administration had been sending out peace-feelers to Castro through back-channel diplomacy, to the great alarm of Washington national security hard-liners. While it was possible Castro wanted JFK dead, it seemed much more likely that he would know such a situation would be used against him, eventually as a rationale to end his own life and leadership in Cuba.
The issue had another level, however. In order to appease his hard-liners long enough to have a chance at making an accommodation over Cuba, the President had approved continuing a plan known as “Operation Mongoose.” It was aimed at de-stabilizing the Castro regime by any covert means necessary. There was no doubt that from a Cuban perspective, the U.S. was sending some mixed signals out of the White House.
Bobby eventually ended this debate saying “I’ll give this one top priority.” The President admonished him with a dry smile, “Not so fast, Bobby. We’re just getting started.”
Organized Crime
If the Kennedys had a challenging relationship with Cuba, they had no less of one with the powers of the United States Mafia. Despite — or perhaps because of — the common knowledge that family patriarch Joseph Kennedy had accumulated much of his wealth through illegal activity during Prohibition, Bobby Kennedy had chosen, in the late 1950s, to plant his personal and political flag square in the midst of the organized crime issue. He’d made his national debut as chief counsel for the Senate Labor Rackets Committee, squaring off mano-a-mano on national TV against Teamsters Union president Jimmy Hoffa and other highly placed mob figures. He’d also written a 1960 best-seller, The Enemy Within , that attacked organized crime as a greater threat to America than communism.
Indeed, as attorney general, Robert Kennedy had told his fellow crusaders at the Justice Department that failure was no option — they had to crush the mob or the mob would run the country.
That antagonistic relationship alone made a mob hit a real possibility. Yet the thinking went that if the Mafia wanted to kill a Kennedy, they’d probably go for Bobby first. After all, the Mafia godfathers had expected leniency from the Kennedy administration after their cozy friendship with Joe Kennedy, but instead they were the target of a declaration of war by his children, particularly Bobby.
Still, as with all the suspects, there were twists and turns that made thinking about the mob far more complex than could be seen at first blush.
There was the fact that Joseph Kennedy had convinced some organized crime members to help out with John Kennedy’s 1960 election, despite the fact that Robert's recent efforts to put them out of business were starting to border on obsession.
The greatest twist was that leaders of organized crime had been working hand-in-glove with members of U.S. intelligence to assassinate Castro in a classic “enemy-of-my-enemy” operation.
When President Kennedy excused himself to take a phone call, Bobby took the opportunity to alert the others to a “sensitive situation.” JFK had, from 1960 through 1962, an affair with the Los Angeles socialite Judith Campbell, who was also involved with Chicago mob boss Sam Giancana. Kennedy had used Campbell (later known as Judith Campbell Exner, after her 1975 marriage to professional golfer Dan Exner) as a messenger to communicate with Giancana, hoping to enlist support for the assassination attempts against Castro. Now the question was whether the mobster’s jealousy prompted him to try to rub out the President.
Bobby reminded the group of the need for discretion in this matter and stated that the only reason Campbell was even relevant to today’s conversation was her connection to Giancana. In other words, anything else in the area of “relationships” was none of the group’s business.
Before the President returned, the attorney general had another “priority” on his list to go along with the entire Cuban