July 2, 1903 - Jack McGurn
McGurn built his reputation within the Chicago Outfit through a combination of personal vendettas and professional violence, becoming one of Capone's most trusted and frequently deployed enforcers during the height of Prohibition-era gang warfare. His career traced an arc from street-level retaliation to high-profile assassinations, placing him at or near some of the period's most consequential criminal events. The same notoriety that made him valuable to Capone ultimately marginalized him within the organization, leaving him to spend his later years on the periphery of a world that had moved on without him.
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