Chicago’s Puerto Rican community, between the time it formed in the early 1950s to the grassroots activism of the late 1960s, was organized by Puerto Ricans leaders using organizational strategies that had existed in Puerto Rico ever since the beginning of US colonization in 1900. This paper investigates the conservative community structures that initially consolidated the Puerto Rican community, then turns to the egalitarian model that replaced it, which emphasized serving the community’s most marginalized members. Paying attention to religious organizations, this paper traces the service-oriented strategy used by the Hermanos Cheos in Puerto Rico through to Chicago, where members of the Cheos joined the Caballeros de San Juan and created a Christian community known as la Familia de Dios. This community that resisted conservative gender structures and created a space of community members to redeem themselves, rather than be cast out and alienated. Then the paper turns to the broader transition in community politics as many Puerto Ricans desired to build a community based on solidarity rather than hierarchy both among Puerto Ricans and with other groups who were facing the same kinds of oppression. This culminated with the politicization of the Young Lords gang and the formation of the Rainbow Coalition in 1969. The strategy they used to accomplish this arose from the religious organizations, like the Caballeros, who had come before them and their willingness to engage not only in revolutionary politics but revolutionary religion.