To what extent does educational gaming add value to more traditional instructional models in learning core concepts of national security and warfighting? This paper presents the results from a quasi-experimental, cross-sectional, and longitudinal study of students taking two standardized courses in the Joint Military Operations department at the US Naval War College. Split into wargaming and non-wargaming sections by instructor preference, subject learning is measured through self-reported and objective measures at three points: prior to the start of the content block on “Operational Art”; after the case study of the WW2 battle of Leyte Gulf but prior to any wargaming; and for subjects in wargaming course sections, after participating in the Leyte Gulf scenario of the “War at Sea” wargame. The results support the hypotheses that wargaming increases learning and alter student preferences in favor of learning through gaming but fail to find evidence that students recognize the value of the debriefing phase of educational gaming. This article adds to existing studies by focusing on an understudied practitioner population—graduate-level career military officers at a professional military education (PME) institution—and mitigating several of the methodological challenges facing many scholarly projects in the study of educational gaming in political science.