This study is a theoretical and historical exploration of the role and relevance of airpower in counterinsurgency (COIN). Despite an overwhelming material advantage in airpower and the popular belief that this provides America with an inherently beneficial warfighting asymmetry, the US struggles to realize the full value of airpower in COIN. The author proposes that airpower provides the US with a conditional advantage that must be deliberately unlocked through strategic deliberation. The author further proposes that a distinct theory of airpower for COIN is needed to foster and guide strategy formulation in order to optimize the application of airpower in this growing mission area. As a first step in developing this proposed theory, the author applies an existing airpower theory, Colonel John Warden s Enemy as a System, to three distinct historical cases in search of meaningful patterns.