Conan almost looks like Caesar Flickerman on the streets of Havana. My wife is Cuban, I grew up in Miami. Cuba is a beautiful country with an interesting culture and a extremely corrupt oppressive government. The government of Cuba lies somewhere between Russia and North Korea for political oppression it is the type of place where expressing discontent the government in your own home can get you thrown in jail for years without judicial process. I do not have the words to describe the soul sucking disparity that exists in that country if you're not coming in with first world money.
My brother in Law was thrown in jail for a year just for trying to leave the country. He went into jail 200lbs and exited just over 110bs.
Please understand with some intellectual honesty that people will not risk their lives [1] and face jail time in the equivalent of a Russian gulag if things are peachy dory.
Cuban here, I also lived in Russia several months and my wife is Russian. Cuba is well below Russia (and of course North Corea) in terms of oppression. Marco Rubio never lived in Cuba and only reflects the feelings of the previous generation of Cuban that emigrated to Miami when Castro took the power. This is understandable as Castro took many of their properties but has nothing to do with how cubans from 2015 feel. This can be easily seen when you note that he spoke against the Cuba-US relationship improvement recently introduced by Obama which is clearly something most of cuban supported.
My wife lived in Cuba from when she was born up until 2005 when her grandmother was finally able to get a family reclamation to go through. She knows many who were thrown in jail just for being associated with people who the government was "unhappy with". I would agree it's not as bad as North Korea, maybe my opinion of Russia is too high.
I never knew anybody who went to jail for speaking against the government neither directly heard such a story but I can believe that happens(journalist Yoanis Sanchez is an example). This is the way I see it, the government normally don't care much about this people or what they think/say, except when they try to do something that could affect their public image, for example if the Pope comes to visit and they want to organize a public protest. In this circunstances they are preventively sent to jail, and afterwards released when the visitor is gone. It is often the case that real criminals present themselves as "politic prisoners", that adds much noise to the whole situation and usually gets exaggerated by the media in Miami. While this is not ok, in Russia people actually get killed in similar circumstances, while the main opposition leaders in Cuba are all alive.
It's a fantastic place to visit. Until know, the embargo was an added benefit. Not just because the country was preserved as a sort of open-air 60ies museum – it was also an great place to meet Americans: because of legal restrictions, all Americans on Cuba were self-selected awesome people.
http://teamcoco.com/cuba