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The arrival of over 1-million Puerto Ricans in Florida is altering Latino politics in the state. In fact, Puerto Ricans are now the second-largest Latino group and the second-largest Latino electorate in the Sunshine state. Puerto Ricans’ migratory shift away from historic destinations in the Northeast and Midwest to the South means they have settled in a distinct racial and political context. This paper examines the making of Puerto Rican and Latino politics in Orlando, Florida. To do so, it draws on ethnographic data collected during voter engagement campaigns that targeted Puerto Rican and Latino communities and voters during the 2016 presidential election. It also draws on in-depth interviews conducted with voter engagement project leaders and canvassers. This study finds the making of Puerto Rican and Latino politics in Orlando metro is a dynamic process characterized by tensions, negotiations, and cooperation throughout various stages of politics-making. While shared structural barriers (racialization and political marginalization in Florida) are often the source of panethnic collaboration, funders, national organizations, and political elites exert significant influence in shaping the contours and scope of Latino voter engagement and mobilization. Despite these political dynamics, Puerto Rican and Latino leaders emerge as political entrepreneurs who draw on political toolkits acquired in Puerto Rico, Latin America, and stateside communities to navigate structural constraints and mobilize Puerto Rican and Latino voters. Overall, this paper captures how Puerto Ricans and Latinos exert political agency in a critical region of the state and one that is consequential for national politics.