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The arrival of over 1-million Puerto Ricans in Florida is altering Latino politics in the state. 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 vastly different racial and political context. This presentation examines the making of Puerto Rican politics in Florida by focusing on the political experiences of Island born/raised Puerto Ricans. I draw on 75 in-depth interviews with Puerto Ricans conducted in Orlando metro during the 2016 election cycle. I find three themes explain key aspects of Island Puerto Ricans’ political transition to, how they define their political position in, and how they enact politics in Florida: 1) legacies of colonial citizenship; 2) negotiating stateside political contexts and (un)defining political identities; and 3) navigating political (dis)interest and (dis)engagement. I argue the experience of a colonial politics in Puerto Rico and ethnoracial exclusion in Florida converge to shape how Island Puerto Ricans do politics in the largest swing state of the U.S.