Despite a withered economic base, few exports of any value, and a repressive state bureaucracy, Cuba and the Castro regime have an outsized international presence. Recently, Havana appeared to be the international diplomatic broker for former U.S. intelligence analyst Edward Snowden’s asylum applications to various Latin American countries with a history of poor relations—and no extradition treaties—with the United States.

This July, Panamanian authorities seized a North Korean cargo vessel loaded with aging Cuban military equipment. Hidden under tons of Cuban sugar, the equipment was reportedly on its way to North Korea for refurbishment. This bizarre episode—an uncharacteristic misstep by the Cuban government—led to United Nations sanctions inspections and drew new attention to Cuba’s ongoing security relationships with pariah states like North Korea.

What explains the fact that, time and again for decades, the small, poor island nation manages to position itself at the fulcrum of superpower relations, especially within the Americas? At least part of the answer relates to a Cuban core competence: its aptitude for espionage. Cuban intelligence services are widely regarded as among the best in the world—a significant accomplishment, given the country’s meager financial and technological resources.

Earlier this year, Cuban leader Raul Castro announced his intention to step down in 2018—Cuba’s most significant political transition since the 1959 revolution. The government is also promoting major economic reforms aimed at spurring growth, attracting more foreign investment, and moving most of the labor force off of the government’s books and into Cuba’s fledgling private sector. Rumors abound that Havana and Washington are quietly discussing a path toward the lifting of the U.S. trade embargo. What would such liberalization mean for Cuba’s world-class spy agency?

The DI’s rich history

The Directorate of Intelligence (Dirección de Inteligencia,orDI, also known as G-2 and, earlier, as the Dirección General de Inteligencia, or DGI) is Cuba’s most important intelligence agency. It took shape under the tutelage of the Soviet KGB: Beginning in 1962, Cuban officers were trained in Moscow, and from 1970 onward, KGB advisors worked intimately with Cuban intelligence officials in Havana. By 1968, according to a declassified CIA report, the DGI had been “molded into a highly professional intelligence organization along classic Soviet lines.”

The relationship was symbiotic. For Cuba’s leadership, the U.S.-led Bay of Pigs invasion of 1961, coupled with numerous CIA plots to assassinate Fidel Castro, cemented America’s position as the revolution’s deadliest enemy. The Soviet Union’s intelligence services—paramount in the communist world—were an obvious and welcome ally in the struggle against the United States and the West more generally.

The Soviet Union’s high confidence in its Cuban protégés was evident by the early 1970s, when the KGB delegated Western European intelligence-collection responsibilities to the Cubans following the mass expulsion of Soviet spies from London in 1971. Beginning in the mid-1970s, Cuban and Soviet services began the joint cultivation of targets in the U.S. Defense Department, the intelligence community, and U.S. military facilities in Spain and Latin America.

During the 1980s, Cuban intelligence had a substantial presence in El Salvador and Guatemala, where U.S.-backed regimes were fighting insurgencies. In Nicaragua, U.S.-supported Contra rebels were battling the leftist Sandinista government. Cuba’s intelligence presence in Western Europe was also substantial. The DI reportedly had 150 officers in Spain—considerably more than any NATO country had in the Spanish capital at the time. In addition to spying on NATO military forces, the DI was responsible for acquiring American technology denied to Cuba under the U.S. embargo.

The Cuban-Soviet espionage partnership was also evident at the massive electronic eavesdropping installation in Lourdes, near Havana. Construction began in the summer before the Cuban Missile Crisis in 1962. At its peak of operations, some 1,500 Soviet personnel worked there. Signals intelligence specialists intercepted U.S. telephone calls, computer data, and other communications throughout the 1960s and into the 1990s.

Portions of the intelligence “take” involving U.S. capabilities and intentions regarding Cuba were no doubt shared with the Castro government. The Russians shuttered Lourdes in December 2001—a casualty of fiber optics, the digital revolution, and Moscow’s unwillingness to continue making annual rent payments of $200 million to Cuba to keep the listening post open.

Cuba’s niche: human intelligence in the United States

The closure of the Lourdes facility made collection by other means—particularly through human sources—all the more critical. Cuba had long maintained spy networks inside the United States to infiltrate and monitor anti-Castro exile groups. From 1992 until the FBI arrested its members in 1998, the so-called Wasp Network (La Red Avispa) surveilled South Florida exile groups like Alpha 66, targeted the offices of Cuban-American politicians, and sought jobs at the U.S. military’s Southern Command headquarters in Doral, Florida.

Cuba launched other ambitious espionage operations. Cuban-born husband-and-wife spy team Carlos and Elsa Alvarez, employees of Florida International University, received coded instructions via shortwave radio and gathered information on Miami-area notables that the DI used to build “intelligence files on individuals of interest to it,” according to the U.S. Department of Justice. The couple, arrested in 2006, pled guilty and received relatively stiff sentences (even after cooperating with prosecutors). In 2010, another husband-and-wife spy team, Kendall and Gwendolyn Myers, pled guilty to espionage charges after thirty years of spying for Cuba. As a senior analyst at the State Department’s Bureau of Intelligence and Research, Kendall Myers had access to some of the intelligence community’s most secret and sensitive information. He received a life sentence.

By all accounts, these cases were relatively minor compared to the espionage committed by Ana Montes, a senior Defense Intelligence Agency analyst and a top U.S. government expert on Cuba. Arrested in 2001, Montes had spent the previous sixteen years passing highly classified information to her DI handlers—including the names of U.S. agents in Cuba. Cuban intelligence recruited Montes after allegedly being “talent-spotted” by Marta Rita Velazquez, who at the time was serving with the U.S. Agency for International Development. (Last April, U.S. officials unsealed an espionage indictment against Velazquez, who now reportedly lives in Sweden.)

Like the Myers and Alvarez couples, Montes received instructions by encrypted messages sent by shortwave radio, a relatively simple but secure form of communication and a testament to the Cuban service’s tried-and-true spy tradecraft. Like the Myerses, Montes was an ideological traitor motivated by a fervent commitment to the Cuban revolution. Montes is now serving a twenty-five year term in federal prison.

Havana’s deep reach into Caracas

The DI has played an important part in the relationship between Cuba and Venezuela, the Castro government’s closest ally. President Hugo Chávez was ideologically (and personally) mesmerized by the charismatic Fidel Castro and his revolution. Little wonder, then, that when Chávez felt himself surrounded by conspirators and traps in his first years in office—especially after the 2002 coup attempt (with the clumsy endorsement of the Bush administration)—he turned to Havana for help.

Venezuela proudly touts its close relations with Cuba. In 2007, Chávez announced that more than twenty thousand Cuban doctors, nurses, and technicians were providing health services in the country. In 2005, sources estimated that the total number of Cubans working in Venezuela was approximately forty thousand, though several thousand were reported later to have fled abroad. According to the Venezuelan government, Cubans provide a range of expertise including medical care, sports training, infrastructural engineering, telecommunications, and the organization and training of “Bolivarian” community militias prepared to stave off a U.S. invasion. Cuba’s advisory presence has also included large numbers of DI officers.

Venezuela’s critics (including a few former high-level officials in the Chávez government) allege that Cuba’s influence is far greater and particularly strong within the government’s intelligence agencies. According to press reports describing a 2006 U.S. State Department cable obtained by WikiLeaks, Cuban intelligence advisors had direct access to Chávez and ultimate oversight over some of the intelligence he received. According to the cable, Venezuela’s intelligence agency displayed the requisite revolutionary élan in its anti-Americanism, but lacked the expertise of its Cuban partners. The DI went on to restructure and retrain the Bolivarian Intelligence Agency in Cuban methods, particularly the penetration, monitoring and exploitation of political opposition groups.

Documents have also described high-level political machinations by senior DI officers in Caracas—notably, that the service appeared to have orchestrated various turnovers within Chávez’s cabinet, as the DI officials sought to promote more ideologically rigid party loyalists over military officers. The Venezuelan military is the only state institution that resisted the government’s deepening and widening reliance on Cuban advisors; such resistance weakened over time as outspoken critics were purged from the armed forces.

Under Chávez’s successor, Nicolás Maduro, Cuba’s intelligence reach within Venezuela seems only to have increased. The entourage traveling with Maduro to New York for this year’s UN General Assembly included Cuban intelligence officers, according ABC, a Madrid daily. The paper claimed that Maduro’s plane was forced to return to Caracas after the United States denied visas to the Cubans on board. The leak of a recorded phone conversation between Mario Silva, a senior socialist party loyalist and TV personality, and a DI officer caused a major scandal. In the phone call, the loyal chavista laments to the Cuban about the corruption, incompetence, and infighting among the Maduro government’s top officials. The Venezuelan media have also called attention to the Maduro government’s contract with a Cuban state-owned company to administer Venezuela’s database of its residents and their foreign travel, and to produce national identification cards that will include biometric information. According to published reports, Argentina and Bolivia have also invited Cuba’s services to help create new national databases and identification cards.