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 approaches in each case.