How Cuba’s Spies Keep Winning

The failed landing on a rugged stretch of Venezuelan coastline last week by a band of mercenaries hoping to unseat Venezuelan dictator Nicolás Maduro is another tragedy for the beleaguered nation.

The predawn mission was meant to capitalize on the element of surprise. But the irregular soldiers were immediately confronted by Venezuelan troops because their operation had been thoroughly penetrated by Cuban-backed Venezuelan intelligence. Some were killed in the fighting and more may have been executed. Among the captured are two Americans.

The debacle is demoralizing for an enslaved nation suffering dire privation and brutal repression. It is also an opportunity to reflect on Cuba’s asymmetric-warfare capabilities and the sophistication of its intelligence apparatus, which over more than a half-century has run circles around the U.S. Beyond the killing, the fiasco will deepen suspicion and distrust among the members of the opposition-particularly of “friends” who claim to have broken with the dictatorship.

The U.S. government has said it had no “direct involvement” in the seaborne operation. Jordan Goudreau, a former Green Beret who was the ring leader of the plot, did receive some interest in his services from advisers to U.S.-backed interim Venezuelan President Juan Guaidó. But Mr. Guaidó’s communications team has put out a statement insisting that the interim president never agreed to launching the operation.

Mr. Goudreau, who heads the U.S.-based security firm Silvercorp, apparently planned to provoke a military uprising, detain Mr. Maduro, and put him on a plane to the U.S.

There is near universal agreement that it was a reckless endeavor. Yet it is only the latest in a string of desperate attempts to try to bring down the dictatorship. And while the methods have varied, the common denominator in all the quashed uprisings has been how effectively Cuban-led intelligence has disrupted the plans. In some cases the plots may even have originated with state-security agents, who recruited eager patriots and mercenaries and set them up to be killed. This also reinforces a sense of futility among would-be rebels.

Whether it’s inside the military or among the ranks of the opposition, many Venezuelans now conclude that Cuban moles are everywhere and it’s too risky to put confidence in anyone. This is key to Havana’s control strategy in Venezuela. It is also standard practice on the island.

The struggle to liberate Venezuela is a proxy war between the U.S. and Cuba, which is backed by its allies Russia, Iran and China. The conflict drags on because Cuba has the edge where it matters.

When it comes to traditional military capabilities, the U.S. soars above its adversaries. But Havana dominates in deception, human intelligence and propaganda. It’s been that way from the early days of the Cuban dictatorship. “The Cubans were underestimated for more than a quarter of a century,” former CIA Cuba analyst Brian Latell wrote in his 2012 book, “Castro’s Secrets.” The U.S. thought it was dealing with “bush-league amateurs” until Florentino Aspillaga Lombard, a highly decorated Cuban agent, defected in 1987. That’s when the U.S. began to understand that Castro’s Cuba had “developed a foreign intelligence service that quickly rose into the ranks of the half dozen best in the world.” Moreover, “in some covert specialties, particularly in running double agents and counterintelligence,” over decades, Mr. Latell wrote, “Cuba’s achievements have been unparalleled.”

It’s a mistake to think this is only about people like high-ranking Pentagon intelligence analyst Ana Belén Montes, who was exposed as a Cuban spy in 2001 after some 16 years working for the enemy. Cuba has myriad ways of spreading disinformation, combating critics, and widening its influence. Return access to the island for journalists and academics, for example, is denied when there is unfavorable coverage, which is presumably why yours truly cannot get a visa.

Blackmail is another method of manipulation. I have twice interviewed a Cuban defector who told me it was his job in Cuba to retrieve videocassettes from hidden cameras in hotel rooms and official residences where visiting dignitaries were staying. The goal was to capture on film compromising behavior that could be used to extort political favors or, for example, force a resignation. With heavy political and diplomatic traffic to the island from Europe and Washington, it’s a safe bet that at least a few have been compromised in this way.

The Guaidó team now says it balked at the Goudreau plan in part because it did not trust former Venezuelan General Cliver Alcalá, whose brother is Mr. Maduro’s ambassador to Tehran but who claimed to have switched sides. Mr. Alcalá was taken into custody in the U.S. on drug-trafficking charges in March. But that he got close to the Guaidó team in the first place is another credit to Cuba’s intel network-most likely in this case with a lot of help from Iran.