In 1800, Gilbert Stuart began three paintings of his friend, republican writer, Sarah Wentworth Apthorp Morton--the Worcester, Winterthur, and Boston portraits. While Morton has been remembered more for a tragic personal family scandal than for her literary endeavors, Stuart's provocative images acknowledged her as both a poet and an intellect. His portraits presented a progressive and potentially controversial interpretation of his sitter--the lovely and learned Morton--by prioritizing the writer's life of the mind rather than her socially prescribed life in the world. This study reconstructs the circumstances by which Stuart composed the group of Morton paintings that culminate in his unorthodox Worcester rendering through which he ultimately depicted Morton as the first woman of ideas in American art. Supported by close readings of her work, this dissertation illuminates both the course and depth of the exceptional personal and professional relationship between Morton and Stuart. The paths of the two republican figures crossed at several historic junctures and is highlighted by the interconnectivity of their work. Most significantly, the Stuart portraits represent an ideal lens through which to view Morton's life and work as well as to follow the Boston native's transformation into one of America's earliest women of ideas. / text