Karen Ordahl Kupperman's scholarship focuses on the Atlantic world in the sixteenth and seventeenth centuries. Her current project is on language as a source of power in early English colonization. Her recent publications include Pocahontas and the English Boys: Caught between Cultures in Early Virginia (2019) and an edition of Henry Spelman's Relation of Virginia (2019) from the original manuscript. She has also published The Atlantic in World History (2012), an edition of Richard Ligon's True and Exact History of the Island of Barbados (2011). Among her earlier works, Indians and English: Facing Off in Early America (2000) won the American Historical Association's Prize in Atlantic History and Providence Island, 1630-1641: The Other Puritan Colony (1993) won the American Historical Association's Albert J. Beveridge Award.
Kupperman explores the intertwined lives of Pocahontas and three English boys, Thomas Savage, Henry Spelman, and Robert Poole, who were sent by Jamestown's leaders to live among the Chesapeake Algonquians. All were in their early teen years when they first met; Pocahontas was the youngest. Because of their knowledge of both English and Indian cultures, they were arguably the most important people in early Virginia, but their true loyalties were always suspect.