Twenty-five hundred years ago, Sun Tzu articulated his views about how best to wage war. On November 28, 1984, Caspar Weinberger, then secretary of defense in the United States, pronounced his own doctrine for waging war. These two doctrines, separated by two and a half millennia, one prepared for a leader in a monarchy, the other for a leader in a democracy, express significantly different views about when and how to fight a war. Seemingly contradictory though these perspectives appear to be, they also seem to be reconcilable by the selectorate theory of war, a theory that focuses on policy choices and resource allocations that are incentive compatible for a leader who hopes to survive in office.(1) Thus, when leaders depend on support from a small coalition of essential backers to stay in office-as is true in monarchy, junta, and autocracy-then it is incentive compatible for them to follow the advice given by Sun Tzu. By contrast, when leaders depend on support from a large coalition, then they are expected to follow the recommendations of Caspar Weinberger. We summarize the relevant elements of the selectorate theory and then show how it relates both to claims by Sun Tzu and Caspar Weinberger and to the known regularities associated with the so-called democratic peace. For instance, the theory explains why democracies are unlikely to fight wars with each other but do fight with nondemocratic states and why they typically win. The selectorate theory, as applied to war, was constructed with those regularities in mind. Therefore, a demanding test requires an examination of novel hypotheses that follow from that theory. In this article we develop measurement procedures and conduct empirical tests of five novel hypotheses derived from the selectorate theory of war.