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Kennedy's compulsive womanizing is of consequence not only for what it says about his character but also because it could have made him vulnerable to blackmail. Hersh suggests that it did, but never produces convincing proof. Why did Kennedy name Johnson as his running mate, despite Robert Kennedy's distaste for Johnson? Many historians have concluded that it was pure political calculation: Johnson could deliver Texas. Hersh thinks it was blackmail. He says that during a closed-door meeting with Kennedy, Johnson may have threatened to disclose J.F.K.'s dirty laundry, though Hersh doesn't know which laundry or even whether Johnson had anything on Kennedy at all. His main source? The late Hyman Raskin, a little-known Chicago lawyer and Democratic political operative. In interviews and an unpublished memoir, Raskin says that Kennedy had settled on Missouri Senator Stuart Symington as his running mate until Johnson and Speaker of the House Sam Rayburn pulled him into that mysterious meeting.
Raskin's claim is seconded by Clark Clifford, the longtime Washington power broker, who tells Hersh he served as Kennedy's go-between with Symington. Later, says Clifford, Kennedy told him he was forced to accept Johnson. But blackmail is a badly stretched conclusion for an author who has so little hard evidence to go on--and who paints Johnson in other parts of the book as ignorant of Kennedy's hidden undertakings.
When Hersh takes on Kennedy's foreign policy, he runs into the same kind of problems. Kennedy loyalists argue that J.F.K. was no more than an interested bystander in the CIA campaign to murder Castro. But during the failed Bay of Pigs invasion, Hersh writes, Kennedy was in fact expecting that Castro would be quickly assassinated by Giancana's men. His fateful decision to abandon the whole thing was the abrupt consequence of his getting the news that the Cuban leader was still alive.
It has long been known that some of the invasion planners were plotting to have Castro killed. "Assassination was intended to reinforce the plan," as the late CIA official Richard Bissell coolly put it in a 1984 article in the quarterly Diplomatic History. Was Kennedy one of the planners who were in on the murder plot? Perhaps, but to be sure of that, it helps to be persuaded by Hersh's attempts earlier in the book to prove that Kennedy "must have" been in communication with Giancana--or at least that he was briefed before the 1960 election by Bissell or CIA Director Allen Dulles about the covert operations in Cuba approved by Dwight Eisenhower. Like Richard Nixon, Hersh believes Kennedy must have been, but Dark Side never proves it.
Hersh argues that the Kennedy brothers were the U.S. government's "strongest advocates" of CIA plans to kill Castro, not merely dispassionate judges of tough-guy talk from the spy shop. After the Bay of Pigs, Hersh writes, "the necessity of Castro's death became a presidential obsession." Former CIA Director Richard Helms told much the same story in 1975 to the Church committee, the Senate body investigating CIA shenanigans. Samuel Halpern, onetime executive officer of the CIA's Task Force W, an enterprise charged with the single mission of killing Castro, says the Kennedy brothers wanted Castro dead "for personal reasons--because the family name was besmirched by the Bay of Pigs."