"Illuminating Strange Defeat and Pyrrhic Victory: The Historian Robert A. Doughty" is the first of a new genre of Journal of Military History articles designed to explore particular historiographical areas by focusing on the contributions of their most distinguished historians. In surveying the scholarship of Brigadier General (Rtd.) Robert A. Doughty as well as his role in shaping the History Department at the United States Military Academy, this article explores the evolution of English-language interpretations of the fall of France in 1940 and the French effort in the Great War while highlighting Doughty's efforts to teach the U.S. Army how to harness historical study in the interest of doctrinal development.