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| Cast | + Add Cast | 
| 18 cast members | 
| Name | Known for | 
|---|---|
| Kevin Weeks
 
Self - Ex-Bulger Lieutenant
 | |
| Howie Carr
 
Self - Boston Radio Broadcaster
 | |
| Pat Nee
 
Self - Ex-Bulger Enemy
 | |
| Howie Winter
 
Self - Ex-Winter Hill Gang Boss
 | |
| Michael Sullivan
 
Self - Boston U.S. Attorney
 | |
| Tom Foley
 
Self - Ex-Massachusetts State Police
 | |
| Bob Fitzpatrick
 
Self - Ex-Boston FBI (as Robert Fitzpatrick)
 | |
| David Jeremiah
 
Narrator (voice)
 | |
| Gennaro Angiulo
 
Self - New England Mafia Underboss (archive footage)
 | |
| James 'Whitey' Bulger
 
Self - Winter Hill Gang Boss (archive footage)
 | |
| William Bulger
 
Self - United States Senator, Massachusetts (archive footage)
 | |
| John Connolly
 
Self - FBI Agent (archive footage)
 | |
| Stephen Flemmi
 
Self - Winter Hill Gang Member (archive footage)
 | |
| Brian Halloran
 
Self - Winter Hill Gang Member (archive footage)
 | |
| John McIntyre
 
Self - DEA Informant (archive footage)
 | |
| John Morris
 
Self - FBI Agent (archive footage)
 | |
| Raymond Patriarca
 
Self - New England Mafia Boss (archive footage)
 | |
| Ilario Zannino
 
Self - New England Mafia Consigliere (archive footage)
 |