Clinton’s successor, George W. Bush, further expanded entitlements for Cuban immigrants, indebted to Cubans in Florida who helped him get elected in 2000 when the state’s vote was highly contested. President Obama enforced Bush’s policies, plus those of earlier administrations. However, he was the first president to extend no new entitlements to Cuban immigrants. Although Fidel had fallen ill and relinquished power to his younger brother Raul, and then died in 2016, Cubans continued to enjoy the unique entitlements initially introduced to bring Castro’s regime to heel in the throes of the Cold War. Then, during his last full week in office Obama ended Cuban exceptionalism “as we knew it” for over half a century. The chapter details the policies Obama retracted and how he capitalized on a growing social and political divide among Cuban Americans to retract entitlements. The chapter also details how the Bush and Obama administrations expanded Haitians “path of disprivilege,” despite political violence, poverty, and persecution plaguing Haiti. Cuban–Haitian inequities continued.