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How the CIA’s Cuba Debacles Brought the Future Watergate Conspirators Together

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In the fall of 1961, the Agency moved from its shabby scattered offices in Foggy Bottom to a gleaming seven-story office block tucked in the woods of suburban Langley, Virginia, five miles northwest of the White House. It was one of the largest office buildings in the country, a keystone of America’s imperial ambitions as memories of World War II faded and the president proclaimed a New Frontier. The new headquarters signaled the Agency’s ascendancy in the structure of national power. Yet the modernist gleaming architecture could not erase the existential humiliation of the Bay of Pigs defeat.


After a decent interval of seven months, Kennedy eased Dulles and Bissell out of their jobs. To replace Dulles as director of Central Intelligence, Kennedy named John McCone, a curmudgeonly corporate executive and Republican then serving as chairman of the Atomic Energy Commission.

The Bay of Pigs debacle vindicated Helms’s prudence and ensured his promotion to the job he thought he should have gotten three years before. After fifteen years of running secret operations, Helms was the consensus choice to replace Bissell as the DDP, deputy director of plans. (Inside the Agency the initials could refer either to the Directorate, which consisted of five regional divisions with desks for every significant country in the world, or to the man who headed it.)

The Bay of Pigs debacle vindicated Helms’s operational prudence and insured his promotion to the job he thought he should have gotten three years before. On Helms’s first day as DDP, McCone told him he was in charge of Cuba. “Yes, sir,” said Helms. As a dutiful civil servant, he often presented himself as a veritable butler of espionage who served up whatever information or action his political masters called for.

Helms was also a man of action. Three Agency operatives had been arrested in Havana in September 1960, while mounting an audio operation against the offices of the Chinese news service. They were sentenced to ten years in jail, though not identified as CIA agents. Helms asked John Mertz, deputy chief of the Counter-intelligence Staff, to come up with a plan to free the prisoners. Mertz consulted with his boss, James Angleton, counterintelligence chief, who supplied him with some “underworld” connections in Havana. Mertz then tasked James McCord, deputy chief of the Security Research Staff in the Office of Security, to scope out the prison and execute the escape. As McCord later explained, his agents “gained entry to the prisons” and returned to the United States “with data acquired,” but the captured men were freed in a prisoner exchange before any rescue operation could be mounted. McCord was credited with being “an actual case officer for Cuban agents” from 1960 to 1962. Helms surely knew of his work, at least in passing. McCord’s road to Watergate had begun.

Helms’s greatest challenge in his new job was serving the two very different brothers in the White House, John and Robert Kennedy.

“John Kennedy was urbane, objective, analytical, controlled, contained, masterful, a man of perspective,” wrote historian Arthur Schlesinger, an OSS veteran and friend of Helms, who worked in the White House. “Robert, while very bright and increasingly reflective, was more open, exposed, emotional, subjective, intense, a man of commitment.” Novelist Gore Vidal, a friend of First Lady Jacqueline Kennedy, was less charitable. Bob Kennedy’s “obvious characteristics are energy, vindictiveness, and a simplemindedness about human motives which may yet bring him down,” Vidal wrote. “To Bobby the world is black or white. Them and Us. He has none of his brother’s human ease; or charity.”

Personally, Helms preferred the president. JFK’s dry wit and detached style were closer to his own. Professionally, he had to deal with Bob much more often, because of president had made his brother the point man for his post–Bay of Pigs Cuba policy. Helms appreciated Bob’s anticommunism which liberals like Vidal found simplistic. What bothered the deputy director was Bob’s naivete.

“Within a few weeks of Bob Kennedy hammering on us for results, I realized he had but a slight idea of what was involved in organizing a secret intelligence operation,” Helms wrote in his memoir. “He appeared to equate the director of the Central Intelligence position with that of the chief of the General Staff.” Helms thought RFK something of a fool, but he kept his opinion to himself until late in life.


Meanwhile, at his Tudor-style home in Wesley Heights in northwest Washington, Nixon brooded and scrawled on his legal pads. He conferred with Kennedy after the humiliation of the Bay of Pigs and urged him to invade Cuba, “to find a proper legal cover” and “go in,” advice that JFK spurned. He called friends and drank and brooded some more. Nixon couldn’t bear the thought of practicing law, which was the most common advice he heard after leaving the vice presidency. Instead, he conceived of a plan to return to California. He would write a short accessible political testament like JFK’s Profiles in Courage. Then he would run for governor of California, where he had already won three elections. Then he would have a rematch with JFK in 1964, and the Bay of Pigs would help him make his case.

Pat Nixon thought she would have more time with her husband after he left the vice presidency. Daughters Julie and Tricia thought they would see more of their father. They saw less. “As usual, the ones who suffered most and most silently were my family,” he wrote.

It was his secretary Rose Mary Woods, more than anyone, who sustained Nixon’s enormous ambition. Like many young women, Woods moved to Washington during World War II to get a good job. As a secretary to the Select House Committee on Foreign Aid in 1948, she had been impressed by the precision of Congressman Nixon’s expense accounts. When he was elected to the Senate in 1950, she accepted an offer to become his secretary.

Nixon felt lucky. “Next to a man’s wife, his secretary is the most important person in his career ,” Nixon said of Woods. “She has to be flawlessly proficient at shorthand and typing. She has to have the quite different skill of making hundreds of decisions a day for her employer, and she has to know just what decisions not to make as well. . . . She is the balance wheel of the whole office.”

From the start, Woods saved Nixon from his self-defeating instincts. In 1952, when Eisenhower chose Nixon to be his running mate on the Republican ticket, he was hit with a newspaper story reporting that his supporters in California had put aside money for his personal use, a “slush fund” in the lingo of headlines. The story was essentially accurate. Nixon, a man of modest means, liked having money, and his backers kept him flush. To save his candidacy, Nixon gave a speech, broadcast on the radio and the increasingly popular medium of television. His self-pitying performance, complete with reference to the family dog, Checkers, was a hit with Republican voters. When Eisenhower responded favorably but did not commit to keeping Nixon on the ticket, the sulking candidate wrote a telegram of resignation. Woods knew better than to send it.

With Woods’s constant assistance, Nixon was both running for governor and writing the memoir that would become the best-selling book Six Crises. He yearned—burned to return to power. He moved his family to swank Bel Air, California, in the foothills of the Santa Monica Mountains. He began meeting with a ghostwriter every morning. One day a brushfire swept through the neighborhood, forcing Nixon to scurry to his car while carrying framed photographs, his precious memories in danger. He was a witness to conflagrations, a man close to the flames.


Helms was a manager, a man with a neat desk. He cleaned house in the Cuban operation, relying on his trusted deputy, Tom Karamessines, to execute his every order. Tom K., as he was known, came from Bridgeport, Connecticut, attended Columbia University in New York, and graduated from the law school in 1941. In the war, he joined the OSS and opened its station in Athens. A taciturn pipe smoker, Tom K. was renowned for his covert skills. “On such matters as letter drops, cutouts, safe houses, two-time codes, ‘magic,’ and other tricks and treats of the espionage trade,” one journalist wrote, “Karamessines is said to have no peer.” Tom K. would serve quietly at Helms’s elbow for the next decade.

Helms relieved Jake Esterline, chief of the Cuba task force. He replaced him with Bill Harvey, the chief of the Berlin base, whom Helms regarded as perhaps the finest operations officer in the DDP. He brought in Ted Shackley, a brusque deputy of Harvey’s, to run the Miami station. He sent his energetic protégé David Phillips to Mexico City to wreak havoc on the Cuban embassy, Castro’s first intelligence outpost in the western hemisphere. Helms had bad news for Howard Hunt. “It was made abundantly clear to me in a very pleasant way that I was to have nothing further to do with Cuba operations,” Hunt recalled.

Helms conferred a consolation prize on Hunt more appropriate for his literary talents. He assigned him to serve as covert action chief in the newly created Domestic Contacts Division, where he supervised what a later generation would call “soft power” activities. Hunt later testified that he took over the Agency’s relationship with Frederick Praeger Publishing Company, which published books that aligned with the Agency’s interests but were not “economically feasible.” With subsidies from Langley, Praeger generated books that advanced the Agency’s mission. In this domestic propaganda operation, Hunt reported to Karamessines. Helms took care of his pal.


The deputy director had to deal with the mess left by the inexperienced Dick Bissell. Bob Maheu might have been the right man to introduce Agency officers to organized crime figures. But telling the amoral ex-FBI agent the specific and lethal nature of their interest was a mistake for which the Agency soon paid. As Maheu’s friend, Johnny Rosselli, put it, “If somebody gets in trouble and they want a favor from the G [meaning the U.S. government] we can get it for them. You understand. We have the government by the ass.” Bob Maheu—no surprise—had a feel for blackmail.

Helms knew this terrain better than most gentlemen.

“Let’s leave aside the notion of theology and the morality of all good men for just a moment,” he dilated for TV talk show host David Frost. “If you hire someone to kill somebody else, you are immediately subject to blackmail, and that includes individuals as well as governments.” As Helms knew full well, Maheu was one of those individuals. Maheu had a problem, and he wanted the CIA to fix it. It seems that Sam Giancana, while negotiating with the Agency about the Castro hit, expressed concern that his girlfriend, pop singer Phyllis McGuire, was getting “too much attention” from comedian Dan Rowan, who was performing in Las Vegas. Giancana asked Maheu to bug Rowan’s hotel room to determine “the extent of his intimacy with Miss McGuire,” as the CIA inspector general chastely put it. Maheu hired an experienced “wire man” to plant the bug, but the man wasn’t experienced enough. Hotel security officers nabbed him in the act. When he called Maheu for help, the FBI was listening in. The Bureau decided to charge both men with violating federal wiretapping statutes. Maheu let his friends at the CIA know that, if prosecuted, he would start talking about the Agency’s scheme to kill Castro. The charges were soon dropped. Blackmail worked.

The CIA men had to explain the story to Attorney General Bob Kennedy in all of its tawdry detail. Kennedy listened impassively, irked by the means, not the ends. He needed the Agency to avenge the Bay of Pigs, the biggest blot on his brother’s record, in time for the 1964 campaign. He expressed no view on the killing of Castro, but loathed the choice of assassins. “I trust that if you ever try to do business with organized crime again—with gangsters—you will let the Attorney General know,” he said.

Dick Helms had other plans. He put Bill Harvey, former chief of the Berlin base, in charge of ZR/RIFLE, the Agency’s new assassination program. William King Harvey, a former FBI agent from Indiana, was fat, brilliant, and dangerous. Some called him America’s James Bond, though he was hardly handsome or debonair. His biographer dubbed him a “flawed patriot.” His longtime colleague, John Whitten, chief of the Mexico desk, called him a “gun fanatic” and a “thug.” Helms thought him indispensable. “He was much more than heavyset,” Helms wrote in his memoir. “A more pertinent description would have concentrated on his phenomenal memory, aggressive approach to business, and knowledge of Soviet espionage in the United States.”

Helms authorized Harvey to provide a trailer full of weapons to Johnny Rosselli for the purpose of killing Castro. Harvey, a savvy bureaucratic operator when sober, asked if he should inform director John McCone about the mission. Now a man of considerable guile, Helms said no. Nor did Helms tell Bob Kennedy that Harvey was plotting with Rosselli. In his memoir, the older and presumably wiser Helms wrote, “In peacetime the assassination of troublesome persons is morally and operationally indefensible. There are invariably other solutions, not the least of which is time—time for the immediate and sometimes fierce tactical pressure to subside or for the problem to be reevaluated or another solution found.” Helms would assure interviewer David Frost, “I have never believed in assassination.”

In 1962 and 1963 at least, Helms believed, as he himself conceded. “We were under great pressure to make contacts in Cuba,” he told Frost. “I let the pressure to do something—because we didn’t have very many contacts—overwhelm my judgment. We never should have gone forward the second time with that Rosselli thing. When I found out about it, I should have corked it.”

Instead, he uncorked it—he authorized Harvey to work with the gangster Rosselli and he didn’t bother to tell Bob Kennedy, who had made clear he wanted to know if the CIA was relying on organized crime figures. Helms later said he didn’t feel the need to tell RFK about his assassination activities because he viewed his job as serving as “a secret screen between overt officialdom and some of the more dubious, or self-serving, denizens of the nether depths.” Helms, it seems, didn’t want to burden the attorney general with the unseemly details of how he defied his order. It was a matter of protecting the White House, he said. As novelist Thomas Mallon observed, Helms was slippery, even for a spy.


From SCORPIONS’ DANCE: The President, the Spymaster, and Watergate, by Jefferson Morley. Copyright © 2022 by the author and reprinted by permission of St. Martin’s Publishing Group.


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