by Gus Russo
With his intellectual curiosity, and his knowledge of history and other leaders’ mistakes, John Kennedy grew remarkably as a statesman during his 34 months as president. He took courageous steps toward peace with many adversaries. But Cuba remained the exception. As his father opined, “Cuba gave this administration a chance to be great.” Tragically, it was an opportunity not seized.
The Kennedy Connections
John F. Kennedy inherited more than a family characteristic for stubbornness. He inherited his family’s resources, its wealth, and connections as high as the CIA and as low as the Chicago underworld. Joseph Kennedy had built a network of trustworthy men, which JFK expanded while he occupied the highest office in the land. The men in this large network would protect him during his presidency (and after his death), but couldn’t protect him from the repercussions of his brother’s actions, taken either on his behalf or according to his orders. This network of powerful friends has been pointed to as evidence of an anti-Kennedy conspiracy. The truth is just the opposite.
Patriarch Joe Kennedy founded a Kennedy tradition when he entered the bootlegging business in the 1920’s. His relationship with the Mafia would grow, culminating when he approached the underworld for its support in JFK’s 1960 presidential campaign. Joe Kennedy’s contacts in that area would also prove invaluable when Robert Kennedy was later looking for “unofficial” intelligence opportunities in Cuba. The Mafia had been almost entirely shut out by the Castro regime, and they very badly wanted to return to Cuba. RFK was not opposed to using them to get what he and his brother were after.
The Kennedys had informal bonds with CIA members long before John F. Kennedy was inaugurated. Robert Kennedy’s wife’s family, the Skakels, maintained close relationships with CIA officers. In 1966, the closeness of the Skakels with the CIA was noted when George Skakel, Jr. (then running Great Lakes) and three friends chartered a plane for a hunting trip in Idaho. When the plane crashed, killing all aboard, it was reported that 15-year CIA veteran Lewis Werner was one of the victims. In charge of the St. Louis division of the CIA at the time, Werner often traveled to Cuba with Skakel to hunt wild boar.
In addition, a variety of New England liberals such as Allen Dulles, Des FitzGerald, Richard Bissell, Richard Helms were part of a social/intellectual clique that included Joseph P. Kennedy. CIA executive Bill Harvey referred to this group as “Fifth Avenue cowboys.” As historian Burton Hersh points out, “Most of the leadership of the CIA was enlightened, preponderantly Democratic, with emerging senior managers like Tracy Barnes and Dickie Bissell quite dedicated social reformers.”151 Comparisons to the Kennedys are inescapable.
The Kennedy brothers had also preserved a long-lasting association with Allen Dulles, then CIA Director. Letters in both the Kennedy and Dulles collections reflect that John and Robert Kennedy maintained correspondence with both Dulles brothers from at least 1955. Traveling in the same social sphere, Allen Dulles and John Kennedy were “comfortable with one another and there was a lot of mutual respect,” Richard Bissell said in an interview. In fact, Kennedy was known to regard Dulles as a legendary figure. Historian Herbert Parmet wrote, “Dulles often went to the Charles Wrightsman estate near Joe Kennedy’s Palm Beach House. As far back as Jack’s early days, they socialized down in Florida, much of the time swimming and playing golf.”152 Dulles himself said, “I knew Joe quite well from the days when he was head of the Securities and Exchange Commission.”153
But Papa Joe Kennedy’s relationship with Dulles extended far beyond that of neighbor and occasional golf buddy. On January 13, 1956, when Allen Dulles was CIA Director, Joseph Kennedy was appointed to President Eisenhower’s Presidential Foreign Intelligence Advisory Board (PFIAB).154 “PFIAB is a sort of holding ground for people who couldn’t obtain, or didn’t want, Congressional approval [to serve the U.S. government],” explains Colonel Alan D. Campen, who served under President Reagan as Director of Command and Control Policy in the office of the Secretary of Defense.155 Historian Michael Beschloss adds, “After exerting himself to win appointment to Eisenhower’s intelligence board, he [Joe Kennedy] improved his acquaintance with Dulles.”156
Among other commonalities, Joe Kennedy and Allen Dulles were both outspoken isolationists at the start of World War II. Kennedy was often called pro-Nazi (by, among others, Lyndon Johnson) when he publicly insisted that the German-English “feud” had nothing to do with U.S. interests.157 Likewise, Dulles, whose law firm, Sullivan and Cromwell, represented many German and U.S. investors, told businessmen who belonged to the German SS that he believed that many of their objectives were well-founded. At one point, Dulles remarked to a German SS member that he was “fed up with listening all the time to outdated politicians, émigrés, and prejudiced Jews.”158
Dulles first met Jack Kennedy at the Kennedy Florida compound in 1955. They became fast friends. “Our contact was fairly continuous,” Dulles later said. “When [JFK] was in Palm Beach, we always got together.”159 Jack came to revere both Dulles’ intellect and accomplishments.
Robert Kennedy, too, was clearly impressed with Dulles. Regarding his performance at the time of the Bay of Pigs, Robert Kennedy later recalled, “Allen Dulles handled himself awfully well, with a great deal of dignity, and never attempted to shift the blame. The President was very fond of him, as I was.”160 He elaborated to historian Arthur Schlesinger, “He [JFK] liked him [Dulles]—thought he was a real gentleman, handled himself well. There were obviously so many mistakes made at the time of the Bay of Pigs that it wasn’t appropriate that he should stay on. And he always took the blame. He was a real gentleman. JFK thought very highly of him.”161
Dulles kept a variety of Kennedy secrets from the public. For example, when John Kennedy won the election in November 1960, the CIA under Dulles conducted a background investigation of Kennedy in anticipation of his first intelligence briefing as President-elect on November 18. Such investigations were designed to predict how the subject would respond when informed of the full range of CIA operations, and to show Dulles the most effective method of appeal. Prepared by CIA psychologists, the study included hot evidence from the FBI: the indiscretion of a youthful Jack Kennedy, at the height of World War II, with alleged Nazi spy Inga Arvad Fejos.162 In 1942, while serving in the Office of Naval Intelligence in Washington, Jack Kennedy had established this potentially dangerous liaison. The FBI, which had wiretapped Arvad, initially compiled the file. Historian Thomas Reeves wrote:
When Jack’s relationship with the woman became known to Navy officials, the assistant director of the Office of Naval Intelligence wanted to cashier the young ensign from the Navy. A witness remembered the officer being “really frantic.” Reminded of Joe Kennedy’s prestige, however, the official eventually calmed down and consented merely to give Jack a speedy transfer to an ONI outpost in Charleston, South Carolina.163
(FBI sources state that it was Hoover’s direct pressure that brought about the transfer.164 The potential value of this kind of political dynamite was most assuredly never lost on the FBI Director. It was just the kind of file that kept Hoover’s power inviolate for so long.165)
Dulles’ decision, or favor, to keep this matter secret was quite possibly rewarded later, when Kennedy, as president-elect, retained Dulles as CIA Director. It may also have played a part in Kennedy’s initial refusal to accept Dulles’ resignation after the Bay of Pigs fiasco.
The CIA after the Bay of Pigs
“In the course of the past few months I have had occasion to again observe the extraordinary accomplishments of our intelligence community, and I have been singularly impressed with the overall professional excellence, selfless devotion to duty, resourcefulness and initiative manifested in the work of this group.”
—President Kennedy, in a letter of commendation to new CIA Director John McCone, January 9, 1963
After thinking it over, it was clear to John Kennedy that the blame for the Bay of Pigs was largely his and not the CIA’s. And although Kennedy needed public sc
apegoats in his administration, he drew the line at a public indictment of the original Eisenhower-era planners of the invasion. Kennedy’s Secretary of State, Dean Rusk, later testified, “President Kennedy was very angry when some people around him tried to share responsibility with President Eisenhower because President Kennedy knew that he and his senior advisors had a chance to look at that and made their own judgment on that, and he did not like the idea of having to share the buck.”166
Although Kennedy’s threat to “splinter the CIA into a thousand pieces and cast it to the winds” has long been used to support theories that the CIA had reason to hate JFK, just the opposite is true. Kennedy’s “threat” was a knee-jerk reaction to the failed invasion. Years later, E. Howard Hunt, the CIA’s liaison to the Cuban exiles, surmised, “For him [Kennedy] to have said that was probably a way of disguising from himself the fact that he himself was responsible for the fiasco, and I’m sure that’s something that haunted him for the rest of his days.”167
All of John Kennedy’s other statements regarding the CIA were nothing short of glowing. On November 28, 1961 Kennedy went to Langley, Virginia to dedicate the CIA’s new headquarters, which came to fruition under the outgoing Director, Allen Dulles. Addressing the large throng, Kennedy said:
I want, first of all, to express my appreciation to you all for the opportunity of this ceremony to tell you how grateful we are in the government and in the country for the services that the personnel of this Agency render to the country. It is not always easy. Your successes are unheralded—your failures are trumpeted. I sometimes have that same feeling myself But I am sure you realize how important is your work, how essential it is—and, in the long sweep of history, how significant your efforts will be judged.
In addition to the dedication, Kennedy had planned a surprise for his loyal friend. Dulles’ biographer, Peter Grose, described the event:
Allen greeted the presidential helicopter at the landing pad hidden among the trees of the campus. Interrupting the carefully scripted ceremony that followed, with more than six hundred CIA professionals in attendance, Kennedy turned to the dais behind him. “Would you step forward, Allen.” On his lapel he pinned the National Security Medal. Short of knighthood or lordship, it was the highest honor of the United States government.168
Turning to address Dulles, Kennedy said, “I want to express my appreciation to you now, and I am confident that in the future you will continue to merit the appreciation of our country, as you have in the past.” The next day, JFK dashed off a letter expressing his great admiration and affection for Dulles. In closing, Kennedy wrote, “You leave behind you, as witness to your great service, an outstanding staff of men and women trained to the nation’s service in the field of intelligence.” In what appears to be a genuinely heartfelt letter to his old friend Dulles, the President added, “I am sure you know you carry with you the admiration and affection of all of us who have served with you. I am glad to be counted among the seven Presidents in whose administrations you have worked, and I am also glad that we shall continue to have your help and counsel. . . Your integrity, energy, and understanding will be a lasting example to all.”169 Two years later, in the wake of JFK’s assassination, Dulles’ kinship with John Kennedy would play a role in Dulles’ decision to withhold critical information from his fellow Warren Commission members.
On March 1, 1962, JFK would similarly honor Bissell with the same National Security medal. In ceremonies at the White House, Kennedy made it clear that he still held Bissell in high esteem. In part, Kennedy said:
During his more than twenty years of service with the United States government, he has invested a rich fund of scholarship and vision. He has brought about returns of direct and major benefit to our country. In an area demanding the creation and application of highly technical and sophisticated intelligence techniques, he has blended theory and practice in a manner unparalleled in the intelligence profession. Mr. Bissell’s high purpose, unbounded energy, and unswerving devotion to duty are benchmarks in the intelligence service.170
The Kennedys and the CIA
After the Bay of Pigs, as both he and his brother Robert began to understand the intended role of the CIA, John Kennedy would oversee one of the greatest budget increases for the intelligence community in U.S. history. “You have to always bear in mind how the Agency was originally set up,” instructs one high-ranking Agency official. The CIA, he reminds us, was instituted as the intelligence arm of the Executive branch—the President and official Washington have never been confused about that fact. First conceived by President Harry S Truman, the CIA was established and organized by the National Security Act of 1947 (Truman submitted it to Congress, which passed it on July 26, 1947).
The CIA’s charter is unambiguous in stating that the Agency would function only in response to directives of the President and of the President’s own intelligence apparatus, the National Security Council. Nowhere in the charter is there any inference that the CIA would be allowed to initiate policy. JFK, a close student of history, was undoubtedly aware of the Eisenhower-CIA partnership that had toppled regimes in both Iran and Guatemala. The Directors of the CIA, appointed by the President, take their loyalty to the President seriously, and often have performed tasks against their own better judgment at their bosses’ behest.
In return for this loyalty, Kennedy often went out of his way to shield the CIA from unwelcome scrutiny. At a news conference in November 1963 (six weeks before his death), Kennedy responded to a question regarding the CIA. A newsperson had asked Kennedy if the CIA was conducting unauthorized activity in South Vietnam. Kennedy rose to its defense, saying:
I think that while the CIA may have made mistakes, as we all do, on different occasions, and has had many successes which may go unheralded, in my opinion in this case it is unfair to charge them as they have been charged. I think they have done a good job.
Robert Kennedy also knew where the buck stopped. In 1967, when the CIA was criticized for giving illegal financial support to the National Student Association, Bobby refused to let the CIA take the rap. He went on record as saying that the CIA policies were approved at the highest levels of presidential administrations. “If the policy was wrong,” Bobby said, “it was not the product of the CIA but of each administration.”171 When Kennedy family friend Jack Newfield tried to goad Bobby into criticizing the Agency, Bobby again rose to its defense, saying, “What you are not aware of is the role the CIA plays within the government. During the 1950’s. . . many liberals found sanctuary in the CIA. So some of the best people in Washington, and around the country, began to collect there. One result of that was the CIA developed a very healthy view of Communism, especially compared to State and some other departments. So it is not so black and white as you think.”172
The Kennedy brothers, Bobby more than Jack, soon became smitten with the clandestine world the CIA inhabited. Author and intelligence expert John Ranelagh most accurately summarized the relationship. According to one CIA man with whom Ranelagh spoke, “Robert Kennedy, in his shirtsleeves, delved into the inner workings of the agency. In the end, he did not shake it up as his brother had wanted, but fell in love with the CIA and the concept of clandestine operation.” Ranelagh added:
Jack Kennedy realized, as he told Clark Clifford—an influential and trusted Kennedy advisor and Democratic power broker—“I have to have the best possible intelligence,” and soon reversed his decision to punish tine CIA. Both brothers saw that alone of the agencies of government the CIA was willing to take action and had tried to do in Cuba what the President wanted. The Bay of Pigs failure meant that the agency would not resist tighter control. Rejection of the agency was not necessary: the windmill was now the Kennedys’ to turn and direct. They were determined to make it work under their close direction.173
CHAPTER TWO
THE CUBA PROJECT
“Everyone at CIA was surprised at Kennedy’s obsession with Fidel. There was no gung-ho [anti-Cuban] spirit among
the officers at the JM/WAVE station in Miami. They thought it was a waste of time. We all knew he [Fidel] couldn’t hurt us. Most of us at CIA initially liked Kennedy, but why go after this little guy? One thing is for sure: Kennedy wasn’t doing it out of national security concerns. It was a personal thing. The Kennedy family felt personally burnt by the Bay of Pigs and sought revenge. Papa Joe taught his sons well: ‘Don’t get mad, get even.’”
—Sam Halpern, CIA executive assistant to William Harvey and the Cuba Project1
Bobby Takes Charge
During the 1960 presidential campaign, candidate John F. Kennedy mused aloud, “There are two people I’d like to get out: Jimmy Hoffa and Castro.”2 And towards Castro, there was a certain, special level of ridicule. “Why doesn’t he take off those fatigues? Doesn’t he know the war is over?” In the wake of his Bay of Pigs debacle, now-president Kennedy appointed his brother as de facto head of all intelligence operations, including those of the CIA. From the time he became President-elect, Kennedy had hinted at such a move. In November 1960, Kennedy asked CIA Director of Covert Operations Richard Bissell whether it would be “useful to have an individual executive to pull the whole Cuban situation together who would know precisely at all times what State, CIA, and the military were doing and who could answer questions directly?” Now JFK had determined that that man should be his most trusted advisor, and the best organization man he knew—his brother.3
