This study examines the life of Revolutionary War soldier, Deborah Sam(p)son Gannett and how historians and theorists have analyzed her. It contains a deep look into theory and argues that Gannett should be considered a cross-dresser, due to an explanation of cross-dressing theory, gender theory, an introduction into women and war, virtue, and a brief look at how the work of her original biographer, Herman Mann, who wrote both her "biography" and some of the speeches she delivered to audiences during the Early American Republic, helped shaped popular assumptions of Gannett today.