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Barack Obama launched the activist “fourth quarter” of his presidency by effecting the most dramatic changes in U.S.-Latin American relations to that point in the 21st century: deportation relief for millions of mainly Latin American undocumented migrants, and the restoration of diplomatic relations with Cuba. This chapter examines how Obama, faced with determined Congressional opposition, developed a strategy of policy change through executive action that to a critical extent was made possible in these cases by close, sustained interaction with the development of Latino influence in U.S. presidential politics. This innovative strategy has implications for future U.S.-Latin American relations.