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The enslavement of Indians by Englishmen in seventeenth-century America is often characterized by historians as an inconsequential phenomenon that either presaged the large scale enslavement of African peoples or, conversely, resulted from the expansion of the plantation complex. The early enslavement of Indians, however, was neither closely related to emerging labor demands nor an accident of Anglo-American colonialism. Indian slavery was purposeful and rationalized, often, by pointing to the need to punish natives for their crimes and by emphasizing that bondage might serve to rehabilitate recalcitrant individuals. Eventually, the enslavement of Indians would be almost indistinguishable from the enslavement of Africans, but throughout much of the seventeenth century Indian slavery was a distinct practice. African slavery was accepted, in part, because the English viewed them as fundamentally different. Indian slavery was accepted, paradoxically, because the English allowed that the indigenous inhabitants of North America were not unlike themselves. Indian slavery was premised on social and cultural assumptions that appear contradictory in retrospect. Yet, by retelling the story of Indian slavery in the context of the early modern Atlantic world, including Anglo-Spanish relations, this essay reveals that human bondage was both more important to the English inhabitants of colonial America than is generally appreciated and more complicated than historians have admitted.