What effect did the special entitlements offered Cubans by eleven Presidents have on actual Cuban immigration? Rates of immigration from Cuba and Haiti, and the Dominican Republic, another Caribbean country of roughly the same population, are compared. The chapter also addresses “lessons learned” about over half a century of US inequitable treatment of immigrants, about how “path-dependent” privileging may be, about use and abuse of Presidential discretionary power to favor certain immigrants and disfavor others, and about how and why immigration and immigrant-related policies and practices may persist long after justified by their initial rationale. “Lessons learned” also include explanations about how and why a country as powerful as the United States has been limited in its control over immigration. The Cuban government, with far less resources, as well as ordinary Cubans, in the United States and Cuba, have also shaped US policies.