This article studies the intersection of sport, religion, and imperialism through the Young Men’s Christian Association (YMCA) as an extension of United States expansion into Puerto Rico after the Spanish American War of 1898. The YMCA’s emphasis on “muscular Christianity” and sports made it attractive to some locals who welcomed this feature of U.S. Americanization. This article seeks to challenge notions of imperialism and Americanization (through sport and religion) as a process not clearly defined by the dyad oppressor and victim. To the contrary, the story of the YMCA in Puerto Rico shows the ways in which YMCA leaders sought to bring progress to an “oppressed” people, while many locals welcomed a progressive institution of modern sports. My argument blurs the line between resistance and acculturation and instead proposes to see the YMCA and the early development of sport in Puerto Rico as a process of negotiations over power, identity, and culture.