In 1982, Cuban counterintelligence photographed Richard Brennan, a secretary in the political-economic department of the US Interests Section in Havana, placing a package in tall grass next to a road sign outside the city.

It was a dead drop. Inside the package were 25,000 Cuban pesos, one-time pads for encrypted communication, an RS-804 covert communications device, and other highly incriminating materials.

Brennan would repeat this operation more than a dozen times between 1982 and 1984, each time accompanied by his wife Virginia, a common practice among CIA case officers operating in hostile territory where a couple draws far less suspicion than a lone operative.

The fact that Cuban intelligence was watching was no accident.

From the earliest days of Fidel Castro’s government, the Intelligence Directorate had been quietly building one of the most effective counterintelligence operations in the Western Hemisphere, infiltrating anti-communist groups, intercepting smuggled arms shipments, and monitoring American personnel on the island.

By the 1980s, conducting CIA operations in Cuba had become extraordinarily difficult.

The full picture came into focus in June 1987, when Cuban agent Florentino Aspillaga defected to the United States and revealed that at least 27 CIA-run agents inside Cuba had been turned against the agency.

The following month, Cuban state television released a documentary naming four American diplomats as suspected CIA officers and claimed that since 1977, 38 out of 69 personnel assigned to the US Interests Section in Havana had actually been working for the CIA.

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