American Held By Cuba Released, U.S. And Cuba To Begin Talks On Normalizing Relations

An American freed from captivity, and potentially huge changes in America's diplomatic and trade relationship with Cuba.

Diana Nyad

This morning it was announced that Alan Gross, an American who has been held in a Cuban prison for the past several years on charges that the was spying for the United States, has been released as part of a deal that apparently includes the release of three Cubans held by the United States. More important that the prisoner swap, which is something that has happened before, is the announcement that the United States and Cuba are set to begin talks about normalizing a relationship that has been largely frozen since President John F. Kennedy broke diplomatic relations with the Castro regime in January 1961:

 WASHINGTON — The United States will open talks with Cuba aimed at restoring full diplomatic relations and opening an embassy in Havana for the first time in more than a half century after the release of an American contractor held in prison for five years, American officials said Wednesday.

President Obama plans to make a televised statement from the White House at noon about the breakthrough, which opens the door to a major international initiative that could help shape his legacy heading into his final two years in office.

Mr. Gross, who has been serving a 15-year sentence in a Cuban prison for trying to bring Internet services to Cuba, was released and put on an American government airplane bound for the United States, officials said. His captivity has been a longstanding obstacle to Mr. Obama’s desire to transform relations with the island nation.

“Today marks the beginning of a major new chapter in U.S.-Cuban relations,” said Julia Sweig, director of Latin American studies at the Council on Foreign Relations. “Finally we have an American president willing to do the right thing for the national interest, for American standing in Latin America, and for the Cuban people.”

Mr. Obama has long said American policy toward Cuba has failed to achieve the ends it was intended to achieve and over the years he has made modest changes to restrictions on travel and contact. But it has frustrated him that he has not been able to make more significant changes until now.

News agencies reported that President Raúl Castro of Cuba also would speak at noon about relations with the United States.

As part of the larger agreement, the United States is releasing three Cuban spies first arrested in Miami in 2001. American officials denied that they were being traded for Mr. Gross and said they were instead being swapped for another person imprisoned in Cuba who is believed to have worked for United States intelligence agencies.

“Not swapped for Alan Gross,” said one official.

Mr. Gross’s sister, Bonnie Rubinstein, was “beyond ecstatic” at the news of his release, according to her husband, Harold. “We are extremely grateful that he’s on his way home,” Mr. Rubinstein said by telephone from Dallas. “It’s been a long ordeal.”

American officials made no immediate comment on how the release was obtained. In the past, government officials, including Secretary of State John Kerry, have publicly ruled out a prisoner swap for three Cuban spies convicted of federal crimes in Miami in 2001.

But Mr. Gross’s health has been failing. He has reportedly lost more than 100 pounds in prison and is losing vision in his right eye. He went on a nine-day hunger strike in April. After turning 65 in May, he told relatives that he might try to kill himself if not released soon.

Mr. Gross was in Cuba to deliver satellite telephone equipment that was capable of cloaking connections to the Internet when he was arrested in 2009. The Cuban authorities, who tightly control access to the Internet in their country, initially said he was a spy, and a court there convicted him of bringing in the devices without a permit as part of a subversive plot to “destroy the revolution.”

Mr. Gross’s case drew increasing attention as his health deteriorated. He grew despondent and talked of suicide, and his wife, Judy Gross, and other supporters made urgent pleas for his release, but off-and-on diplomatic talks seemed to go nowhere.

Cuba has often raised the case of three of its spies serving federal prison time in Florida, saying they had been prosecuted unjustly and urging that they be released on humanitarian grounds. State Department officials insisted that the cases were not comparable and that Mr. Gross was not an intelligence agent.

Mr. Gross worked for Development Alternatives, of Bethesda, Md., and had traveled to more than 50 countries as an international development worker. The company had a $6 million contract with the United States Agency for International Development to distribute equipment that could get around Cuba’s Internet blockade, and Mr. Gross had made four previous trips to Cuba in 2009.

More from The Washington Post:

Cuba has freed American contractor Alan Gross after five years in custody as part of a prisoner swap that could herald sweeping changes in U.S. policies toward the island after decades of sanctions, a senior Obama administration official and news reports said.

As part the rapprochement, U.S. and Cuba will start talks to normalize diplomatic relations, which could include opening an American embassy in Havana in the coming months, the Associated Press reports, citing U.S. officials.

President Obama was expected to make a statement on Cuba at noon. At the same time, Cuban President Raul Castro was scheduled to address his nation about relations with the United States, Cuban state television reported.

Any moves to close the rifts would mark a significant moment in Western Hemisphere politics.

The United State has maintain various sanctions against Cuba for more than five decades as one of the most enduring holdovers from Cold War-era standoffs. The two countries do not have full diplomatic relations, but allow interest sections to handle outreach.


The president has taken some steps to ease U.S. restrictions after Raul Castro took over as president in 2010, including lifting travel and financial blocks on Americans with family in Cuba. Obama, however, has so far gave no indiction of plans to fully drop the embargo.

We’ll get more details about what we are likely to see going forward when the President speaks later today, obviously, but it’s worth noting that the President’s ability to unilaterally negotiate with the Castro regime is significantly by a number of circumstances. One big factor, as always, is the issue of the Cuban-American community in Florida and how they are likely to react to any deals between Washington and Havana. In the past, it has often been said that the Cuban exile community would not accept anything approaching normalization of relations with Cuba while the Castro brothers were alive and in power, and not unless the question of the status of the property that many of them left behind when they left Cuba in the wake of the revolution some 50-plus years ago was resolved to their satisfaction. To some extent, the political power of that segment of the Cuban-American community has deteriorated as they have aged, and polling has indicated that their descendants, who were largely born here in the United States, do not share the strong feelings that many of their elders do. Additionally, the Cuban-American community does not carry the same political weight in Florida that it has in the past thanks largely to migration to the Sunshine State from other parts of the country. Therefore, the political risks of discussing a more open relationship with Cuba are arguably far less than they used to be.

Notwithstanding the changed political situation, though, President Obama’s hands are still somewhat tied by the fact that many parts of the embargo against Cuba are codified into law, principally as part of the Helms-Burton Act of 1996, which placed most of what President Kennedy had originally signed as an Executive Order into the United States code. What this means, of course, is that full normalization of relations between the U.S. and Cuba will require the consent of Congress at some point. On that point, it is worth noting that the politics of this issue are not quite as divided as you might think. There are Democrats such as New Jersey Senator Bob Menendez who are at the very least reacting cautiously to this morning’s news while other Democrats are being more positive. On the Republican side, there are Republicans such as Florida Senator Marco Rubio who have been highly critical of moves to normalize relations with Cuba while the Castro family is still in power, and other Republicans like Arizona Senator Jeff Flake who have been more open to the idea in their public statements. Indeed, Flake is one of the American politicians on the plane with Gross this morning as he returns, along with Vermont Senator Patrick Leahy. What this suggests, obviously, is that the fact that the GOP is taking over Congress does not necessarily mean that it will be impossible to get Congress to act on this issue. In addition to the explicit bars to action in Hels-Burton,, there are some areas that will require Cuba to meet certain conditions, including free elections, legalization of trade unions, and other steps, before other actions can be taken to normalize relations. This, of course, is one of the many reasons that talks between the two nations will be complicated, and that full normalization may take some time. In the interim, though, there are some things that the President will be able to do without Congressional approval. This includes removing Cuba from the list of state supporters of terrorism and the lifting of at least some travel and trade restrictions that are likely to make travel to, and trade with, the island nation, far easier than it has been at any point in the past 53 years. If nothing else, that will be a significant step forward in a relationship that has been moribund since the darkest days of the Cold War.


FILED UNDER: Congress, Latin America, Terrorism, US Politics, , , , , , , , , , , , , , , , , , , , , , ,
Doug Mataconis
About Doug Mataconis
Doug Mataconis held a B.A. in Political Science from Rutgers University and J.D. from George Mason University School of Law. He joined the staff of OTB in May 2010 and contributed a staggering 16,483 posts before his retirement in January 2020. He passed far too young in July 2021.


  1. C. Clavin says:

    And one of the most productive and successful Presidencies continues apace.

  2. humanoid.panda says:

    Who you reckon is going to be the first to scream Obama is a Communist/pussy/appeaser over this?

  3. Ron Beasley says:

    It’s about time. Our Cuba policy has been absurd for decades. F##k Rubio!

  4. Modulo Myself says:


    I’m looking forward to the mid-sentence shift from praising rectal hydration to denouncing Castro’s prisons.

  5. OzarkHillbilly says:

    there are some areas that will require Cuba to meet certain conditions, including free elections, legalization of trade unions, and other steps, before other actions can be taken to normalize relations.

    Right. Sure. Because Republicans are so pro-union. Especially for public employees. And free elections are so important to them. That’s why they want voter ID. Especially for poor blacks and Hispanics. Right.

  6. Modulo Myself says:


    Well, Castro only faced a CIA-sponsored invasion once. And there were only probably 1,000 or so plots against his life. Your average Republican has to deal with Obamacare, illegal immigrants, gay weddings, taxes, and a falling crime rate. You have to keep it in perspective. Castro: paranoid dictator who replaced the lovely Batista and had no reason to distrust the enormous country 90 miles away. White Republican: righteous pilgrim beset by big-government Nazis.

  7. Neil Hudelson says:

    This is ridiculous. Sure, our tactics have achieve none of our goals for the past half century, but that doesn’t mean we wouldn’t see results during the next half century!

  8. stonetools says:

    This is big. Maybe the biggest FP advance in the last 20 years. Talk about Presidential legacy! Obama is building a great one.

  9. stonetools says:


  10. SC_Birdflyte says:

    I’m not sure of the exact date, but I believe that the embargo was imposed at the end of the Eisenhower administration, not under JFK. Regardless, it’s a policy that no longer has any rationale – if it ever did.

  11. C. Clavin says:

    Apparently Pope Frank was instrumental in getting this going.
    I’m really liking that guy.

    I think it’s time for Doug to write another post about how the last two years of the Obama Presidency are going to be uneventful.

    Man…this guy is getting shit done.

  12. JKB says:


    The Cuban Assets Control Regulations, 31 CFR Part 515 (the “Regulations”), were issued by the U.S. Government on July 8, 1963, under the Trading With the Enemy Act in response to certain hostile actions by the Cuban Government.

    I’m fairly certain that Kennedy had a few more months in office when those regulations were issued. And Eisenhower was long out of office.

  13. gVOR08 says:

    @C. Clavin: I’m also liking how the ominous Vatican review of US nuns turned out under Francis.

  14. michael reynolds says:

    Good for Mr. Obama and Mr. Kerry. Well done.

  15. Tyrell says:

    I have been in favor of some improvements in our relations with Cuba. I think that we should seek agreements that allow the internet, investors, businesses, organizations, and churches to freely operate in Cuba. US sports organizations would get involved with someday a MLB team there. The other major league sports could do well there, including NBA, NFL, NHL, NASCAR, and WWE. People would like to see Cuba once again become a vacation place for Americans. Cuba has a lot to gain from this. That is why the government must insist on human rights, basic freedoms, and fair treatment of their people.
    Experts have believed that Raul Castro and the Cuban leadership team have been ready for some time to change to a free market society that gives opportunity to all.

  16. michael reynolds says:

    Now begins the commentary pause until our right-wing friends are told what to think by Rush Limbaugh and Roger Ailes.

    It’s complicated because Sen. Jeff Flake is giving Mr. Obama some diplomatic cover.

  17. MikeSJ says:

    I have never understood why Cuba is seen as some special fount of evil that must be kept at arms length.

    Even now with all requests that they have need to have elections and change to a free market.

    That would be nice but what about China? Last time I checked they weren’t so free over there and nobody is wigging out over it.

    Oh yeah. Our good friend Saudi Arabia. Real nice people running it last time I checked.

    This nonsense over Cuba is 30 years past it’s sell by date. This is long overdue.

  18. stonetools says:

    @C. Clavin:

    I think it’s time for Doug to write another post about how the last two years of the Obama Presidency are going to be uneventful

    One of these days Doug is going to grudgingly, obliquely, and with many qualifications, admit Obama is a good President. Watch closely for it, because it will be in a brief aside. Anything more and his Pajamas Media and friends will come down on him like a ton of bricks, and he’ll lose forever any chance at right wing pundithood. But I bet some such admission will happen.

  19. Rick DeMent says:


    Who you reckon is going to be the first to scream Obama is a Communist/pussy/appeaser over this?

    … and the winner is … Marco Rubio!!!!

  20. michael reynolds says:

    @Rick DeMent:

    He just reconfirmed what I’d intuited, to whit that he’s a pathetic little twat.

    Big question now: what will Jeb Bush have to say?

  21. Scott says:

    It seems to me our embargo has kept the Castro brothers in power far longer than if we had diplomatic relations all along just like with other authoritarian regimes. If we opened up earlier American money would have corrupted Cuba into the modern age.

  22. Scott says:

    @Scott: And Ted Cruz and Marco Rubio (or families) may never have left Cuba to annoy us.

  23. C. Clavin says:

    @Rick DeMent:
    Just to be clear…Rubio and Menendez, et al are arguing for keeping a policy that has been an abject failure for more than 50 years. I mean….there isn’t even a question about it’s efficacy. And yet…there they go again.

  24. OzarkHillbilly says:

    @Modulo Myself: You are right of course, the tyranny of public teachers unions must be destroyed and the Republicans are just the ones to do it.

  25. OzarkHillbilly says:

    @Scott: I knew I hated Castro for a reason!

  26. C. Clavin says:


    I remember about a year ago sitting at a dinner where the featured speaker was a senior US diplomat involved in Iran policy. In response to skeptical questions about the Obama administration’s approach to Iran, he laid out the case that economic sanctions could work. The Iran measures, he said, were textbook examples of effective sanctioning — they were broadly multilateral in terms of who was imposing them, they were targeted at things the regime especially cared about, and they were limited in their aspirations.
    “So what about Cuba?” I asked.
    It was a bit of a jerk question. The diplomat in question simply wasn’t in a position to admit the obvious corollary. But the Cuba embargo is wholly unilateral, meaning no other country joins us in imposing it. It’s also completely untargeted, hitting essentially all sectors of the Cuban economy. And most of all, it’s utopian in its goals targeted not at specific aspects of Cuban policy but at the very existence of the Cuban regime.
    In essence, America’s Cuba policy is a textbook case of an embargo that makes both the United States and the target country somewhat poorer without any realistic hope of accomplishing its goals.

  27. anjin-san says:

    Welcome news, and long overdue. It’s remarkable that our failed policy towards Cuba has hung on for half a century.

  28. Rafer Janders says:

    @Neil Hudelson:

    Sure, our tactics have achieve none of our goals for the past half century, but that doesn’t mean we wouldn’t see results during the next half century!

    Alll we needed was another 100 Friedman Units!

  29. humanoid.panda says:

    @michael reynolds: I saw on Twitter that he actually made positive noises about this. He is either totally misreading the primary electorate, or making a bet that since they will view him a RINO anyway, he can just ignore the hard right and for the 40% sane voting block.

  30. Modulo Myself says:

    The thing is–this is not a remarkable triumph for Obama. It’s huge news, in the same way that a hoarder finally getting around to throwing out ten years’ worth of newspapers and magazines is. The hoarder was keeping them just in case Daddy Reagan walked back through the door after having left for groceries a decade earlier. Now the hoarder is one step closer to being able to walk from their bedroom to the kitchen without having to be afraid of being crushed by rest of their junk. Good work!

  31. stonetools says:


    It seems to me our embargo has kept the Castro brothers in power far longer than if we had diplomatic relations all along just like with other authoritarian regimes

    The US normalized relations with Vietnam 20 years ago. Nowadays not only is Vietnam a trading partner but it’s our secret ally in southeast Asia helping to keep Chinese ambitions in check.Heck, US Navy ships docked in Vietnam last year.
    I see no reason why the same thing can’t happen with Cuba. I expect the Republicans to try to deny Obama a legislative victory, but I think full normalization in short order is inevitable.

  32. michael reynolds says:

    I actually don’t think this issue will have any significant impact. It’s like Obama’s shift on gay marriage, another case where the logic is simply unassailable. This move will lance the boil, and the issue will get no play in the primaries. Two years from now the Congress will quietly normalize US-Cuban relations, and ten years from now no one will have any idea why we had this stupid policy to begin with.

  33. stonetools says:

    @michael reynolds:

    It does like the Republicans are gearing up to oppose Obama on this, but I gotta think that sheer commonsense will prevail, hopeless optimist that I am.
    I think that even the Cuban community will support this. Much of the first generation will oppose this move (“Give us back our sugar plantations and factories!)” but I bet the second and third generation will be overwhelmingly in favor.

  34. stonetools says:

    Obama, BTW, seems to be continuing with his new approach of “I no longer give a flying f@#k about compromising with the Republicans, I’m just going to do what’s right and let the chips fall where they may.” I’m loving it.

  35. humanoid.panda says:

    @michael reynolds: Maybe, but I think that you are underestimating the extent to which this issue triggers all sorts of Republican buttons (Obama! Executive Action! Communism!). Also, by 2012, no one in the GOP besides Santorum wanted to talk about gay marriage, while we’ve already seen one presidential hopeful (Rubio) and one major neoconservative voice (Graham) come out guns blazing against the normalization.

  36. C. Clavin says:

    Can’t wait to buy some legal cuban cigars…maybe blow some smoke in the face of Republican friends.

  37. michael reynolds says:

    No one gives a damn outside a few octogenarians in Miami. The Cuban community is trending pro-normalization at a rapid clip. And Republicans don’t need an excuse to hate Obama.

    Also, bear in mind there’s more than one ethnic group with a dog in this fight. Jews vote too.

  38. C. Clavin says:

    They are out there guns mouths-a-blazing…but in typical Republican fashion they have nothing to offer. Like Immigration and Health Care, with the Embargo all they have to offer is clinging onto a broken system.
    Offer up some alternatives…options. Obama has never closed the door on any opportunity for that. Republicans are simply unable to walk through the door.

  39. JR says:

    @michael reynolds: This. Hell, Obama won the young Cuban vote in 2012. The only people who really care about this are Cubans who felt that JFK abandoned them during the Bay of Pigs. So they are either 6 feet under or on their way out.

  40. Guarneri says:

    @C. Clavin:

    It’s hard to argue with that. What with both chambers now under. Republican control, and the house with more seats than I can remember.

    You’re doing a heckuva job, Bammy.

  41. Will says:

    @C. Clavin:

    You expect us to believe you actually have friends and that some of them are Republican?