Whitey Bulger was involved in numerous significant deals and criminal enterprises throughout his career. His criminal activities included extortion, drug trafficking, racketeering, and more, solidifying his status as a formidable and dangerous figure in the Boston crime world. Under his leadership, the Winter Hill Gang became a dominant force in the city’s criminal underworld, engaging in various illegal activities while maintaining a tight grip on their territory. Bulger’s notoriety and influence extended beyond Boston, earning him a place among the most legendary crime bosses in American history.