Strategy and organization theory enjoy a reawakening interest in historical analysis. In this essay, we suggest that this engagement should include strategy’s linkage to the history of military strategy. We develop our argument through an exegesis of Carl von Clausewitz’ treatise On War. We claim that Clausewitz’ theorization of strategy advances the ongoing scholarly conversation on the practice of strategy in three specific ways. First, he defines a distinctive locus for the notion of strategy as the bridge between policy and tactics; in so doing, he addresses what has been criticized as strategy’s conceptual drift. Second, with Clausewitz, we can pose the question of strategy’s effectiveness in a critical, reflexive way. This opens up a way to answer the “so-what” question that has hampered strategy as practice research. Third, as an educator in military affairs of the Crown Prince, Clausewitz invites reflection on strategy’s pedagogy. Following Clausewitz, strategy may not want to concern itself with distilling the next practice from past history but immerse strategy students in great detail in history in order to develop their critical faculties.