The Winter Hill Gang
Was the Winter Hill the most notorious Boston crime syndicate?
4.1 (19)
55 mins
Discover the rise of the Winter Hill Gang that dominated the city's underworld for decades. Explore its violent power struggles, secret alliances, and the criminals who built one of America's most feared gangs.
Ep 1:
The Man in the Bathrobe
A fugitive killer's calm arrest in Florida opens the door to Boston's bloodiest secret: a gang war-torn city, a corrupt bargain, and the rat nobody suspected.
Ep 2:
The Executioner's Education
A half-Italian, half-Irish outsider becomes Winter Hill's most trusted killer, while Howie Winter builds an underworld empire that a savage rival war threatens to unravel.
Ep 3:
The FBI's Rat and the Race Fix
An FBI informant deal turns Whitey Bulger into an untouchable operator, as a rigged horse-racing scheme collapses and a Tulsa businessman becomes an unlikely target.
Ep 4:
Blood in Tulsa
A country club murder in Oklahoma sets off a deadly chain reaction, exposing just how far corrupt agents will go to protect their prized informant.
Ep 5:
The Steak Dinner Confession
A steak dinner and a stack of court papers shatter Johnny Martorano's loyalty, triggering a cooperation that brings down killers, cops, and an entire criminal order.
Ep 6:
Sixteen Years in Plain Sight
Whitey Bulger vanishes for sixteen years, hiding in plain sight with stashed cash and stretched socks—until one overlooked detail finally betrays him.
Ep 7:
The Bargain Boston Made
As the last players fade into quiet lives or violent ends, Boston reckons with the true cost of a government's decades-long bargain with murder.
Discussions (5)
Carson
Level 7 · 2 mo agoMartorano had dinner with the Black Mass producers after killing 20 people and doing 12 years. Only in Boston.
Adam
Level 3 · 2 mo agoThe Deegan case broke me. Four innocent men rotting in prison for decades while the FBI KNEW. That's not a few bad apples, that's the whole barrel rotten from the top.
Lincoln
Level 3 · 2 mo agoMartorano had dinner with the Black Mass producers AND sold his story? Dude killed 20 people, did 12 years, and came out with a book deal. Only in Boston.
