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There's little sign the US or Cuba knows who's attacked US diplomats on the island, but there are worries hardliners are exploiting the situation.
Trump's efforts to further isolate the Cuban government and bolster the island's private businesses may have the opposite effect.
At least one Florida Republican is trying to wring concessions on Cuba from Trump over the GOP healthcare bill.
The US and Cuba have been negotiating for months to implement the change.
"So it's not sure exactly what Raul is going to do, but he's got to do something," said an American demographer.
Cuba appears to be in a historical moment following Fidel Castro's death. I traveled to Cuba two weeks after. It was not what I expected.
If it comes down to who Trump listens to, then the US's Cuba relationship may be about to see a major shift.
"Soon I'll be like all the rest," the 90-year-old former Cuban leader said. "Everyone's turn comes."
"El real Pánfilo. So nice to meet you," Obama said during his appearance.