Politico notes President Obama's adeptness (and clear enjoyment) at forcing dictators to face difficult questions, and Chris Sabatini comments further. Press conference are uncomfortable for dictators, who are unaccustomed to...press. Raúl Castro fumbled and looked foolish, forced to talk about political prisoners when he didn't want to. But this sort of stage means he can't hide. That's really part of what normalization is intended to foster.
Castro tried to get his mojo back by raising Obama's arm in triumph, but he got a limp wrist instead.
The greatest part about all this is how much Obama is enjoying messing with Raúl. He got the upper hand, so to speak.
Under our decades-long punitive policy, there was no way to force this sort of situation. Fidel and Raúl could easily ignore everything U.S. presidents said, and never got tough questions. Now they no longer have that luxury.