What happened? How did Lansdale plummet so quickly and so far from the heights of power and prestige? His career—like many other promising elements of the Kennedy administration—foundered on the island of Cuba, with ramifications that would in time be felt on the other side of the world in Vietnam.

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Lansdale received a thankless assignment at the end of 1961: to overthrow Fidel Castro, the bearded young revolutionary who in 1959 had had seized power in Havana. The Kennedy administration initially had tried to topple Castro, who was seen as a communist threat in America’s “backyard,” by backing a CIA-organized invasion of exiles at the Bay of Pigs in April 1961. That had turned into a fiasco. Now the Kennedys were hell-bent on getting rid of Castro any way they could, and they saw Lansdale as just the man for the job. His lack of experience with Cuba was seen as a recommendation: He was not tainted by the Bay of Pigs operation, which he had opposed.

Lansdale, who by now was special operations chief at the Pentagon and no longer on the CIA payroll, was assigned as chief of operations of a top secret, interagency task force known as the Caribbean Survey Group—soon to be designated, for cover purposes, Operation Mongoose. Lansdale had to rely on liaison officers from the State Department, the CIA, the U.S. Information Agency, the Defense Department, and other government agencies that were supposed to voluntarily cooperate with him. That ideal was not easy to achieve in practice, given the level of skepticism within the CIA and State Department toward the project in general and to Lansdale in particular—he had long feuded with bureaucratic rivals. “It was the most frustrating damn thing I’ve ever tackled,” Lansdale wrote two years later. “I was given full responsibility for a US effort, but had no say on disciplining or giving orders to US personnel working in this effort. Most of these were State and CIA folks who made it plain to me that they hated my guts. So about once a week I would formally request relief from this duty, and be told that this was unacceptable.”

Attorney General Robert F. Kennedy, who took on Castro’s overthrow as his personal project, put intense pressure on Lansdale to achieve results. At meeting after meeting, the president’s younger brother stressed that there had to be “maximum effort” and that “there will be no acceptable alibi” for failure. “Let’s get the hell on with it,” he would say. “The president wants some action, right now.” His performance at Mongoose meetings reminded the CIA’s deputy director, Marshall Carter, of “the gnawing of an enraged rat terrier.”

After having sifted through various ideas to topple Castro, Lansdale on February 20, 1962, produced a detailed, if delusional, plan. The operation was supposed to start in March and culminate in October with what Lansdale described as the “touchdown play”: Castro’s overthrow. How on earth could Lansdale expect the weak and divided Cuban opposition, decimated at the Bay of Pigs, to prevail within less than a year? He prided himself on being unafraid to tell unpleasant truths “point blank” to his superiors, and he often had in Vietnam, but when it came to Cuba he succumbed to the temptation to tell his superiors what they wanted to hear in the hope that they would allow him to return to Saigon to once again chart American policy in South Vietnam. In his own defense, the best that Lansdale could say was: “I was hopeful and I put it down as a date without believing myself that it was a firm date—it was a prospective date of the early fall of 1962.”