The Clinton administration’s early initiatives included public assurances that the United States posed no military threat to Cuba—to reinforce the point, U.S. officials began alerting Cuban authorities in advance of routine naval maneuvers near the island and opened low-level discussions on cooperation against narcotics trafficking. U.S. officials also dialed back the anti-Castro rhetoric. In Havana, the Cubans recognized and appreciated the change in tone. “There is less verbal aggression this year in the White House than in the last 12 years,” Raúl Castro told a Mexican reporter. Still, the administration worked overtime to assure the exile community and congressional Republicans that no opening to Cuba would be forthcoming. U.S. policy, stated Richard Nuccio, the Clinton administration’s special advisor on Cuba, was to "maintain the existing embargo, the most comprehensive we have toward any country."

Hard-liners in Congress were not reassured. Senate majority leader and Republican presidential hopeful Robert Dole declared that "all signs point to normalization and secret negotiations with Castro." In September 1995, the House passed legislation co-sponsored by Senator Jesse Helms and Representative Dan Burton that prohibited U.S. assistance to Cuba until the advent of democracy and imposed sanctions against foreign countries and corporations that did business on the island. "It is time to tighten the screws," Senator Helms announced when he first presented the bill to the Senate Foreign Relations Committee. Congressman Burton predicted that passage would be "the last nail in [Castro's] coffin."

Helms-Burton became a bitter battleground between the executive and the legislative branches. Not only did the bill "attack the President's constitutional authority to conduct foreign policy," according to a White House legislative-strategy memorandum for Clinton, "Helms-Burton actually damages the prospects of a democratic transition in Cuba, and could conflict with broader U.S. interests, including compliance with major international trade agreements ... and our commitment to respect international law." Secretary of State Warren Christopher threatened a presidential veto.

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As the Helms-Burton legislation dominated public debate on Cuba policy in the latter half of 1995, a veritable Greek tragedy played out in the skies over Cuba's coast—a tragedy set in motion by repeated incursions into Cuban airspace by a group of Cuban-American pilots known as Brothers to the Rescue (BTTR). Since 1991, the Brothers had been flying search missions for distressed Cuban rafters who had begun to flee Cuba for the U.S. by the hundreds, and then by the thousands, notifying the U.S. Coast Guard whenever a small boat or raft needed rescue.

But despite its humanitarian mission, BTTR's founder and director, José Basulto, had a history of anti-Castro violence. In April 1961, Basulto had, along with some 1,500 Cuban exiles trained by the CIA, participated in the failed Bay of Pigs invasion aimed at overthrowing Castro. In August 1962, he had positioned a boat with a 20mm cannon on its bow just off the coast of Havana and shelled the Hornedo de Rosita hotel, where he and his co-conspirators believed Castro would be dining. "I was trained as a terrorist by the United States, in the use of violence to attain goals," Basulto said in an interview with a documentary filmmaker, but he claimed to have converted to nonviolence. "When I was young, my Hollywood hero was John Wayne. Now I'm like Luke Skywalker. I believe the force is with us."