Bobby Kennedy's war on Castro.

• Author: Thomas, Evan
• Position: CIA plot to kill Fidel Castro

After World War II, when the United States was its superpower role, foreign policy was made quite informally. There was no national security staff--policy was made by Defense Secretary James Forrestal and White House advisor Clark Clifford over lunch at the F Street Club, and approved by Senate Foreign Relations Committee Chairman Arthur Vandenburg, who would receive. Undersecretary of State Robert Lovett for martinis and classified cables in his apartment at the old Wardman Park Hotel every afternoon at five.

These men did get a lot done, and much of it was good: the Marshall Plan, the Western Alliance, the Berlin Air Lift. But with freedom sometimes came excess--particularly in the world of spies. The freewheeling Central Intelligence Agency bribed officials and overthrew foreign governments without much debate by its executive branch masters, who hid behind the convenient doctrine of "plausible deniability." For them, covert action was appealing because it was cheap and, generally speaking, did not risk World War III.

But covert action and ad hoc foreign policy didn't always work as intended. This was especially true of the clumsy attempts by the CIA to get rid of Fidel Castro during the early years of the Cuban dictator's regime, from 1960 to 1964. The CIA's blunders against Castro would have been funny if they hadn't been so dangerous. The botched Bay of Pigs invasion in April 1961 and the many assassination attempts--the CIA even hired the Mafia to make a failed attempt--helped persuade Castro to accept nuclear-tipped missiles on the island in 1962, leading the world to the brink during the Cuban Missile Crisis.

The last of the CIA's plots to kill Castro is a truly weird tale. Following the Bay of Pigs fiasco, President Kennedy deputized his brother (also his attorney general) Robert Kennedy to personally oversee the CIA's campaign against Castro. Typical of the Kennedy administration's highly informal style, Bobby Kennedy bypassed CIA Director John McCone and demanded regular progress reports from Desmond FitzGerald, a dashing CIA officer who became head of the CIA Special Affairs Staff (SAS) at the beginning of 1963, charged with doing whatever he could to eliminate the Cuban leader. The bizarre events that were to unfold have fueled generations of Kennedy assassination conspiracy theorists.

The winter FitzGerald took over the Cuban operation, he made clear to his troops that he wanted results. FitzGerald's executive officer, Sam Halpern, tried to show him an organizational chart of the Special Affairs Staff, but FitzGerald said he didn't want to see it; he didn't want to be bothered with bureaucratic detail. "But Des. . .," Halpern protested. "You do it," said FitzGerald. He refused to sign the chart or even look at it.

During the summer and early fall, five commando raids were launched against Castro's economic infrastructure, in the hopes of "destabilizing" the regime. The raids were costly: Twenty-five CIA agents, Cuban exiles recruited as commandos, were killed or captured. Though it was doubtful that the commandos would bring down Castro by knocking down some telephone poles or by petty acts of sabotage (the negligible Cuban underground was instructed to leave faucets running and light bulbs burning to waste energy), FitzGerald was determined to keep trying.

"We were saying, `Please don't expect that any one of these things is going to be a catalyst'," recalled Ted Shackley, the Miami station chief. "But FitzGerald felt under pressure to make these things work, and the pressure came from Robert Kennedy. He'd say, `I saw Bobby,' or `I ran into Bobby. I saw him in Middleburg. Here's what we got to crank up for next month.' We would say, tactfully. We can make it work. But the question is, will these events bring Castro down?'"

Halpern said he began to "dread coming in to work in the morning," especially Monday mornings after FitzGerald had all weekend to "run into" Kennedy and think up his own schemes--"all these harebrained ideas," as Halpern described a series of plots that would seem like black comedy when they surfaced later during the Church Committee hearings. "[Bobby]," said Halpern bluntly, "reinforced [FitzGerald's] worst instincts."

By the time FitzGerald took over the Cuba operation, the CIA had pretty well given up on using the mob. The plots of Bill Harvey, FitzGerald's predecessor as head of the Cuba group, to enlist the Mafia had gone nowhere. In the spring of 1962, Harvey had given John Rosselli, his mob contact, four poison capsules and assured him "they would work anywhere and at any time with any thing." Harvey and Miami station chief Shackley also rented a U-Haul truck, filled it with $5,000 worth of explosives and weapons, left the van in a parking lot, and handed the keys to Rosselli.

But Rosselli's Cuban agents were unable--or perhaps never really tried-to kill Castro. In February 1963, just as FitzGerald was taking over Cuban operations, Harvey had a drunken farewell dinner with Rosselli, with whom he had become pals (They shared a hatred of Bobby Kennedy. FBI gumshoes, who had Rosselli under routine surveillance, looked on in disbelief.

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