A Cuban conundrum


Two years ago, Cuban counterintelligence officers arrested Alan P. Gross, a U.S. Agency for International Development subcontractor, as he boarded a plane in Havana for the United States. Later convicted in a closed trial of crimes against the state for smuggling sophisticated telecommunications equipment into Cuba, Gross is serving a 15-year prison sentence. Obama administration officials have declared that relations with Cuba will remain frozen until Gross is released, but the administration has not been willing to take the aggressive steps necessary to win his freedom. Gross’ fate, like Cuba policy generally, is now being sacrificed to electoral politics in Florida.

Ironically, if Gross were a CIA officer, he would probably be free by now. In 2010, Washington traded 10 Russian “sleeper” agents for four Russians jailed in Moscow for spying for the West. In 1979, President Carter crafted an informal bargain in which Cuba released four CIA agents imprisoned since the 1960s, in exchange for clemency for four Puerto Rican nationalists convicted of attempting to assassinate U.S. government officials in the 1950s. The history of the Cold War is replete with such trades. The CIA takes care of its own.

But Gross did not work for the CIA. He worked — in his words, as a “trusting fool” — for a USAID contractor participating in a U.S. government-funded democracy-building program. He traveled several times to Cuba on a tourist visa carrying computers, cellphones and satellite communications technology for independent nongovernmental organizations and individuals in Cuba’s Jewish community.


The Cuban government regards USAID’s democracy-promotion program as subversive, geared to foment regime change. It arrested Gross, a bit player in this larger diplomatic drama, to send Washington the message that Cuba will not tolerate such actions. U.S. officials expected that once the Cubans had made their point, they would free Gross on humanitarian grounds. But that hasn’t happened. As Foreign Minister Bruno Rodriguez told the New York Times in September, any humanitarian release would have to be based on “reciprocity.”

By that, Havana means the release of the so-called Cuban Five — five intelligence officers dispatched to the United States in the 1990s to spy on militant anti-Castro groups in the Cuban American community and imprisoned here since 1998. Their prolonged incarceration is a cause celebre in Cuba, and one can only assume that Cuban security officials are just as intent on looking after their own as are intelligence agencies everywhere.

When Jimmy Carter traveled to Cuba in March, his hosts floated the idea of an informal swap modeled on the release of the CIA agents and Puerto Rican nationalists in 1979. Carter has publicly called for the release of both Gross and the Cuban Five, albeit without linking the cases.

Thus far, however, the Obama administration has been unwilling to even consider such an exchange because of the inflammatory politics of the Cuban Five case in Miami’s Cuban American community. When former New Mexico Gov. Bill Richardson went to Havana in September hoping to negotiate Gross’ release, the State Department gave him only a meager list of reciprocal U.S. actions to offer. The Cubans indignantly refused to let Richardson even meet with Gross.

If Obama’s political advisors think that refusing to trade the Cuban Five for Gross will insulate the president from political heat on the issue, they don’t know south Florida. Republicans are already referring to Gross as a “hostage” and excoriating Obama for not forcing Cuba (somehow) to release him. From a strictly political calculus, Obama would be better off securing Gross’ release and getting the issue off the electoral agenda.

But the real concern ought to be safeguarding Gross’ well-being by finding an expeditious path to win his freedom. At present, the administration has put itself in a Catch-22: It won’t take any further initiatives to improve relations while Gross remains in jail, but the poor state of relations with Cuba is the main obstacle to his release. Based on the lessons of previous prisoner releases and successful negotiations with Cuba, the administration needs to take a more proactive approach.


The first steps should be aimed at improving the poisonous bilateral atmosphere between the two countries. The administration should allow Rene Gonzalez, the one member of the Cuban Five who has completed his prison sentence, to return home rather than forcing him to stay in Florida on parole for three more years. Obama should also remove Cuba from the State Department’s list of state sponsors of terrorism, where it has remained since 1982 only as a vestige of Havana’s support for Latin American revolutionaries during the Cold War.

Then the diplomatic stage will be set for a serious dialogue with the Cubans about what steps each side can take toward the release of both Gross and the Cuban Five. As the main bargaining chip, the administration should be ready to revamp the program that landed Gross in prison in the first place, redefining it to foster genuine people-to-people linkages, not creation of potential internal opposition. Successfully negotiating Gross’ release would serve not only a laudable humanitarian purpose but a wider diplomatic one as well.

Henry Kissinger, ever the realist, understood that dealing effectively with Cuba would sometimes require Washington to take the lead. “It is better to deal straight with Castro,” he advised his aides before sending them to begin negotiations. “Behave chivalrously; do it like a big guy, not like a shyster.” If Obama wants to welcome Gross home before another anniversary of his arrest rolls around, he should follow Kissinger’s dictum.

William M. LeoGrande is dean of the School of Public Affairs at American University in Washington. Peter Kornbluh is a senior analyst at the National Security Archive at George Washington University. They are the coauthors of the forthcoming book, “Talking with Castro: The Untold History of Dialogue between the United States and Cuba.”