On the one hand, Obama's overtures towards Cuba are not a complete surprise. If you recall back in early 2008, John McCain was bashing Barack Obama for taking a soft stance on Cuba by promising to engage Cuba. In so doing, John McCain tried to cater to Florida's Cuban American population by promising not to engage with Cuba unless a long series of preconditions were met.
However, consider the timing and choreagraphy of Obama's recent outreach towards Cuba, as well as how Obama managed to turn the issue of Cuba's absense from the Summit of the Americas into an advantage of the Summit. By taking steps towards engaging Cuba just as other countries were planning to demonize the U.S. for its hypocritcal hardline on Cuba, President Obama put other nations in a put up or shut up mode. The Latin American countries were planning to make a big stink about Cuba's absense from the Summit. Hugo Chavez had already previously dissed President Obama much earlier. However, by making some outeach toward Cuba, the other countries, including Cuba had to put up or shut up.
In other words, if Cuba then rejected President Obama's offers of engagement, then Cuba, not the U.S., would then look like the bad guy for insisting on remaining isolated from the United States. Likewise, Hugo Chavez who made a living on blasting the U.S. for refusing to acknowledge Cuba, would also look foolish if he denounced or rejected the U.S.'s outreach towards Cuba. Cuba and Venezuela would have looked liked the isolationists, not the United States.
So, there's a new administration in the White House. Rather than get played on Cuba, the United States stole the initiative, and forced other countries to put up or shut up by taking the wind out of the anti-American rhetoric. I had almost forgotten what it was like for the United States to have diplomatic juice, rather than resorting to blunt threats of force.
http://www.nytimes.com/2009/04/18/world/americas/18prexy.html?hp/snip
Other leaders here said that in watching Mr. Obama extend his hand to Cuba, they felt they were witnessing a historic shift. And in another twist, Cuba’s strongest ally at the summit, President Hugo Chávez of Venezuela, no fan of the United States, was photographed at the meeting giving Mr. Obama a hearty handclasp and a broad smile.
Cuba is not on the official agenda here; indeed, Cuba, which has been barred from the Organization of American States since 1962, is not even on the guest list. But leaders in the hemisphere have spent months planning to make Cuba an issue here.
The White House was well aware that if Mr. Obama did not address it head on, the issue would overwhelm the rest of the summit gathering. This week, the president opened the door to the discussions by abandoning longstanding restrictions on the ability of Cuban-Americans to travel freely to the island and send money to relatives there./snip