The Underworld Podcast

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

April 7, 2026·52 min
Episode Description from the Publisher

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

AI Summary coming soon

Sign up to get notified when the full AI-powered summary is ready.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.

Listen to This Episode

Get summaries like this every morning.

Free AI-powered recaps of The Underworld Podcast and your other favorite podcasts, delivered to your inbox.

Get Free Summaries →

Free forever for up to 3 podcasts. No credit card required.