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This article uses evidence from the English High Court of Admiralty to examine the problem of mutiny and indiscipline among seafarers in the transatlantic trades during the 1680s and 1690s. It focuses on a venture of 1688, which is of particular interest not only for the light it sheds on maritime conditions, but also because it involved Daniel Defoe, a young and ambitious trader who was trying to establish a commercial opening in Chesapeake Bay. The article contextualizes this previously unknown venture, relating it to the development of the tobacco trade and its dependence on an expanding market and widening patterns of consumption. The failure of the voyage, in association with other business problems, had serious consequences for Defoe, leading to bankruptcy in 1692 and his withdrawal from direct involvement in overseas trade. Against a broader background of other voyages, the legal testimony heard by the court draws attention to the wider problem of mutinous conduct at sea. These cases were provoked by a range of grievances including pay, labour conditions and discipline. Repeatedly they raise questions about the conduct of masters at sea, including their rights and responsibilities. At the same time, the article argues that the upsurge in mutiny and indiscipline at sea, while revealing the inexorable tension between pay and productivity, also exposed deeper issues regarding seafaring custom and contract.