Cuban spies have a particular talent for getting people to spill secrets. That's a problem for Washington

Cuba lies more than 100 kilometres from the nearest slice of the continental United States, but it has managed to keep a close eye on what Uncle Sam is up to for a very long time.

That's because it has repeatedly been able to find high-flying American sources who are willing to spill U.S. secrets to Havana — for years, or even decades.

They include Ana Belén Montes, the U.S. Defence Intelligence Agency analyst who passed secret information on to her Cuban handlers from the mid-1980s through to the start of this century. Her spying days ended with an arrest days after the 9/11 attacks.

Then there's Walter Kendall Myers, the great-grandson of Alexander Graham Bell and former State Department employee, who spied for Cuba nearly twice that long and was arrested in his retirement years. Now 86 years old, he is serving a life sentence at a Colorado prison.

Most recently, U.S. officials announced charges against Victor Manuel Rocha, a former U.S. ambassador and one-time member of the Bill Clinton-era National Security Council, accused of having acted as a covert agent for Cuba since 1981. The 73-year-old Rocha has pleaded not guilty to the charges.

Cuba has shown a knack for finding the right people to help advance its interests in the U.S. over the long-term. Yet former spy-catchers say the country remains undervalued in this realm, despite its prowess.

"They're not as big as the CIA but they've done a phenomenal job of punching the U.S. in the nose," said retired FBI special agent Pete Lapp, who helped investigate the spying activities of Belén Montes early in his career. His recently published book Queen of Cuba: An FBI Agent's Insider Account of the Spy Who Evaded Detection for 17 Years tells that story.

Eric O'Neill, a former FBI counter-terrorism and counter-intelligence operative, offered a similar assessment of Cuba's record on U.S. soil.

"They have been eating our lunch," he said in a recent interview.

Finding the right prospects

Spies have varied reasons for doing what they do.

Money can be a motivator. Infamous American spies Aldrich Ames and Robert Hanssen each got seven-figure payouts for their own espionage work for a different benefactor — Russia and the former Soviet Union.

But Lapp sees a difference in the prominent spies that Havana has worked with.

Belén Montes, for instance, didn't take money for her work for Cuba. Lapp said both she and Myers were motivated by ideology.

"The Cubans find these people that have a visceral empathy [for the cause]," said Lapp, noting they also look for people of a certain level of character, who are willing to take risks for Havana.

Gerardo Hernández, a once-jailed Cuban spy who was returned to Havana in a high-profile prisoner swap with the U.S., provided a glimpse of these professionals' thinking on the issue of paid spying in the 2020 documentary Castro's Spies.

"If you are a spy for money, then you will spy for the country that pays you the most," said Hernández.

At present, the Cuban state is grappling with an economic crisis, leaving its people coping with rising prices, shortages of key goods and a falling currency. These challenges have driven hundreds of thousands to leave their home country and head for the U.S. in recent years.

Far from Havana

The presence of Cuban spies in Canada has surfaced from time to time.

A January 1977 snowstorm briefly delayed the expulsion of five Cubans, who The Canadian Press reported were "ordered out … after discovery of a Cuban spy operation in Montreal."

In June 1988, a leaked letter outlining complaints CSIS agents had about staffing cuts in Montreal — where personnel from a Cuban airline and the consulate were apparently under surveillance — made its way to media outlets. The RCMP later raided several newsrooms, trying to determine who was responsible for the leak, according to reporting by The Globe and Mail later that year.

In the spring of 1995, Ottawa expelled several Cuban diplomats over allegations of spying. The Globe and Mail reported they were allegedly "trying to recruit informants and stir up political trouble in the Cuban exile community."

Five years later, a Cuban diplomat accused of being a spy caused drama when he was booted from the U.S. and then lobbed a curve ball during his carefully arranged return to Havana.

José Imperatori was headed home via an intermediate flight to Montreal when he unexpectedly travelled to Ottawa and stayed at the Cuban embassy for five days as he fought to return to the U.S.

The RCMP would end up escorting Imperatori's ride to the airport when he finally left the capital.

When Imperatori returned to Cuba, he was greeted by Fidel Castro.

Castro had previously admitted to "sometimes" sending spies state-side, and offered a justification for doing so.

"I think we have the right to do this," he told CNN in 1998. "The United States has spies in industrial quantities."

Sharp skills, undulled hostilities

Cuba's well-documented tensions with the United States date back decades. They remain today.

Given this political backdrop, U.S. authorities will want to uncover everything they can about what Havana may have allegedly gleaned from Rocha.

"That damage assessment is incredibly important to them," said Lapp, who believes it would be in the U.S. government's interest to reach a plea deal "because there's so much to learn."

The criminal complaint filed against Rocha describes an investigative effort by the FBI using an undercover agent, WhatsApp messaging and two in-person meetings — one at a church and another at an outdoor food court — to get him to speak about his alleged work for the Cuban government.

Authorities claim Rocha admitted to working as an intelligence agent in this capacity for "decades" and describing his work as "a grand slam."

A trial date has been set for Rocha next month. His lawyer, Jacqueline Arango, declined to comment on his case.