With the breakup of the Soviet Union, Cuba, heavily dependent on the former superpower, plunged into a deep depression. Considering emigration their best hope, Cubans in stepped-up numbers fled to Florida without authorization, in makeshift rafts. Concerned with reelection amid mounting nativism, and seeking to avoid “another Mariel” debacle, Clinton blocked the “rafters” from coming ashore. Clinton, however, proceeded to acquiesce to pressure from earlier Cuban immigrants by extending yet new unique entitlements to Cuban immigrants. The chapter then addresses two major political crises Washington’s privileging of Cubans unintentionally unleashed, which affected outcomes of two presidential elections: one crisis involved a Cuban government shoot-down of planes CIA-trained anti-Castro Cuban immigrants flew over Cuban airspace, and the other involved anti-Castro Cuban immigrants refusing to return six-year old Elian Gonzalez to his father in Cuba after his mother drowned at sea. Instead of advancing US foreign policy interests, Cuban privileging provoked international (bilateral), along with domestic, problems.