Obama's Very Sly Cuban Move

For years, President Barack Obama faced a tough problem: what to do about Alan Gross, the US subcontractor imprisoned in Cuba? And this dilemma encapsulated the larger puzzle of how to change US-Cuba relations, which have been frozen in a Cold War narrative.

The Cubans arrested Gross in 2009 and threw him in jail for distributing internet communications equipment under a program funded by the US Agency for International Development. The Cubans claimed he was a spy helping dissidents set up a secret communications system; the Obama administration insisted he was no such thing and was merely promoting free expression within Cuba's Jewish community. After Gross, who was in poor health, was sentenced to 15 years in prison, the Cubans offered the Americans a deal: They would free Gross if the United States released the Cuban Five, five Cubans arrested for spying in 1998 in Florida and later convicted and given long prison sentences. (One of the five was paroled in 2011; another comes up for parole in February.)