The North Side Gang: Chicago’s Irish-American bootlegging powerhouse during Prohibition, rose from street gangs under charismatic leader Dean O’Banion and waged a brutal, multi-year war against Al Capone’s Chicago Outfit. Fueled by ethnic rivalries, territorial disputes, and high-stakes hijackings, the feud escalated through retaliatory ambushes, drive-by shootings, and bombings—culminating in the infamous St. Valentine’s Day Massacre of 1929, where seven of Bugs Moran’s men were executed in a garage. The slaughter shattered the North Side Gang, accelerated Capone’s downfall, and became a defining symbol of the violent chaos of the Roaring Twenties underworld.

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