Cuba is well-known for sugarcane rum and hand-rolled cigars - even JFK couldn't resist stocking up on 1,200 Petit Upmann Cubans before announcing the 1962 US trade embargo. What’s lesser known is that the island is home to an elite espionage network. As US-Cuban super-spy Ana Montes prepares to leave her Texas cell this week, SPYSCAPE meets a few of its most dangerous double agents, reveals how the Caribbean island built a world-class spy network capable of rattling the US, and hears the latest from CIA officers about Havana Syndrome.
The Cuban mole
In the covert world of running spies, Cuba punches above its weight. Case in point: Ana Montes, a Washington, D.C. Defense Intelligence Agency analyst and Havana’s mole for 17 years. She’s known as ‘America’s most dangerous female spy’ but Ana almost slipped away quietly before her capture as bureaucratic infighting engulfed the FBI, DIA, and NSA.
Cuban-born MiG fighter pilot Juan Pablo Roque boasted about being Richard Gere’s ‘double’. He swam through shark-infested waters to claim US asylum and bought a Rolex with money earned working for the FBI. What the Bureau didn’t know was JP was also on Cuba’s payroll, gathering intel on Miami’s Brothers to the Rescue pilots - four of whom died a day after JP fled. In his wake, JP left a jilted wife and a mystery.
To strangers, ex-CIA officer Frank Terpil was ‘Robert Hunter’ - a retired Australian living with his young Cuban wife in a bungalow overlooking Havana’s eastern beaches. It was a good cover, just believable enough to distract from the New Yorker’s Brooklyn accent and intimate knowledge of weapons and Mideast politics. Some in the CIA suspected Terpil had gone rogue, recruited by Cuba’s General Intelligence Directorate. But did the CIA ever really let him go?
It was a long shot when the FBI called in Robert Booth to investigate who’d been selling secrets to Havana. The case was cold. Booth was now retired - so was his chief suspect: Kendall Myers. The great-grandson of telephone inventor Alexander Graham Bell spent his days sailing his yacht. Kendall seemed untouchable until Booth offered Myers something he couldn’t refuse - a Cohiba cigar and a passcode.
The CIA considered Havana’s intelligence services 'bush league’ until Cuban Maj. Florentino Aspillaga defected in 1987. Aspillaga opened the Agency’s eyes. The island of sugarcane, sangria, and vintage Chevys is also home to a sophisticated, Soviet-trained intelligence service. Havana isn’t just stealing US secrets, they’re selling them to America’s worst enemies.
Two years after the US resumed diplomatic relations with Cuba, intelligence officers began experiencing strange neurological symptoms. Before long, the phenomenon was affecting US officials worldwide. Veteran CIA officer Marc Polymeropoulos was struck down during a 2017 Russia trip. He joins Russia expert John Sipher and Dr. James Giordano for a special True Spies podcast examining the mystery illness.
