The last time a sitting u. S. President stepped foot in cuba 1928 when Calvin Coolidge sailed there on a battleship from florida. They landed in havana a tonight. Remember 15 a months ago, the president announced decades long freeze was ending. The president s agenda is part business. Part diplomacy and part outreach. He will meet with dissidents, people who oppose the castro regime and this visit sets the tone for the two countries new future together. Chris cuomo is live in a rainy but what a night in havana. When you are talking to the people there, what are they saying about what this means for them . Theres anxiety and a mix and thats not unusual. That is what this is. Cuba has a lot of history. A lot of star dust for periods of the revolution. At the end of the day it is an oppress arive regime. At the end of the day cuba remains a third world country. People here, not just they dont have freedom of travel to the United States, they dont have Running Water on a regular basis, no power grid here. The internet is more of a myth than a reality. When you have these wifi hot spots they set up, people rush to them like they were looking for oxygen. Even when they get the internet theres a fear can they read and say what they want . The streets, yes, theres a ton of rain going on right now. But theres another reason the streets maybe empty. Theres no motivation for the revolution the revolutionary government to reward cuba. People are encouraged to come out as they were when pope francis was here. We feel the difference. You see the difference in the lack of propaganda posters here. It is all very real. Lets get perspective from someone who covered this for a long time on different levels. Jim acosta and also ed is on the rainy streets of old havana. It is a beautiful moment to witness history, always when it is a supposed step this the right direction. But these guys have cuban roots and it makes it more significant. You are on the streets all alone. Not just your popularity but something else. Set the mood for us. Were not that alone, chris. Moments ago, the president ial motorcade came by here. You see this family right up here that we have been talking to them throughout the day. They let us on the roof a while ago and we were told by security agents to get off the roof and come down here. A short while ago, the president s motorcade drove by 20 feet here and got a close up glimpse of what exactly cubans live like, what they have to deal with and this is the these are the a lot of people love to come and see the old architecture of the city. This is the reality. Many people who live in staggering, depressing conditions. The president seen up close on this motorcade. All of these people here, small group, not many people standing on the streets. Incredibly excited as the motorcade came by. The gentleman that you just saw told me it was emotional to see and experience what that scene was like. Obviously the limo is something that many people have been waiting to see. These people cheering loudly as the president ial motorcade came by. The moment didnt last long but you know for these people it is a moment they will remember for quite sometime. Now the president ial motorcade and the first family beginning the tour of old havana. An incredible moment to see this motorcade making its way down this famous boulevard here in havana. As you know too well from your reporting an Family Experience this was a moment that was never supposed to happen. So much a part of the formation of the revolution was framing the United States as a great oppressor. No president has been here since the revolution started and heres president obama now. No question it is history. The question is what does it mean . Lets bring in jim acosta. Waiting on president obama. He addressed the Embassy Staff is moving to the next location. Not the best weather for it but to go over that. Its more of what it symbolizes than reality. What are we expecting . We know president obama and first family are in the palace and armed with umbrellas as they take in old havana. This is to show the first family traveling in cuba and to say to the rest of the United States its okay to come. Part of that is because the white house is bringing with them ceos from places like marriott, starwood hotels. They signed a big deal here. They want to make it irreversible for the next president. When the next president comes in they have all of these big corporations invested here and they cant put the toothpaste back in the tube essentially. Citric i can. They dont own the ground or building. They own the Management Rights and the money will go to the government. Thats the big x factor, right. Does it get to the people on the streets who need so much . Live pictures. This is the walk about. As jim acosta was pointing out, this is symbolic and showing presence. All day long we saw people wearing obama pins. These streets arent that full and that is relevant, as well. I think its raining on his parade a little bit arriving in cuba. You are going to see cubans embracing i think the president over the coming days, everybody we have talked to since we have been on the ground in cuba is positive about the trip. They are happy to see president obama here. They see him as a different kind of president. Not the imperialist United States that they have been told to hate all of these years. Pretty soon here, chris, the president will go to the cathedral in havana and tip his hat to pope francis who helped negotiate the opening of relations. People forget the Deputy National security adviser was traveling in secret to the vatican, to canada to broker this thing. Thats how i sensitive it is. Interesting detail on that. As we look at a live picture in shah ha vanna cuba. This is history. This is an absolute. No u. S. President has been on cuban soil since the revolution began. That period has ended. What you were talking about, jim acosta, ben rhodes, the president s adviser trying to make this happen with the vatican. Who was he meeting with on the cuban side, raul castros son who runs the equivalent of the cia here and has theories of how bad the United States government is. It is part of the tension working here. One of the facts here as well. The vatican played a role. Hand delivered letters to the pontiff. And it gave cover to both gentlemen and opportunity to both gentlemen. The question is what was in those letters. That we dont know. I think what the white house looked for when they were dealing with pope francis was political cover. It is easy to push through a new policy on the American People when you have the goost Good Housekeeping seefl approval. Pope francis was talking about Climate Change and immigration and he feels strongly about the United States and cuba getting over this disagreement they have had the last 50 years and start a new chapter. Will it be easy, no. Will it happen overnight, definitely not. But to see the president of the United States and first lady and the daughters, malia and sasha under a statue of jose, walking the streets, it is unbelievable. I never thought i would see this day happen. I certainly didnt think it would happen so quickly. This is happening so quickly, i think it is understandable why my twitter is blowing up. No real assurance of change of regime of oppression. Heres as well. Those silenced many examples as we saw with dissidents today, protesters today arrested right before the president arrived. This is the first step. What are we going to see . A meeting. The heads of state meet, big baseball game, the rolling stones. All of these are cultural impacts. Well see what is to come. You are looking at history and seeing the president s daughters there. What a day for them. The first lady and the man himself, president obama going through the old plaza here. Live pictures from havana, cuba. The first steps toward a historic journey. Traveling with the president all the time, it is rare when you see the whole family traveling together on an official trip. This shows how important this is inside of the obama family, inside of the obama can you imagine the president and first lady and daughters sitting around the dinner table saying where are we going next . They are here for two nights. Thats longer than the stays in asia or europe. Thats how excited the family is about coming to cuba. Those words apply to president obamas interest in his legacy. He said he didnt want the last year to be a nonevent. He took it in his hands. Executive orders are doing this, not legislation. Thats an unknown in terms of history of relations with cuba and the United States. A quick break. When we come back, it may be raining but this is hopefully a ray of sunshine metaphorically for the people of cuba. We will take you through why in a moment. Jack be nimble, jack be quick, jack knocked over a candlestick onto the shag carpeting. And his pants ignited into flames, causing him to stop, drop and roll. Luckily jack recently had geico help him with renters insurance. Because all his belongings went up in flames. Jack got full replacement and now has new pants he ordered from banana republic. Visit geico. Com and see how affordable renters insurance can be. Youre an at t Small Business expert . Sure am. 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Hes in cuba right now with the first family. This is an historic visit. Our bill weir traveled to cuba. Spent 15 days shooting what is a beautiful debut of the wonder list. Watch. Looks like boutique you may see in soho or melrose district of los angeles. And then right across the street, people are raising chickens on their balcony. Hows life in havana these days . Really hard. Its hard. Some people think change in the future. You dont think so . I hope so. Maybe for business but for the people, i dont know. New ideas. We need that. Maybe in a few years. Really . Yeah. I came here expecting to find that sentiment everywhere, but to my surprise so many seemed proud of the cuban system. Bill weir is with me now. Tell me more about that. Heres a joke someone told me. You know what the three greatest successes of the revolution are . What . Science, arts and sports and you know what the three greatest failures are, breakfast, lunch and dinner. Telling a joke like that may have got me locked up a generation ago but it speaks of a dichotomy of people who have nothing by our standards. They are rich by a lot of standards of latin american. You are guaranteed shelter as a cuban citizen. Peoples houses are falling down and so dangerous. There are 140,000 people waiting to get in to shelters. They are building shelters instead of fixing the houses where people are living in. People are surviving day by day. We know the president landed with a lot of big name ceos, air bnb ceo coming in here. Are they excited about the money coming in. The big american businesses or wary of it. More wary of it because when you think some people say they will go the way of china. Like a oneparty capitalism. But they dont have a billion people to work in factoriefacto. A lot of them dont want to be bartenders or hotel maids. Even if marriott got the green light today or mcdonalds, the cuban government will demand 51 ownership in that business. Try to convince shareholders that is a good bet. Where they cant keep the water on. The change is going to happen. Probably take longer than we are used to. When you think of a place opening up, boom, it will turn in to south beach. Not south beach yet. It will be years in the making as they try to figure out a balance between capitalism and communism. Little tease for tonight. Biggest surprise tonight . Just the condition of the place. The warmth of the people. So much love for their cold war enemy, which ends today. Vc day, victory in cuba. March 20th, 2016. What a day. Bill weir, thank you so much. All of you will not want to miss the wonder list. Tonight 10 00 p. M. Eastern here on cnn. But first, if you are a Business Traveller headed to denver, you are in for a treat if you are a beer lover. The denver microbrew tour is a way to drink like locals when you are off the clock. Im the tour guide and thats the best way to experience the city and obviously with a beer in hand. 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Anywhere else, splat. Only verizon is the 1 network for consistently fast speeds. And now if you by a Samsung Galaxy s7 edge you get one free. We are watching an extraordinary journey. There you see the president and the first family touring old havana. Moments ago, despite the rain, out there speaking with his daughters about what is quite a moment in history. There you see him inside of the ka thee daal of havana with cardinal ortega. They are looking at something u. S. President has not looked at in 88 years. Looks like a portrait of president lincoln right there. Tomorrow the president is set to meet with cubas president raul castro who will be the first u. S. Sitting president to do that, to be on the cuban soil in 88 years. Much more from havana in just a moment. Now back to politics at home. This political season has been rough and tumble to say the least. You can relive another Brutal Campaign tonight here on cnn, bush versus dukakis. It is a brand new episode of race for the white house. Heres a look. First question comes in governor, if Kitty Dukakis were raped and murdered, would you favor an irrevocable Death Penalty. So easy for caucus to react with genuine emotion, anger and right, indignation. That somebody would murder his wife. I know what its like. That is where the answer had to go. I dont, bernard. I would oppose the Death Penalty during all of my life. I dont see any evidence that it is a deterrent. I think there are better effective ways to deal with crime. We have done so in my own state. And i thought, dead. Lets talk more about it. President ial historian is with me. That is a moment, again, a moment that contained a president ial campaign, part of what did that for dukakis. You say it is about looking and appearing president ial. What was his other key mistake if. When he rode around in a tank. The thing is what i didnt know is that some young staffers in the campaign, the Dukakis Campaign said dont this. You are not going to look good. One of the tanks, saw the helmet, put the helmet on and realized i look awful in this helmet because i have an awful nose. Governor dukakis will look just as bad. Theres the shot no one can forget. Lets contrast then and now. That was a Brutal Campaign. Now is a Brutal Campaign. Race came in to play then. Race is coming in to play now. Whats changed . Well, let me say some of it is the same. The architect of bushs campaign is someone named lee atwater who understood that politics is theater and willing to play to the worst elements of the electorate, including on race. Some of the origins of what we are seeing today can be found in the 88 campaign. But the filters are gone. With twitter and online, and little editorial control, the kind of stuff we saw in 1988 can be done without any kind of control. The famous Willie Thornton ad. Roll some of that. Bush won in all of this using racial fear to win the race and doing it successfully. Bush was a very good president but this was an ugly campaign. The will horton ad was to play on peoples fears and a rumor that dukakis had treatment for depression an reagan commented. On his mental stability. He said, i dont like to attack invalid lids. It was dirty side to the campaign and it played on our worst some of the worst feelings of this country. As i said, the question has always been what did he know about the campaign that was done in his behalf. When you look at the moment in the campaign where dan rather has an interview with george bush. There is some sort of whether it is a misunderstanding or what about what he is going in to the interview to talk about. He unleashes on rather. Part of it is bush always felt he wasnt a great president ial candidate. He wasnt treated well. They had discussed the wimp factor in talking about him. He was not a tough, ronald reagan. He was ready to go after rather, the press and to demonstrators, with his no new taxes pledge, he could be as resolute as the person he was working for. The ca