is in a wheelchair arrives at Oklahoma City for transferring to Hazelton, Randy met him at the jetway at the FTC and escorted him to his cell and they were catching up on how things were going, Randy learns that while in Florida (USP Coleman) that he's gone soft, and became less of a monster than he was in the 70s.

In the episode "danger is close" Matt and Randy go to his funeral in Boston, making it Matt's first time going to Boston.