← Gangland Chronicles · Season 1

The Winter Hill Gang

S1 · E6 · 02 Sep 2024 · 22 min

Whitey Bulger's notoriously violent and untouchable Winter Hill Gang are the kings of Boston's underworld, until a secret alliance comes to light.

Guest Stars (13)

Sami Jarroush as Self - Historian

Tom Foley as Self - Colonel & Superintendent (Ret.), Massachusetts State Police

Emily Sweeney as Self - Boston Globe Journalist / Author, 'Gangland Boston'

Phyllis Karas as Self - Adjunct Professor, BU School of Journalism / Co-Author, 'Brutal'

Geoff Schumacher as Self - VP of Exhibits & Programs, The Mob Museum

James 'Whitey' Bulger as Self - Boss of the Winter Hill Gang (archive footage)

Howie Winter as Self - Boss of the Winter Hill Gang (archive footage)

Stephen Flemmi as Self - Lieutenant in the Winter Hill Gang (archive footage)

Kevin Weeks as Self - Lieutenant in the Winter Hill Gang (archive footage)

Frankie Angiulo as Self - New England Mafia (archive footage)

Gennaro Angiulo as Self - New England Mafia (archive footage)

John Connolly as Self - FBI Agent (archive footage)

John McIntyre as Self - FBI Informant (archive footage)