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This article considers how enslaved pilots used the coastal waters of the Anglophone-Americas during the Revolutionary Era as a cultural and political space to invert racial/social valuations and gain uncommon privileges. It examines how captives in discrete societies similarly exchanged environmental and nautical wisdom for lives of privileged exploitation. Most were owned by slaveholding-merchants, who dispatched several pilots in pilot boats to navigate vessels into port. Recognizing their inability to supervise pilots who remained aboard ship for days, sometimes weeks, and return home in pilot boats capable of carrying them beyond their grasp, slaveholders granted these trusted men considerable autonomy and geographic mobility, permitting them to cultivate semi-independent, wage-earning lives that allowed some to obtain freedom. Water was an integral element in pilots’ lives. Waterways are often treated as literary backdrops; not regions for cultural creation. Coastal waters afforded pilots with liminality between the regimes of terrestrial and maritime authority, providing shipboard privileges exceeding those received by bondpeople toiling in other capacities. Enslaved pilots became temporary ship captains, permitting them to curse and command white sailors and officers, toast white women, and assault white shipmasters even as their race and status sought to subjugate them. The Revolutionary Period enhanced pilots’ opportunities, enabling them to manipulate revolutionary rhetoric, wartime circumstances, and rapidly changing social dynamics to subvert white authority, appropriate privileges, and seize freedom and sometimes rights for themselves and their family members.