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Retired Jacksonville Diplomat: Cuba Prisoner Swap Just 'The Beginning'

Caulfield speaking
United States Interests Section Havana

More elected officials are condemning President Obama’s decision to release Cuban prisoners in exchange for American contractor Alan Gross. Among the latest voices of opposition is Northeast Florida Congressman Ander Crenshaw (R-FL4). But others are cautiously optimistic about what could lead to better relations between the two countries.

Longtime diplomat John Caulfield headed the U.S. mission in Havana, Cuba, until last year, when he retired to Jacksonville. In Cuba, Caulfield says he saw firsthand the struggle of imprisoned contractor Alan Gross.

“One of the things I did every month in Havana was visit Alan Gross in jail,” he says. 

Caulfield calls Obama’s decision, to trade three imprisoned Cuban spies for Gross, a difficult one. And he adds, it remains to be seen how deep and permanent the thaw in relations will be—and whether the aging communist regime is really improving its human rights record.

“This is a story that will evolve," Caulfield says. "It’s not the end of the story; it’s really the beginning.”

Caulfield says he’s seen somewhat of a softening in how Cuba treats dissidents. Crimes that used to get someone life in prison are now punished with a couple of days in jail and a beating, he says.