Operation Rolling Thunder was a United States led operation, with the political aims of interdicting and preventing the North Vietnamese support of the South Vietnam rebellion, during the later stage of the Vietnam war. Despite being a superpower, Operation Rolling Thunder failed, and the USA lost the war. In this essay, the air power theorists John A. Warden and Robert A. Pape, and their theories regarding how air power should be used to reach success, are used to analyze this failure. The use of these theories in a parallel manner enables to comprehend empirical sources and in turn recognize anomalies in the decision making and missteps of the American leadership. By keeping the case of Rolling Thunder in focus and thereby try and understand what happened, the aim is to create an understanding for why the potent power of the US Air Force made an inadvertent turn despite exercising air superiority throughout most of the operation. This examination concludes that there were three deciding factors in the American failure, which are: (i) absence of efficient attacks against the North Vietnamese leadership, (ii) lack of correlation between strategy and political aim, (iii) lack of experience and communication within the American leadership.