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This article studies the known studio portraits of William King (1768-1852), first governor of Maine, finding that the leader’s personal life and professional travels led to sittings with such noted master painters as Gilbert Stuart, Edward Greene Malbone, and Chester Harding. These living portraits reflect period styles, while later likenesses require a broad understanding of formal state portraiture and its historical elements. One portrait, having resurfaced recently, was found to have hung in the Hall of Flags in the State Capitol for almost thirty years; others required considerable research to determine their provenance. The Honorable James G. Blaine played an unexpected role in this history of King’s likenesses, while the author traces other portrait provenances through museum, probate, church, and vital records; deeds; family and town histories; and the papers of notable politicians like Rufus King of New York. The William King letters at MHS (Maine Historical Society) provide insight into family relations helpful in tracking down ownership trajectories. Deanna S. Bonner-Ganter earned an M.S. in Archives Management at Simmons College; an M.A. in Printmaking at Rutgers University; and a B.F.A. in Art Education at the College of Visual Arts, Boston University. She is Curator of Photography, Art, and Archives at the Maine State Museum.