A Brief History of Lee Harvey Oswald’s Connection to Cuba

For over 50 years, conspiracy theorists have linked JFK’s assassin to Fidel Castro’s Cuba

August 16, 1963 - Lee Harvey Oswald passing out Fair Play for Cuba leaflets in New Orleans

Donald Trump raised eyebrows this week when he alleged that the father of his former rival in the Republican presidential primaries once had links to Lee Harvey Oswald. The claim, which came just hours before Republican presidential candidate Ted Cruz dropped out of the election, stemmed from a recent story in the National Enquirer suggesting that Cruz's father, Rafael, can be seen in a photo of Oswald and several pro-Cuba activists several months before the assassination of President John F. Kennedy.

The allegations were summarily dismissed by the Cruz campaign, and the Miami Herald’s Maria Recio points out several gaping holes in the theory shared by the real estate mogul and the supermarket tabloid. But while these unsubstantiated claims might seem like just another surreal beat in this odd election year, like any good conspiracy theory, the story relies on real history, in this case the decades-old argument that there was a deep connection between the presidential assassin and Communist Cuba.

In many ways, Fidel Castro’s Cuba was one of Kennedy’s greatest nemeses during his tenure as president. From the failed Bay of Pigs Invasion to the Cuban Missile Crisis, the small island nation played a central role in Kennedy’s foreign policy. After all, having a Communist country within spitting distance of the United States was a persistent bugbear of Kennedy’s short-lived presidency, David Corn writes for Mother Jones. In addition to these public efforts, Kennedy was also waging a secret war against Castro, with the CIA developing all sorts of plans to try and kill the Communist leader (a choice few involved an exploding seashell and a poison-spewing pen).

Cuba and Castro’s politics also played an outsized role in Oswald’s life, but in a very different way. While Kennedy strived to take the dictator down, Oswald spent years advocating on behalf of Castro and his Communist regime in the United States. At one point, Oswald reportedly applied for passage to Cuba at its embassy in Mexico City, but was allegedly rejected because the government feared he was an undercover provocateur. The photo that resurfaced on the National Enquirer’s cover in April was taken three months before Oswald assassinated Kennedy, when he and a pair of hired hands were passing out pamphlets on behalf of a pro-Castro organization called the "Fair Play for Cuba Committee," Philip Bump reports for the Washington Post.

With this in mind, it wasn’t too much of a leap at the time to suppose that Kennedy could have been the target of a Cuban-led conspiracy with Castro at the head. In fact, even Castro himself understood how easily it would be for him to be blamed for the president’s death – and he had good reason to fear that conclusion. If investigators determined that Castro had been behind the killing in any way, that could be considered an act of war and grounds for an American invasion of Cuba, Jeffrey Goldberg writes for the Atlantic. Castro went so far as to secretly meet with a member of the Warren Commission that investigated the circumstances around Kennedy’s death on a yacht off of Cuba’s coast in order to convince American officials that he had nothing to do with Oswald.

Ironically, Castro himself has said he believes Kennedy was assassinated for his actions towards Cuba. During a 2013 interview, Castro told Goldberg that he believes in several popular conspiracy theories about Kennedy’s death, including that there were multiple shooters and that Oswald may have acted on behalf of members of the American government.

The events may have lined up to suggest a narrative where Oswald killed Kennedy because of his anti-Cuba policies, but it seems incredibly unlikely that Rafael Cruz (a Cuban refugee and avowed anti-Castro activist) would have had anything to do with the pro-Castro Oswald.

Today, 53 years after the fact, it remains impossible to do anything but speculate on Oswald’s intentions. And in the absence of evidence, all manner of wild-eyed theories continue to easily take root.

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