The Cuban Knot

The Vatican's Strategy in Havana

Cuba's Catholic Church leader Cardinal Jaime Ortega takes part in the annual procession of Our Lady of Charity, the patron saint of Cuba in Havana, September 8, 2014. Enrique De La Osa / Courtesy Reuters

The restoration of U.S.-Cuban diplomatic ties in mid-December demonstrated the geopolitical relevance of religious institutions. The deal would not have happened without the Catholic Church and Jewish organizations. Jewish groups made Alan Gross, the prisoner at the heart of the reversal, impossible to ignore; and then the Catholic hierarchy provided the trust required to move the negotiations beyond stalemate. U.S. President Barack Obama and Cuban President Raul Castro will surely benefit from the thaw in different ways, but anti-Castro Catholics resent the Church’s involvement.


Alan Gross was a USAID contractor who specialized in setting up Internet access. His work had been part of a big shift in the United States’ democracy promotion efforts on the island away from traditional political activism. A major setback occurred in 2003, when Cuba jailed some 75 democratic dissidents who had been associated with U.S. programs, which effectively shut down one of the most promising local opposition efforts since 1959. By 2009, the United States had turned toward more technology-driven programs (including a secret social media platform) and engaging marginalized communities.

It was under these circumstances that Alan Gross traveled to Cuba on tourist visas five times in 2009. His assignment from USAID (for which he earned $500,000 and a $3.2 million settlement) was to set up satellite Internet service for three Jewish communities. An estimated 14,000 Jews fled Cuba after the revolution, leaving behind a community of some 1,500 believers, which attracts wide support from around the world. For his USAID assignment, Gross identified himself as part of a Jewish humanitarian group and gave other American Jews some of his equipment to transport in carry-on bags, according to an AP review of his reports. 

Cuban security arrested Gross in December 2009, sending a strong message to the U.S. government and collecting a bargaining chip to help in negotiations over Cuba’s biggest grievance with Washington: the 1998 arrest in Miami of the “Cuban Five,” spies convicted of contributing to the deaths of four Americans. It is likely that Gross

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