Spies like former US ambassador Victor Manuel Rocha and Ana Montes aren’t just stealing secrets for Cuba, they are helping Havana become an international broker of US intelligence - selling America’s secrets to the highest bidder.

The US considered Havana intelligence ‘lightweights’ until Cuban Major Florentino Aspillaga defected to America in ‘87. Aspillago, a high-ranking Cuban officer from the DGI intelligence service, revealed that the KGB-trained Cubans deliberately portrayed themselves as amateurs so they could operate discreetly.

"From New Year's Day in 1959, when Castro won power, until the summer of 1987, they were viewed as bush-league amateurs, Latino lightweights in the conspiratorial sweepstakes of superpower espionage,” Brian Latell, a retired CIA analyst, writes in Castro’s Secrets (2012). 

And that was exactly how the cunning Cubans wanted to be perceived - it allowed Havana to spy freely under the radar. Aspillaga’s defection was a game changer though. Up until that point, the Americans grossly underestimated the Cubans. “We never imagined that little Cuba could run an intelligence service that was world-class,” Latell said.

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Aspillaga: How Castro’s spymaster escaped 

Major Aspillaga, barely 40 when he defected, blew a hole in Castro’s strategy. Aspillaga was Cuba's Czechoslovakian intelligence chief in June 1987 when he drove an embassy car across the border from Bratislava into Austria and then introduced himself to US Embassy diplomats in Vienna.

This was the era of Soviet leader Mikhail Gorbachev's glasnost and perestroika, just a few years before the USSR collapsed.

Aspillaga was a high-level ‘walk-in’, an unexpected gift, and the Americans were all ears. He revealed that Fidel Castro’s seemingly impoverished island of sugarcane, sangria, and vintage Chevys was punching far above its weight in intelligence matters.

Reportedly, Cuba had been training officers in Moscow since the 1960s under the tutelage of the KGB secret police and had developed a sophisticated network. In interviews described by the Washington Post as “intensive debriefings”, Aspillaga told the CIA that nearly every spy the CIA had recruited in Cuba since the early 1960s was a double agent loyal to Castro. This had been the case since the Bay of Pigs debacle in 1961, he maintained.

Furthermore, in the three decades since Fidel Castro took power, Cuba’s intelligence service had reportedly fielded four dozen double agents in a world-class operation under the nose of the CIA, according to Brian Latell who interviewed Aspillaga over several days.

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Cuba’s expanding spying network

Not content with just stealing American secrets, Cuba began ‘trafficking’ US intelligence to American enemies in the years before the US invasion of Grenada in 1983, according to Chris Simmons, a former US Army officer, Defense Intelligence Agency analyst, and author of Castro’s Nemesis (2022).

What started as a way to inflict damage on the US developed into a more sophisticated system of trading American intelligence in exchange for favors or money. That might mean trading secrets for commodities like oil, money, political influence, or a seat at the table in negotiations, Simmons said.

Former FBI Special Agent Peter Lapp, the lead investigator on the Ana Montes Cuban spycatcher investigation and author of Queen of Cuba, doesn’t consider trading secrets to be ‘selling’ or ‘trafficking’, however.

“I think the Cubans bartered the intelligence they got from Montes, Marta Velazquez, Kendall Myers - and others yet to be identified - to use that for influence or a commodity. Maybe it’s oil, or maybe some kind of grain or something, but I wouldn’t say they ‘sell’ it.”

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Cuba’s intelligence revolution

Havana’s foreign intelligence services are still ranked among the half-dozen top agencies globally, according to intelligence experts. “They are pound-for-pound one of the best intelligence services in the world,” Lapp said.

So much so, Cuba has reportedly trained other nations on the best way to organize their intelligence services - much like during the Cold War when Moscow’s KGB helped train Havana’s DGI (later renamed the Direccion de Inteligencia).

According to a 2019 Reuters report, Venezuela’s Hugo Chavez turned to his close confidant, Fidel Castro in late 2007 for advice on how to update Venezuela’s intelligence services although neither country has acknowledged details of an agreement or Cuban involvement.

As for Major Florentino Aspillaga, he was targeted for assassination, as he feared, with the first attempt in London in 1988. When CIA analyst Brian Latell interviewed him, however, Aspillaga was living quietly as an American citizen with a new identity.