(bell dinging) (lively music) (news announcer) The U.S. threw up a steel fence, prepared to stop any vessel carrying materials at war.

(President Kennedy) Shall be the policy of this nation... a strict quarantine on all offensive military equipment.

(Cray) The U.S. embargo against Cuba is one of the longest cases of economic sanctions.

Recent openings and closings have left Cubans in a world full of uncertainty.

♪ In Havana, a soccer league lifts up Cuba from the inside.

And an independent fashion brand solves their way to a pop-up shop in Brooklyn, New York.

(President Obama) I have come here to extend the hand of friendship to the Cuban people.

(woman) What is the Cuban dream?

I know what it is for me.

But what is it for you?

♪ (indistinct conversation) (soft upbeat music) (Carlos) My grandfather in here.

♪ You know, the original document states that the embargo is in place in order to wreak havoc on Cuba.

The end goal of the embargo has always been regime change.

♪ There is a belief that what Cubans want, that the way we can help Cubans, is by ensuring that there is a democratic system in place.

♪ I don't think that Cubans go to sleep at night hoping for a multiparty democracy.

I think Cubans go to sleep at night hoping for a new car, hoping for a house, a different house perhaps, hoping for an annual vacation maybe outside of Cuba.

What Cuban people want is not what we think they want.

(players shouting) (players talking, shouting) (speaking Spanish) (birdsong) (upbeat music) (Cray) So here we are, Concord, Massachusetts, and I know what you're thinking, "This is a film about Cuba.

What are we doing on the Old North Bridge?"

And the thing is a revolution started right here.

(military drums pounding) (Doris) Cuba was the major foreign policy in 1960.

The Revolution had taken place.

You have a communist government 90 miles from the United States.

So suddenly, the Cold War, which is at its height then, is very close to home.

It's hard now when we talk, the words "Cuban Missile Crisis," it seems like this moment in history and it's gone and it all turned out all right.

(news announcer) Tuesday, the 2nd day of crisis.

Reaction at last from Moscow.

(Doris) So you forget this was the point when Russia and the United States were arguing about something really important, when there were missiles put in Cuba that could reach us within minutes.

(news announcer) Possessing the offensive weapons to deliver in two minutes thermonuclear destruction.

(Doris) I was in that generation in the '50s when, you know, we would practice, "Where would you go if 30 minutes from then the nuclear bomb is going to hit New York and it might hit us?"

(video announcer) Duck and cover underneath the table or desk.

We make fun of the fact that we would go under our desks in school.

-You cover.

-But there was a real sense among a generation that the whole world could end.

That's the famous 13 days, of course, that Robert Kennedy writes about, but during that time there was deliberation, there were feelings about, "What can we do where and what are our options?"

And he decides upon the embargo rather than the bombing or rather than attempting some other invasion.

(dramatic music) (President Kennedy) All ships of any kind bound for Cuba, from whatever nation or port, be turned back.

(Doris) My husband Richard Goodwin was very instrumental in Cuban-American relations in working with JFK.

So at 29 years old, he is on the plane with JFK throughout the entire presidential campaign.

JFK had to give a speech about Cuba with all the Latin American representatives, and Che Guevara was there.

He saw that my husband was younger and perhaps more open than many of the other delegates.

Okay, Cray.

Now I have to show you the cigar box.

So that night, he sent a box of Cuban cigars to my husband's hotel room with a Spanish note in it saying: "Since I cannot speak to an enemy, I extend my hand with these cigars."

(Cray) This was a memo that... (Doris) It came with a full box of cigars obviously.

-Right.

-That's when he brought them back and gave them to Kennedy and sadly Kennedy took so many of them away.

(somber music) ♪ (Carlos) Perhaps there was an image here that Cuba was made up of 11 million people dressed in olive green.

(news announcer) Castro has put every able-bodied man through military training.

Yes, in the Cold War there was a very clear distinction of who is a national security threat and who is not.

In 1962 was the Cuban Missile Crisis.

Today, I have a hard time believing that Cuba is a national security threat.

Everything in Cuba in recent years, all that extraterritoriality will one day backfire on us.

So we are punishing European companies, Canadian companies, Latin American companies if they do business with Cuba.

And Cuba at the same time, without President Obama, started their own process of allowing private businesses.

(lively music) ♪ (knocking) -Hi, Cray!

-Oh, hey, Bernadette!

-Welcome!

It's great to see you!

-So good to see you!

-Excited to talk Cuba?

-Yeah!

(Bernadette) So when you're thinking about ways to make a breakthrough when there are such stark differences between the governments, right?

The U.S. government, the Cuban government.

The Cuban people and the American people, you don't really know what to make of each other.

We have lots of Cuban Americans here, but this is new for everybody.

And how do you break through?

It's certainly not by talking about you turn transactions and bypassing, you know, banks, and how do you get credit flowing?

Like that's interesting, but it's not really fun.

It doesn't really grab your attention.

(President Obama) So nice to see you.

There is this comedian in Cuba named Pánfilo who everybody knows, and he's amazing and he's funny and he embodies everything that is great about the Cuban spirit.

Ben Rhodes was very supportive, Terry Szuplat, who was the speechwriter at the White House at the time.

(Ben) People watch the news, but people also like to watch comedy shows.

People also like to be entertained in different ways.

And the fact is part of diplomacy, part of public diplomacy in this day and age is trying to meet people where they are, and where they are is watching Pánfilo.

And sure enough, sitting at the Resolute desk, President Obama and the Oval Office of the White House had this phone conversation with Pánfilo.

(President Obama) This is President Obama.

(Bernadette) And then when we went down to Havana, we had Pánfilo's crew come and they built an exact replica of the set.

And President Obama rolled in and we had huge cue cards for him.

(President Obama) Mucho gusto!

He likes to think he speaks really good Spanish.

I think he speaks okay Spanish and so we had these cue cards with all of the accent marks and, "Here's what you need to say."

Hello.

(Ben) We wanted to find other ways to reach Cubans.

We had heard from our embassy that this was the program that reached the most Cubans, that Cubans really appreciated Pánfilo.

So we reached out to him, I think he was surprised at first.

"The President of the United States would want to do something like that?"

(men) ♪ Obama, Obama ♪ ♪ It's good that you're visiting Havana!

♪ (Ben) Cuba is only 90 miles away from Florida, but we've been separated by this vast gulf of the Cold War, by an embargo... (President Obama) That's a beautiful song!

Thank you so much!

(Ben) ...by these adversarial policies.

For all the history that has divided us, there's a culture that has fundamentally brought us closer together.

And frankly, for all the tension in our relationship, the fact that we could laugh together I think sends an important message that we're really not all that different.

(President Obama) Okay.

Thank you very much!

(clapping) Good seeing you guys!

Take care.

(mellow music) ♪ ♪ ♪ (waves crashing) (soft music) (Bernadette) It was my job to oversee, on behalf of the Obama White House, how we would do that public rollout.

How would we announce this to the world?

How would we explain to the average American why this mattered?

In the end, you have to be able to say, "This is why we believe these decisions we made were the right ones for the United States and the Cuban people."

Compromise is an essential part of any negotiation.

You know, it's often been said you don't sit down and make peace with your friends, you do this with your adversaries.

(indistinct conversation) Surprisingly, we argued a lot about the event that we did with entrepreneurs.

With the Cubans, it was a point of a lot of contention because they wanted to favor state-owned enterprises.

We want to focus on cuentapropistas, all of these people doing dynamic great things, Clandestina, the people who own the paladares, the people who are doing Airbnb.

(Idania) Entrepreneurship in Cuba is the future, because it's one of the most important ways that we can use to evolve our economy and our society.

And we argued for days and weeks and months over that.

In the end, we compromised and the Cubans said we must have representatives of both cooperatives and state-owned enterprises in the room if you want to have any entrepreneurs and cuentapropistas.

(President Obama) Here today to talk about the challenges you face as entrepreneurs in Cuba.

(Bernadette) And I thought, "This is a failure on my part."

I was not able to negotiate this, so it's all about entrepreneurs and I didn't achieve what I set out to do.

And in the end I was wrong.

This is the first time any Cuban government official or state-owned enterprise leader has been forced to sit in a room with an entrepreneur and listen to them and they had to do it while these people stood up and interacted with Barack Obama, the president of the United States of America.

(President Obama) I need some information on where I can buy a couple of t-shirts.

So... Did you bring some samples?

I'm not going to take yours.

They, uh--but no, no, no.

But we'll see if we can get a couple, I think Malia and Sasha might want a couple, and I still have some pesos to spend before I leave.

(quiet laughter) For Cubans who live in Cuba, they would say that those were the best two years that they've lived in a long time.

U.S. companies were going down, there was friendships taking place, people were beginning to think about opening up new businesses.

People who had their own private taxi, now they're just not making ends meet.

(somber music) ♪ All those visitors from the U.S. who came are no longer coming.

♪ President Obama chose the right timing because the Cubans were also going in that direction, the Cubans were also opening up, allowing international travel, artists to sell their wares, their paintings or sculptures.

So we came in at exactly the right time.

Now interestingly, we have pulled back and Cuba has kept going.

♪ There is a very large Cuban constituency in the U.S., Cuban American, and it is a domestic issue.

It's a domestic political issue.

President Trump has already been convinced by his people that if he wants to win Florida the hardline approach was better.

That may not be what he wants to do from a foreign policy standpoint.

During his campaign, he said the embargo has been around for over 50 years.

It's time.

♪ So we're talking here not about foreign policy.

We're talking about domestic policy.

From a foreign policy point of view, every country in the hemisphere is against the embargo.

(crowd chanting) USA!

USA!

USA!

(President Trump) We will enforce the ban on tourism.

We will enforce the embargo.

(clapping) (Carlos) My father, he was in his 40s.

He was an up-and-coming entrepreneur and he lost everything.

It's very easy, when you inherit talking points, how to feel about Cuba, what to say about Cuba, but there comes a point where you realize you need to think for yourself.

(Cray) Yeah.

(Doris) I still don't see what benefit that America has gotten from this relationship other than, you know, the understandable feelings of people who were hurt by it and who still feel very strongly that they were not just an enemy abstractly on the other side of the world, they're right there and our families were hurt by it.

And maybe at some point as time goes even further on and people are not feeling the visceral sense of anger and betrayal that they felt.

(crowd screams) You change a policy by persuading people and by changing public sentiment, and sometimes that human sight of the countries being together, like a baseball game, can begin to change people's feelings about Cuba's not this alien place down there.

Here's these people and they're playing baseball and they love that sport as we love that sport.

Open engagement would make that even more possible.

I was so hopeful when I saw the normalization under Obama and it's obviously received a setback right now, but I have a feeling that in the future it's inevitable that these two countries are going to be able to get along better.

(soft music) ♪ (indistinct conversation) (upbeat music) (salsa music) ♪