Leonard Wood served as a Military Governor in Cuba from 1898 (Santiago) and 1899 to 1902, later as the Military Governor of the Moro Province in the Philippines from 1903 to 1906, and eventually as Governor General for the Philippines until his death in 1927. His military operations in support of American strategic aims provide lessons in both stability operations and civil military relations. Wood developed a detailed understanding of both theaters, and arranged his actions (both civil and military) in time, space, and purpose to accomplish American strategic aims. Leonard Wood conducted a variety of civil and military operations as the Military Governor of Cuba and the Military Governor of the Moro Provence in the Philippines. Critics generally praise his military governorship of Cuba, and condemn his military governorship of the Moro Province. The logic these critics use is that Wood was successful in Cuba because he did not use violent military actions to pacify the Cubans, and that he was not successful in the Moro Province because many of his actions to pacify the Moros were violent, and frequently brutal. Critics cite Wood's desire for career advancement, and stubborn, volatile, often arrogant attitude as primary motivations for his use of violence in the Moro Province since it differed from his actions in Cuba. These critiques ignore the unique environments Cuba and the Moro Province presented. Examining Wood's actions in their cultural and doctrinal context provides an understanding of Wood's rationale for his operational approach in each case.

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