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The Underworld Podcast

Boston's Irish Mob Gang War: The Winter Hill Gang

The Underworld Podcast

The Underworld Podcast

True Crime, Documentary, History, Society & Culture

4.71K Ratings

🗓️ 7 April 2026

⏱️ 50 minutes

🧾️ Download transcript

Summary

In 1960s Boston, Buddy McLean ignited a savage gang war after tensions with the McLaughlin brothers boiled over into open bloodshed. What started as neighborhood beef turned into a cycle of ambushes, barroom executions, and street hits that terrorized Boston. McLean’s Winter Hill crew proved more organized and ruthless, picking off rivals and seizing control as bodies piled up. By the end, the McLaughlins were shattered, and the war set the stage for the rise of Whitey Bulger and the modern Boston mob. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Welcome to the I Can't Sleep Podcast with Benjamin Boster.

0:08.0

If you're tired of sleepless nights, you'll love the I Can't Sleep podcast.

0:16.0

I help quiet your mind by reading random articles from across the web to bore you to sleep with my soothing voice.

0:24.6

Each episode provides enough interesting content to hold your attention, and then your mind lets you drift off.

0:34.6

Find it wherever you get your podcasts.

0:41.7

That's I Can't Sleep with Benjamin Boster.

0:53.5

June 7th, 1964, Boston, and the city is turning into a free-for-all for anyone who can get a crew together.

1:01.0

It's one of the few major cities in America where the Italian mafia isn't the dominant force, leaving room for others to apply their trade.

1:09.0

Two of the others are the McClauchland gang from Charlestown and the Winter Hill gang from Somerville.

1:15.0

Both are Irish, and they've been at war for the last few years.

1:19.2

What started out as a drunken fight during Labor Day weekend in 1961 over someone disrespecting a woman,

1:25.5

has turned into an all-out gang war in the city of Boston and the surrounding suburbs.

1:30.3

If you don't know Boston and have never seen an Affleck movie, Charlestown is a rough, working-class Irish neighborhood just north of Boston's downtown.

1:38.3

And Somerville is, or was, a rough working-class Irish neighborhood in the nearby suburbs. Think guys in fitted Red Sox hats

1:46.5

with terrible fades and super thin lion beards who love a good brawl. The Winter Hill gang,

1:52.4

later made infamous by Whitey Bulger, takes their name from the neighborhood of Winter Hill,

1:57.7

where they operate. They're led by a local street fighting legend by the name of James Buddy McLean.

2:04.2

The McClauchland gang is led by three brothers, Bernie, George, and Edward.

2:08.8

And in the summer of 1964, the momentum is on their side.

2:13.6

A month earlier, they had taken out a top Winter Hill member.

2:19.6

And now, they feel crazy enough to take another shot on McLean after several failed hits.

2:23.5

But getting him won't be easy.

...

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