Fifty-four years ago, one of the most suspicion-wracked and contentious international relationships (next to the U.S.’s with the Soviet Union) heated up when the United States and Cuba ended formal diplomatic ties and closed their embassies in Havana and Washington D.C., respectively.

The years following the break were marked by accusations of sabotage and attempted assassinations, proxy wars, and nuclear near-misses. That icy tension thawed a bit on Monday, July 20, 2015, if not completely, as both nations have opened their embassies once again. This news comes on the heels of renewed diplomatic talks and the lifting of embargoes and a decades-long travel ban.

The diplomatic dance has begun anew, and for those in the intelligence community, there are sure to be mixed feelings. Although access to the country has eased, lingering questions, concerns, and doubts, given our history, likely remain.

So after almost 55 years of trying to penetrate the inner workings of the tiny island that has proved to be a big policymaker nightmare, how might past events stack up for or against future U.S. intelligence operations in the region?

FILE - This Dec. 17, 2014 file photo shows a classic American car driving past the U.S. Interests Section buidling in Havana, Cuba. A half-century after Washington severed relations with Cuba, the seven-story mission is set to become a full-fledged embassy. The U.S. and Cuba announced on Dec. 17, 2014 they are re-establishing full diplomatic relations. (AP Photo/Desmond Boylan, File)
(Photo courtesy of AP/Desmond Boylan)

In the mid-1950s, Cuba began a relationship with the Soviet Union, creating an instant political rift with the United States, who to that point had enjoyed a cordial relationship with her tiny Caribbean neighbor. Havana had been the playground of many a famous name, from Ernest Hemingway (whose name now graces the ballroom in the Cuban former consulate/new-again embassy) to Hunter S. Thompson.

With her vintage cars, nightclubs and Spanish-style architecture, Cuba had long been a favored trek for movie star and spy, from British, to German, to the fledgling CIA. All of that changed in 1959, when a young communist revolutionary named Fidel Castro launched a successful and bloody coup that landed the island nation firmly in the USSR’s camp, and effectively closed the door to outside influence and observation.

For the CIA, outside of Moscow, Havana quickly became an intelligence focal point. Policymakers, most notably the Kennedy administration, wanted to know what was going on the island, and most importantly, what the Soviets had planned for their newfound little brother. Traditional HUMINT (human intelligence), while not yet to the “impossible” point, was proving more difficult as Castro’s forces rolled up both real and suspected agents, quickly imprisoning or executing them.

Some with anti-Castro leanings had fled the island in the initial stages of the revolution, but communications with those left behind needed to form a resistance army, if any, were scarce and soon, nonexistent. If the Castro regime was to be effectively resisted and hopefully toppled, the Agency would need to flex its covert action/covert influence muscle.

According to, by 1960, a plan was already in the works to counter Castro. A working group called the 5412 Committee convened and released a paper on March 16, 1960, titled “A Program of Covert Action Against the Castro Regime,” which outlined a broad plan that sought to “bring about the replacement of the Castro regime with one more devoted to the true interests of the Cuban people and more acceptable to the U.S., in such a manner as to avoid any appearance of U.S. intervention.”

Methods that the paper proposed included the creation of a covert intelligence and action organization in Cuba that would take its orders from the anti-Castro opposition via a long- and short-wave gray broadcasting facility to be located on Swan Island (a chain of three tiny islands located in the northwestern Caribbean Sea, approximately 110 miles north off the coastline of Honduras) and a cadre of leaders to be screened and trained as paramilitary instructors for the purpose of raising and training a resistance force.


As best laid plans go…well, all plans bump into the infamous Mr. Murphy at some point in time. In this case, Murphy met and stomped a mud hole in the plans for the Bay of Pigs Invasion. You know how the rest went.

That wasn’t the only major setback that the U.S. intelligence community was handed, compliments of the Cubans. In September 2001, just 10 days after the attacks on the World Trade Center, the Pentagon, and Pennsylvania, the FBI arrested a woman named Anna Montes. Montes had a been a senior intelligence analyst with the Defense Intelligence Agency, the DoD’s baby. She had met with two Cuban officials in 1984 while in a clerical position at the Department of Justice, after they had taken note of her vocal criticism of U.S. foreign policy in Central America.

By the time of the 9/11 attacks, Montes was well entrenched at DIA and able to not only steal secrets, but also purposely distort U.S. policymakers’ views of the situation in Latin America. Her arrest stopped the hemorrhage of classified material, but along with the arrests of Aldrich Ames and Robert Hansen, became an intelligence embarrassment as well.

For years, it has been believed that of an undisclosed number of Cuban nationals recruited by the CIA to spy against the Castro regime, almost all of them were double agents directed at the Agency to spread disinformation and gain knowledge of other, actual agents working for the United States. If true, the damage to operations in the Latin America region were and may still be at significant risk, and while tourists flock to the warm weather, white beaches, and cigars, the U.S. military and intel community would do well to watch the happenings with a wary eye at arm’s distance.

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Former CIA case (operations) officer John MacGaffin captured the timeless sentiment exactly when he said, “No matter what has happened or what lies ahead, clandestine HUMINT will nonetheless remain the indispensable element of national intelligence collection.” He also goes on to say that HUMINT is appropriate when “no other option is available or has a real possibility to succeed.”

In this case, MacGaffin was speaking about the transformation of U.S. intelligence in the face of emerging technologies and non-state actors, but his words are more than appropriate in light of renewed diplomatic relations with Cuba and the “re-opening” of the island. Whether or not ops officers have been or ever will be working in Cuba again is open for speculation and not something for discussion here, but what is known is that Cuba has a proven track record against our intelligence agencies, and to let this recent thaw bring our guard down can and will leave us with a black eye in the southern hemisphere.

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