When Prohibition swept across America in 1920, promising sobriety and morality, few anticipated the explosive rise of an underground economy fueled by alcohol. Rather than drying out the nation, the constitutional ban on liquor sparked widespread defiance, turning ordinary citizens into outlaws overnight. Bootleggers, once mere backwoods distillers and small-time hustlers, quickly seized opportunity in the face of restriction. By supplying forbidden spirits through secret networks and speakeasies, these outlaw entrepreneurs amassed immense wealth and influence, leaving an indelible mark on American history. This article explores how bootleggers transformed prohibition from a legislative ideal into a lucrative black market empire.