Bootlegging/ˈbuːtleɡɪŋ/ Definition 1 of 3Pro Tip 1/3Historical significance Understanding Prohibition helps grasp why 'bootlegging' often implies alcohol. History classes cover bootlegging's role during Prohibition. Pro Tip 2/3Crime connotation 'Bootlegging' conveys a sense of illegality beyond just alcohol. Bootlegging designer bags can lead to arrest. Pro Tip 3/3Not just selling The term also includes making and distributing illegal goods. He ran a bootlegging operation, creating fake merchandise.