If pressed to compile a roster of people most vehemently opposed to thawing relations between the U.S. and Cuba, at first glance, you might put near the top of the list Miami, Fla., attorney Pedro Freyre, Chair of International Practice at the law firm of Akerman LLP. A third-generation lawyer and graduate of the University of Miami School of Law, Freyre conveys a family story as fraught with Horatio Alger-like drama and pathos as any usually confined to the Silver Screen.

For years, Freyre’s father had been one of Cuba’s leading labor relations attorneys. But, following the communist revolution of 1959, he still served a client list that included several large U.S. corporations and was blackballed as a capitalist lackey. After a year of seeing his law practice dwindle to almost nothing, the Freyre family joined the mass exodus of Cubans fleeing across 90 miles of open water to start their lives anew in the U.S. It was what Pedro Freyre remembers, in sublime understatement, as “A very intense experience. … A very hard time.”

Indeed.

Freyre’s brother-in-law was killed and his older brother captured in the ill-fated Bay of Pigs invasion. Shortly thereafter, his father took part in the negotiations that resulted in the prisoners of the April 1961 invasion being freed in exchange for food and medicine.

Freyre is now Chair of International Practice at the law firm of Akerman LLP. Over the years, he has become one of the most outspoken—and surprising—advocates of dismantling the United States’ 53-year-old trade embargo on Cuba and normalizing relations between the two countries.

Global Trade: Given your background and what the socialist revolution in Cuba cost your family, what led you to the conclusions you have about liberalizing relations between the U.S and Cuba?

Freyre: It’s called growing up. It’s called evolving and understanding that the world is complicated and nuanced and accepting the fact that there aren’t binary solutions to problems—black or white, up or down. My clear sense as I’ve learned more and more about Cuba is that the future of the Cuban people is in their hands and that we need to help them do the very best they can to ensure a better future for themselves.

Q: How would you define that future?

A: First and foremost, I don’t think the political morphing has progressed to any great degree, though we are seeing little glimmers based on generational shifts. I think the older generation in Cuba—the guys who fought in the mountains against Castro—are far more set in their beliefs and their positions, far more inflexible. They have more baggage, as do the folks who settled in Miami. I think you see that in all the polls. The older folks are locked into hard-line positions on both sides of the straits, while the younger folks tend to be more pragmatic and derive their opinions from their own life experience.”

Q: You’ve drawn a parallel between the economic development of Vietnam and the potential economic development of Cuba. Would you say that the generational issues you’re described also happened in Vietnam?

A: The proof is really in the pudding. What strikes me is that, speaking of the United States and Vietnam, you have two countries that were at war. We lost 56,000 people there; it was traumatic for the U.S. and Vietnam, and yet within a relatively short period of time, the leaders of Vietnam came to understand that it was in their own best interest to mend fences with the U.S. The U.S. understood the same thing and fences were indeed mended. That doesn’t mean that Vietnam has become Switzerland, but it’s embarked on a course that has afforded more prosperity to its people. Vietnam is evolving.

Q: What opportunities exist for American firms that might be interested in doing business in Cuba once trade relations are fully normalized?

A: I think the immediate opportunities involve agricultural products, pharmaceuticals; on a smaller scale, construction materials and equipment, agricultural and food-processing equipment, and pollution-control equipment. The challenge is to reestablish Cuba’s private sector and help reposition the country as a regional supply center for goods and services, in the health or agriculture industry, for example.

Q: Do you think that a free-trade agreement between the U.S. and Cuba might come about in the future?

A: That’s still a long, long way off. Free-trade agreements are for countries that are friendly partners. The U.S. and Cuba are just now sitting down at the table to see how they can solve a 55-year-old conflict. That’s going to take a long while.

Q: What barriers still need to be dismantled?

A: The first barrier is one of trust. Both sides need to learn to trust each other; that’s already started. Beyond that, there are the legal barriers that the U.S. still has, including the embargo, while the Cubans have a battery of archaic laws that they need to dismantle.

Q: Are there any barriers that shouldn’t be removed?

A: All the barriers that exist should be looked at individually, so I suspect that some things might stay in place. For example, direct financing by the government [subsidies] might be an issue, but I don’t see that in the offing just yet. All in all, though, I think it just makes sense for a bulk of the barriers to be removed.

Q: What about the export of technology that could be used for military purposes?

A: That’s one that needs to be given very careful consideration and thought. It’s not a matter of not trusting; the U.S. has friends and allies and it also has countries that it has relations with that are not exactly very friendly. Cuba and the U.S. are not friendly to each other—yet. As the relationship develops, things will improve; but I don’t yet have a vision of Cuba easing into a relationship with the U.S. just now that would position the country as an ally. I don’t think we’re there yet.

Q: Other than Vietnam, do you think that there are other countries that Cuba could use as a template to develop its economy?

A: Look at all of Eastern Europe and you can see Poland and the Czech Republic both stand out. In Latin America, there are bits and pieces of other models that you can fit together. Chile, for example, has been an outstanding example of how you can take a country about the same size (population-wise) as Cuba that has become quite prosperous.

Q: What lessons are there to be learned by both sides in this equation?

A: The first lesson is pragmatism and understanding that, anyway you slice it, both the U.S. and Cuba are neighbors; there are a lot of Cubans living here and there are family bonds that cannot be broken. Understanding the historical relationship between the U.S. and Cuba is also very important. Very fundamental things like respecting one another.

Q: Other than the generational issues and barriers, are there any other hurdles that could stand in the way of normalizing relations between the two countries?

A: None economic. But I think that at the heart of the problem is politics. Both countries are behind in understanding what their people want. The explosion of joy in Cuba when this was announced was fantastic and all the polling in the U.S. shows that a majority of the American people believe that Washington needs to normalize relations. The governments need to catch up to their people.

Q: Do you think the day will come when Cuba divests itself of its communist/socialist system?

A: Who knows? People will tell you there’s no guarantee that the government will do this or that. The truth is there are no guarantees. There are no guarantees that the United States we’re living in today will be a democracy 100 years from now. But if you look at the world and study the particular relationships between the U.S. and Cuba, you have to conclude that the embargo has been an abject failure. If the purpose was regime change, as we say in law, res ipsa loquitor [the thing speaks for itself]. It didn’t work. We need to come up with a new strategy. As to where Cuba will fall in terms of its governmental model, that’s up to the Cuban people.

Q: You mentioned the enthusiasm that was shown in Cuba when it was announced that relations with the U.S. would be taking a turn for the better. Are you seeing the same sort of response on the part of U.S. companies?

A: Definitely yes. The word that my boss uses is “unprecedented.” What we’ve seen from our clients alone is remarkable and what I’ve seen on the road doing seminars on Cuba in New York and Chicago, for example, has shown me that the level of curiosity and interest is very substantial

The first moves to normalize relations between the U.S. and Cuba, concludes Freyre, “are the beginning of a bumpy process that will have steps forward and steps backward. There are people on both sides of the street that don’t want this to happen and they’re working hard to see that it doesn’t happen. It’s fragile, but it’s a fascinating and intriguing process that is in the best interests of both the United States and Cuba.”