A strong southeasterly wind was whipping the surface of the Caribbean on the night of March 11, 1962, as the sport fishing boat approached the Cuban shoreline. The 30-foot Forest Johnson Prowler was one of the strongest, fastest wooden boats available, but its engine was quiet enough to allow its three crew members to bring it to within a mile of the shore. Those sailors were some of the most experienced mariners in the CIA’s small naval force of Cuban expatriates, but even they were not allowed to see the faces of the two hooded agents who clambered over the boat’s side into a 16-foot fiberglass canoe packed with supplies.
The rough sea almost ended the agents’ mission before it began, when their canoe capsized as soon as they got in, spilling its precious cargo of men and gear into the swelling ocean. The crew scrambled to retrieve the packages, which were waterproofed cans wrapped in plastic. With the canoe righted and the gear stowed again, the two agents climbed back in and managed to stay upright. Pointing the canoe toward the coast, they paddled off into the gaping mouth of the San Diego River.
The canoe had been the idea of Tom Hewitt, the agents’ case officer in the CIA’s huge Miami station, where he waited for word of the mission. Agency rules forbade him to take part in the team’s infiltration, but he felt a deep responsibility for the pair, a principal agent whom he had trained to manage a network of subagents, and his radio operator. It would be Hewitt’s job to guide their actions from afar, now that they were back in their homeland. A 10-year veteran of the CIA, Hewitt had spent the previous six months teaching the principal agent everything he knew about how to run an effective espionage network, doing all he could to mitigate the substantial risks that the agent would have to take in Fidel Castro’s Cuba. The team’s mission was to establish a network that could be used to gather intelligence and, if necessary, to foment counterrevolution against the Castro regime. Getting rid of Castro was a high priority for the administration of President John F. Kennedy and for the CIA. Hewitt knew this was an important mission, but he could not have imagined that his team would soon play a vital role in preventing nuclear Armageddon.
When the Soviets secretly deployed medium and intermediate-range ballistic missiles to Cuba in the summer of 1962, it set off a chain of events that almost led to nuclear war. Scores of books and thousands of articles have been written about the Cuban missile crisis, yet Tom Hewitt’s name is absent from all of them. Photos of the missile sites taken by U-2 spy aircraft in October of that year are almost always cited as the key intelligence breakthrough that gave the United States a priceless advantage during the nuclear standoff. A Google search for “Tom Hewitt and Cuban missile crisis and CIA” turns up a single reference in a book by one of his old CIA bosses that refers to his role running “road-watch” teams during the United States’ secret war in Laos later in the decade.
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