Magnets for sale decorate a tourist shop, one showing an image of U.S. President Barack Obama smelling a cigar, at a market in Havana, Cuba, March 16, 2015. (AP/Ramon Espinosa)
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Obama was not the first Democratic president to reach out to Cuba, but his attempt took advantage of – and carefully judged – a generational shift among Cuban-Americans that greatly reduced the political risks.Obama's people-to-people Cuba strategy was complicated by one person in particular: Alan Phillip Gross.The U.S. government had sent Gross, a USAID contractor, on risky missions to deliver communications equipment to Cuba's Jewish community. His December 2009 arrest put Obama's planned "new beginning" with Cuba on hold. Gilbert worked with the Obama administration, but urged it to move faster.Obama hammered home his opposition to a straight Gross-Cuban Three trade, two people present said.The pope did so, then wrote personal letters to Obama and Castro.Castro and Obama, whose Cuba policy still faces vocal opposition from anti-Castro lawmakers, will come face to face at next month's Western Hemisphere summit in Panama. Aides have dared to imagine that Obama could be the first U.S. president to visit Cuba since Calvin Coolidge in 1928 .
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