Boston's Irish Mob Gang War: The Winter Hill Gang
The Underworld Podcast
The Underworld Podcast
4.7 • 1K Ratings
🗓️ 7 April 2026
⏱️ 50 minutes
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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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