This chapter traces Sylvester Manor's history, revealing a complicated social setting that runs counter to traditional stories of colonial life. Drawing on Sylvester Manor's own archive, the colonial documents of the region, and the ethnohistory and archaeology of early colonial Indian history, the chapter examines the contexts of Sylvester Manor's early plantation and its slaveholding. In particular, it considers Nathaniel Sylvester's employment of enslaved Africans and how he was able to consolidate his independent ownership of Shelter Island. It first explores Native histories prior to European colonization before discussing the relationships and interactions of European colonists and Native Americans in southern New England and coastal New York. Finally, it analyzes the role of social structures in the ability of English and Dutch to establish and expand colonial settlements, along with the host of actors and interests at stake within both the European and indigenous communities as well as these communities' notions of political authority and control, community networks, property, and personhood.
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