| Stephen Rakes |
Himself - Bulger Extortion Victim |
| James 'Whitey' Bulger |
Himself - Defendant |
| Tommy Donahue |
Himself - Son of Victim Michael Donahue |
| David Boeri |
Himself - WBUR Senior Reporter |
| Steve Davis |
Himself - Brother of Victim Debra Davis |
| Dick Lehr |
Himself - Author / Journalist |
| Shelley Murphy |
Herself - Boston Globe Reporter |
| Patricia Donahue |
Herself - Wife of Victim Michael Donahue |
| J.W. Carney Jr. |
Himself - Bulger Defense Attorney (voice) |
| Kevin Cullen |
Himself - Boston Globe Coulmnist |
| Kevin Weeks |
Himself - Former Member, Winter Hill Gang |
| Bob Long |
Himself - Det. Liut. Inspector, Massachusetts State Police, Retired |
| T.J. English |
Himself - Author / Journalist |
| Daryl Zules |
Himself - Bulger Defense Team |
| Angela Clemente |
Herself - Forensic Intelligence Analyst |
| Bob Fitzpatrick |
Himself - Former FBI Assistant Special Agent in Charge (ASAC) |
| Zachary R. Hafer |
Himself - Asst. United States Attorney, Bulger Prosecutor |
| Maryann Davis |
Herself - Wife of Steve Davis |
| David Wheeler |
Himself - Son of Victim Roger Wheeler |
| Edward T. Hinchry |
Himself - Donahue Family Attorney |
| Tom Foley |
Himself - Superintendent, Massachusetts State Police, Retired |
| James E. McDonald |
Himself - John Connolly Defense Attorney |
| David Frank |
Himself - Managing Editor, Massachusetts Lawyer's Weekly |
| Jonathan Hall |
Himself - WHDH Boston Reporter |
| Hank Brennan |
Himself (voice) |
| Brian T. Kelly |
Himself (voice) |
| Fred M. Wyshak Jr. |
Himself (voice) |
| Anthony DeFabrizio |
Hank Brennan (voice) |
| Louis Cogliano |
John Martorano (voice) |
| John Greene |
Stephen Flemmi (voice) |
| Vito Amorelli |
John Morris (voice) |
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