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The Winter Hill Gang: Blood, Betrayal & The Silence of Somerville | The Missing Files
In this episode of The Missing Files, host Madison Rogers delves into the brutal history of the Winter Hill Gang, a powerful Irish-American criminal organization that dominated Somerville and Boston in the mid-20th century. This true crime deep dive explores how James 'Buddy' McLean and Howard 'Howie' Winter built their empire through trucking fronts, loan sharking, and ruthless intimidation, transforming a neighborhood dispute into a bloody turf war against the rival McLaughlin Gang. Listeners will uncover the specific mechanics of their rise, from leveraging gambling proceeds to weaponizing…
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