The attempted isolation of Cuba, the vain resolve to overthrow or punish the Castro regime, has been perpetuated for over half a century by presidents of both parties. Granted, Jimmy Carter, Bill Clinton, and Obama have each ventured a measure of détente without fundamentally reversing a course that has brought only persistent failure. And in the mid-1990s, when the Cuban Air Force shot down two airplanes dispatched by a Miami – based exile group, Brothers to the Rescue, which had previously dropped hundreds of thousands of leaflets over Havana, the United States reverted to a hard anti–Castro line. Congress passed the Helms–Burton Act to tighten the sanctions regime and write it into the law. Democratic opposition had blocked the bill in 1995, but in the wake of attack Bill Clinton, anxious to carry Florida in his reelection bid, swiftly signed it into law.
Most Democratic presidents – and perhaps secretly even George H.W. Bush – have understood the folly of U.S. policy toward Cuba. Ironically, John F. Kennedy, who had tried overtly and covertly to topple Castro, seemed to be moving in a decisively different direction by 1963. He dispatched unofficial envoys to discuss rapprochement; one of them, French journalist Jean Daniel, was with Fidel Castro when the news of Kennedy’s assassination came. “This is terrible,” Castro exclaimed. “There goes your mission of peace.” Not long after, normalizing relations with Castro would become a third rail in politics with pivotal Florida in the sway of a growing population of violently anti-Castro Cuban-American citizens.”