Big Smoke Meets WhiskyFest Is Coming May 28th. Buy Tickets Now.


Memo to President Obama

Cigar Aficionado asked a leading Cuba expert to provide a road map for improving relations between the United States and its island neighbor
| By Julia Sweig | From Cuba, January/February 2009
Memo to President Obama
AP Photo/Doug Mills

Just before Barack Obama was sworn into office as the 44th president of the United States in 2009, we published our January/February issue that dedicated its pages to Cuba and U.S. relations. In one of those articles, we asked Julia Sweig, an expert on Cuban affairs, to draft an open memo to the incoming U.S. president explaining why and how the embargo should be lifted. After President Obama's landmark announcement yesterday, we thought it appropriate to revisit the piece.

In the first six months of your presidency, you should launch an initiative to put to rest the half century of mutual enmity between the United States and Cuba. Doing so represents an opportunity of both major foreign policy reward and low domestic political risk. Mr. President, a bold initiative with Cuba, early in your presidency, will restore America's credibility and demonstrate your political courage with the Cuban people, in the hemisphere and across the globe. This memo will lay out why, provide several caveats to guide your considerations, and outline a series of concrete recommendations.


The United States has maintained an economic embargo, a broad travel ban and a host of punitive diplomatic measures against Cuba for nearly 50 years. Keeping such policies on the books any longer serves no foreign policy, national security or even substantial domestic political agenda: the status quo undermines all three. I am not the first person to argue that the time has come to open a different chapter with Cuba, nor are you the first president who will read a memo arguing as much. In fact, you are the 10th president of the United States to inherit a broken and utterly small-minded policy toward Cuba. And you are the first president since Dwight D. Eisenhower to take office when Fidel Castro was not at the helm on the island.

Unlike your predecessors, you campaigned on a program of making potentially significant changes in America's approach to the island. You spoke of talking directly with Raúl Castro, even while insisting on the importance of freeing political prisoners, bringing democracy and human rights in Cuba, and conducting appropriate advance work to ensure that talks address these agenda items. You called for an end to restrictions preventing Cuban Americans from visiting and sending remittances and other humanitarian assistance to their families on the island. And you talked about promoting people-to-people ties between all Americans and Cubans. You demonstrated the political courage to embrace these measures not only among liberal audiences, but in the state of Florida, where you saw that Cuban Americans are no longer single-issue or single-party voters. You recognized that, like many other traditional GOP supporters in 2008, Cuban Americans had lost faith with the party over bread-and-butter middle-class issues, the economic and financial meltdown, the war in Iraq and, notably, over Guantánamo. And you won the state of Florida without a political debt to hard-liners in the exile community, thus freeing the United States to craft a policy toward Cuba, rather than toward South Florida.

Today's international context also distinguishes you from your predecessors with respect to Cuba policy. In their own times and for their own reasons, Presidents Nixon, Ford, Carter and Clinton each took notable steps to break with the ineffectual policies of sanctions and isolation. But their limited openings toward Cuba occurred at moments when America's credibility on the world stage and among our allies was overwhelmingly positive. The Guantánamo Bay Naval Base—under U.S. control since 1903—has long been a symbol of yanqui imperialism for Fidel's revolution and for others on the left in Latin America, but it was hardly the negative global symbol of American power gone wrong that it is today. Indeed, with America's international standing now severely diminished by the last eight years of unilateralism and arrogance, the moves you make toward rapprochement with Cuba will have resonance well beyond their impact on the Cuban people or their government.

In the Western Hemisphere, U.S. policy toward Cuba is universally derided as ineffectual and an obstacle to the emergence of a more open, pluralistic society on the island. An opening toward Cuba will be quietly encouraged and loudly applauded by major U.S. allies in the region, such as Argentina, Brazil, Canada, Chile, Colombia and Mexico,each of which possesses extensive ties to the island and is paying close attention to developments in Cuba during this 50th anniversary year of the revolution. Havana's brashly ideological allies in the region—Bolivia, Nicaragua and, notably, Venezuela—will find a big argument in their brief against the United States (i.e. Goliath's penchant for picking on David) substantially undercut. The dozen or so small island countries of the Caribbean, meanwhile, most of which vote with Venezuela and Cuba at the Organization of American States and the United Nations will have cause for reconsidering this practice.

Beyond Latin America, Fidel Castro and Che Guevara remain cult heroes for many. Despite its human rights violations, Cuba's leadership has earned grudging respect among multiple generations of intellectuals and political leaders for its social gains and for its continued defiance of Washington. In Europe in particular, U.S. sanctions have earned the ire of many for casting their punitive reach on potential business and investment with Cuba. After a five-year freeze, and under the leadership of Spain's prime minister, José Luis Zapatero, the European Union has recently lifted economic sanctions and commenced a broad ranging dialogue on civil and political as well as social and cultural rights. A fresh approach to Cuba will send a signal that the era of American hubris in foreign affairs, at least in its own neck of the woods, may well be coming to an end. A significant dimension of the collapse of America's standing globally during the Bush years was that the United States was willing to use its power willy-nilly without a healthy degree of respect for the views of others, as the Constitution commends. For more than 15 years, the U.N. General Assembly has voted nearly unanimously in support of a Cuban resolution condemning the American embargo against it. Owning up to the failures of this policy and sending a clear signal of a new approach will gain ready plaudits from our allies, whose help we will need in confronting real, rather than manufactured and domestically driven, national security challenges.

For many of the same reasons, American public opinion is ready for a change as well, and a significant one at that. Nationally, polls consistently indicate that a majority of Americans believe they should be able to travel to and trade with Cuba and that Washington and Havana should reestablish diplomatic relations. Even among your toughest audience, the Cuban-American community, a consensus is emerging that current policy has failed and that neither the Cuban nor the U.S. government has any business getting in the way of individuals' desires to help family members on the island. Cuban-Americans also favor an end to travel restrictions for all Americans, not just for themselves. Such views have only become stronger in the wake of the devastating damage wrought upon the island by hurricanes Gustav, Ike and Paloma last summer and fall. Regardless, Cuban Americans today make up only 7 percent of Florida's electorate in national elections. Even as you recognize the importance of Cuban-American family ties and perhaps, in the future, as part of a new wave of foreign investment there, they are not the only stakeholders in building a better modus vivendi with Cuba.


Before outlining the steps you can and should take to launch this initiative, I first want to caution you about two issues.

Democracy: The first is democracy. In short, do not pursue a bilateral opening with Cuba out of the belief or hope that doing so will rapidly bring liberal democracy to the island. There was little history of it before 1959—in the past 50 years, even less. In the early 1960s, the United States could have perhaps helped prevent some of the revolution's later radicalization by finding a modus vivendi with a young Fidel Castro, who was leery of Soviet power. A full-blown opening under Jimmy Carter, or even under George H. W. Bush when the Berlin Wall fell, might also have provided space for reformers within and outside government circles in Havana to make the case for greater economic and political liberalization. Indeed, had the first President Bush or even President Clinton during his first term issued executive orders to lift the trade and travel ban and restore diplomatic relations, Cuba might look quite different than it does today, perhaps with a recognizable social democratic order, a more open economy and ample state social services. By now, the United States might well have been able to count Cuba among the Latin American countries where the American commitment to democracy had played a constructive role.

At this stage, however, to think that an end to the embargo will speedily usher in an era of multiparty elections and market capitalism would be to set your administration up for failure. Cuba is today and will remain for some time a one-party state with a controlled press and significant impediments to individual freedoms. Thus, in your own mind, and publicly, it is best to frame any moves toward Cuba as matters of American national interest. At the same time, you should assert your belief that greater openness from the United States has the potential to lay the groundwork for a more open society on the island, where human rights and personal freedom can accompany Cuba's long-standing aspirations to social justice and national sovereignty. These values are shared by Cubans on the island and in the diaspora, but their implementation would still stop well short of raising the unrealistic expectation that a new U.S. approach can accelerate a full-scale democratic and pro-market transition. A historical note worth considering: when Henry Kissinger sent a few key deputies to secretly meet with Castro's envoys in 1975, he acted for geopolitical reasons first and foremost; he harbored no illusions about the domestic impact within Cuba of an opening with the United States. Nor did he demand preconditions before sending his emissaries to talk with Fidel's. Neither should you. But be assured that a less hostile policy will strengthen those within Cuba who are already making the case for greater freedoms and economic liberties at home, but who are thwarted by hard-liners whose positions are repeatedly reinforced by the reliable hostility of U.S. policies. In that sense, by simply taking steps to remove the United States as an excuse for domestic repression, and thereby helping reduce the siege mentality that has left its corrosive mark, you will contribute, over time, to change in Cuba.

Raúl Castro's First Year: The second major issue or caveat relates to what is happening in Cuba today. In the aftermath of Fidel Castro's illness (announced during the summer of 2006) and Raúl Castro's election to the Cuban presidency in early 2008, it looked to most observers that Cuban authorities would carry out a number of potentially significant, though modest and modestly paced, economic reforms aimed at increasing the personal freedoms and material conditions of Cuban citizens. The words privatization or free market are seldom used in official Cuban discourse about changes in the economy. But by decentralizing and distributing land titles and otherwise promoting more free enterprise in the agricultural sector, lifting previous caps on wages, and announcing his intention of reducing the economic involvement and size of the state bureaucracy, Raúl has clearly signaled a new era is emerging. At times, he has sounded more like Margaret Thatcher than Karl Marx, stressing the need for Cubans to improve their work ethic, efficiency and productivity. In one major speech, for example, he cautioned that "equality is not the same as egalitarianism," which itself could be "a form of exploitation of the good workers by those who are less productive and lazy," and warned Cubans not to expect the state to foot the bill indefinitely for an enormous range of goods and service. On balance, for the first half of 2008, Cuba exuded confidence internally and internationally, with a diversified trade and investment portfolio, the financial backing of Venezuela's Hugo Chávez and new investments from Brazil, China, Spain and Russia.

By the summer of 2008, as the global food and fuel crisis hit home, Raúl began to moderate his tone, warning of impending belt tightening. Echoing his brother's historic allergy to the market, he stressed the need to protect the revolution's historical social achievements and maintain its firm resistance to empire (aka the United States). Raúl was—and still is—engaged in a balancing act, moving to gradually open the economy and permit often brutally honest public debate about economic and social issues, all while retaining political control and a major role for the state as the dominant actor in national life. All of this unfolded with Fidel Castro never far from the scene. Though physically out of the picture but clearly in better health, his regularly published commentaries on domestic, economic and international subjects appeared to both help Raúl manage public expectations but also dampen the pace of some economic openings for which many Cubans were hoping.

Then, at the end of August, and again in early September, hurricanes Gustav and Ike ripped across Cuba, inflicting an estimated $5 billion to $8 billion in damage. Much of Cuba's tobacco, citrus and coffee crops have been ruined, while poultry production and fishing fleets were severely damaged. Electrical grids in entire provinces were destroyed, as were more than 500,000 homes, displacing 2 million people and leaving 1 million jobless. The disasters have also encouraged speculation that the urgency of producing food especially could actually convince the government to accelerate private agricultural modes of production and other forms of market activity, all within the framework of socialism á la Cubana. Humanitarian and reconstruction assistance has come in, from the likes of Venezuela, Russia, China, Spain, Brazil and Mexico. But with the global financial crisis adding a climate of risk and uncertainty to Raúl's tentative steps toward modest reforms, not to mention the possibility that social pressures internally and to migrate will increase, the Cuba you will likely engage will be focused on recovery and reconstruction more, at first, than on reform and renovation. As always, Cuba will be wary of the United States and unwilling to frame any movement, domestic or bilateral, as anything approaching a concession to its historic nemesis. The stability of Cuba's succession from Fidel to Raúl has been smooth and remains so, a disincentive, some would argue, for you to spend your energy on a new approach to the island. Changing policy toward Cuba is strongly in the American national interest. It is the right thing to do. And there are other excellent reasons to put your energy into a new Cuba policy, as I have outlined above. But with Cuban officials warning of severe food shortages well into early 2009, the last thing you need is the kind of instability in Cuba that could prompt a mass refugee exodus. The time to talk is now.


The remaining portions of this memo lay out what the executive branch can do to fundamentally recast American policy toward Cuba. I also note where Congress will be key. The goal of the steps outlined below is to set into motion a process that, in the short to medium term, will bring about the end of the trade and travel embargo while establishing the initial items for an agenda of bilateral talks.

Travel: In the first hundred days of your presidency, you should issue an executive order revitalizing and liberalizing the 13 existing categories of licensed "purposeful" travel, which promote contact with the Cuban people for all Americans, following the path chartered by the Clinton administration in preparation for the 1998 papal visit to Cuba. At the same time, and consistent with your campaign pledges, you should repeal all restrictions on Cuban-American family travel and remittances imposed since 2004 by the Bush administration. These two steps will not result in the complete elimination of the travel ban. Congress will need to finish that job with legislation eliminating all travel restrictions.

Trade: With your authority, you can also license the sale of goods and services that serve humanitarian purposes, especially as pertains to public health and all other materials that can assist in Cuba's recovery and reconstruction efforts in the wake of the recent hurricanes. Since the Cuban government is already the exclusive buyer of food under a 2000 law permitting such sales between our countries, legal precedent and practice exists for the government to also purchase other goods. You should allow Cuba to purchase non-agricultural goods on credit and make it easier to purchase American agricultural products using a more liberal interpretation of the statuatory credit restrictions, a move already urged by U.S. farm organizations. Congress can then eliminate the remaining anomolous credit restrictions on agricultural sales.

Talks: Much hoopla was made over the answer you gave to a campaign debate question about whether you would talk directly to the Cuban leadership. You were right on foreign policy grounds to say you would, and to later stipulate as a matter of principle that doing so in no way meant your administration would condone Cuba's often egregious human rights practices and authoritarian nature. On a number of occasions, Raúl Castro has indicated his willingness to talk on a range of issues: the precondition he has advanced is one of respect for Cuba's national sovereignty. Despite ongoing antipathy, public recriminations and a variety of American laws aimed at regime change, the United States and Cuba actually have a history of talking with each other almost continually over the last half century—whether through back channels, formal channels or third parties.

For example, after secret negotiations produced an immigration agreement in 1995 allowing 20,000 Cubans to migrate legally to the United States each year, teams from each country met twice annually until 2004 to keep the agreement on track. Likewise, to this day, the American and Cuban commanders on either side of the gate at Guantánamo meet with their counterparts each month. Both sets of talks demonstrate the capacity on both sides for pragmatism, especially when it comes to the essentials of national security. In this vein, your administration should "pursue talks on issues of mutual concern to both parties, such as migration, human smuggling, drug trafficking, public health, the future of the Guantánamo naval base and environmentally sustainable resource management, especially as Cuba, with a number of foreign oil companies, begins deep-water exploration for potentially significant oil reserves." This recommendation of direct talks is hardly controversial. It comes directly from the Council on Foreign Relations and is echoed by a host of leading lights of foreign policy from both political parties, individuals who recognize that diplomacy is not about popularity and favoritism, but an essential tool for promoting the national interest.

There is no pressing reason for you to meet directly with Raúl Castro at this time. Too much groundwork lies ahead before such a meeting would make sense from a foreign policy or domestic political perspective. Well before any such encounter, the United States and Cuba need to embark on a series of talks aimed at establishing common sense cooperation to serve both countries' national interests. If a meeting between you and Raúl Castro appears, down the road, to have potential to significantly advance American interests with respect to Cuba, you should consider participating. And there you can advance a discussion about democracy and human rights, as your counterparts in Europe and Latin America have as well. In that vein, be prepared to hear from Cuba about its own view of human rights in America, in light of Guantánamo. I can assure you that, while clearly willing, Raúl Castro exhibits no sense of urgency to meet with you and has a coterie of senior advisers and experienced negotiators upon whom he will rely instead. In the meantime, the relevant cabinet, national security and military officers in your administration will have to inoculate the individuals they task with shaping and carrying out these talks from the kinds of political pressures that have in the past undermined attempts at conducting a rational, non-ideological approach to American policy toward Cuba. In short, if you want these talks to succeed, as they have in the past under Presidents Carter and Clinton, senior officials in your administration will have to guide them, making it known they are acting at your instruction and under your scrutiny. Simply tasking the bureaucracy—long accustomed to and hampered by ineffectual and politicized thinking on Cuba—to start the talks will doom this initiative.

Unilaterally, you should follow the recommendations of terrorism experts in both parties to remove Cuba from the State Department's list of state sponsors of terrorism. The Reagan administration first put Cuba on the list because of its support for leftist rebels in El Salvador. For purely political reasons, the State Department has subsequently kept Cuba on the list, even as Libya and North Korea have been removed. Then, the substantive issues pertaining to American fugitives in Cuba or anti-Castro Cuban terrorists, such as Luis Posada Carriles, now free in the United States, can be addressed in bilateral talks involving the FBI, Justice Department and their Cuban counterparts. Likewise, be prepared for American allies and for the Cuban government to press the case for the release of the Cuban Five, the intelligence agents who in the late 1990s infiltrated South Florida exile groups, produced intelligence on pending terrorist attacks against Cuba, and who, after the Cuban government passed the information to the FBI, were promptly arrested, tried and convicted, in some cases, to multiple life sentences.

Congress: As with American public opinion generally, there is a latent bipartisan consensus in Congress to lift the embargo. Legislation to lift travel and trade sanctions passed between 2000 and 2002, but was stripped in conference when the GOP leadership worked with Cuban-American Republicans in the House and with the White House to prevent any liberalization of Cuba policy. Now, with a stronger Democratic majority in the House and Senate, and especially because of the severity of hurricane damage to Cuba, you can expect to see legislation calling for an end to restrictions on Cuban-American travel and remittances and on all American travel to Cuba. You can also anticipate bills calling for a suspension of the embargo, its complete elimination or possibly even the repeal of Helms-Burton. Indeed, leading Republicans in both chambers have already joined their Democratic colleagues in advancing a range of such initiatives. Likewise, there is bound to be legislation to significantly boost aid to promote democracy, civil society and human rights. These programs have rightly come under scrutiny for corruption and ineffectiveness in recent years. Secretary of State Hillary Clinton should work with the key appropriations and authorizations committees to cleanse from the U.S. Agency for International Development all vestiges of programs that smell of regime change. They are ineffectual, they hurt genuine reformers on the island, they provoke the Cuban government to no apparent end and they diminish the credibility of America's real bona fides on democracy, as well as those of Cuban dissidents.

Politics: In your campaign you argued that you would keep the embargo in place to use it as leverage to extract democratic reforms from the Castro government. Mr. President, don't hold your breath. When you campaigned to open up Cuban-American and people-to-people travel and said you'd pursue talks with Cuba, you made sense to all but the most passionate hard-liners on this issue. But when you said you would preserve the embargo as leverage, you sounded as if you were pandering to them. As you know, there is no evidence that any unilateral sanctions program anywhere in the world has ever been effective in changing the internal character of the target government. So I have to assume that you and your political advisers held back on the ultimate disposition of the embargo in order to secure Cuban-American votes. Mr. President, you won Florida without the votes of Cuban-American hard-liners. Because of massive voter registration drives in that state, registered Hispanic Democrats now outnumber Hispanic Republicans by 513,000 to 445,000. You won the state with the votes of 57 percent of Hispanics, up from 44 percent for John Kerry in 2004. In Miami-Dade County, 55 percent of Cuban Americans under 29 years old voted for you, while 84 percent of Cuban Americans over 65 years old voted for John McCain, following the national trend. And although 35 percent of Cuban Americans voted for you, a 10 percent increase over John Kerry's 2004 showing, it was the non-Cuban Hispanic vote and other votes across Florida, especially in the African-American community, that increased your margin enough to carry the state. These gains are less a result of the needle you threaded on American policy toward Cuba than on the strength of your overall platform and campaign. Your triangulated position on Cuba prevented those Cuban-American voters inclined to vote for you from voting against you and attracted first-time American voters. McCain still carried most Cuban-American votes.

In congressional elections, where three Democrats supporting only family travel challenged the three Cuban-American Republican seats in South Florida, all three lost to the incumbents by wide margins. Their races were less about Cuba than about the real issues working Americans face. Although the three Cuban-American Republican hard-liners have been safely reelected, they are now in the minority opposition. And with your victory in Florida the result of a constellation of non-Cuban-American votes, your Cuba policy need no longer defer to the Cuban-American political status quo of the last 50 years.

There are two Cuban-American Democrats in Congress, Senator Bob Menendez and Representative Albio Sires of New Jersey, who well understand that current policy toward Cuba has failed, and who, I believe, will support Cuban-American and people-to-people travel, as well as direct talks on issues of security, especially. They and their constituents will not support a full-blown elimination of the embargo. Although they may well voice their objections to openings beyond Cuban-American family travel and perhaps some humanitarian trade, they know that their case for granting one group of Americans a right denied to another will not hold up legally, or politically. They will be unable to stop the Democratic leadership in the Congress from pursuing a legislative agenda aimed at ultimately dismantling the embargo. But they will attempt to assure that any legislation aimed at relaxing sanctions is balanced by ample support for human rights and civil society in Cuba. It will be important that whatever initiatives along those lines they advocate are cleansed of the tainted democracy-promotion-regime-change ethos of recent memory. And even then, these programs are likely to remain highly politicized. Whatever their ultimate character, the U.S. Interest Section in Havana must become a proper vehicle for diplomacy and outreach to all Cubans rather than a conduit of cash aimed at inciting would-be anti-regime activists.

In that light, with respect to travel and trade sanctions, I recommend you take the steps your executive authority allows, and leave the rest to Congress. If, five to 10 years from now, Cuba is more pluralistic and more free, it will have been the result of Cuba's own choices. But by following the proposals outlined here, you will be the president of the United States who showed the political courage and foreign policy wisdom to create the external conditions that will have made possible such a long-elusive outcome.

Julia Sweig is the Nelson and David Rockefeller Senior Fellow and Director, Latin American Studies, Council on Foreign Relations. She is the author of the forthcoming book, Cuba: What Everyone Needs to Know.

More in Cuba

See all
Cohiba 55 Aniversario Hitting Market With Enormous Price Tag

Cohiba 55 Aniversario Hitting Market With Enormous Price Tag

In the immediate aftermath of Cuba’s sweeping price hikes, the new cigar will carry a price tag more …

May 20, 2022
U.S. Reversing Course On Cuba: More Flights, Fewer Restrictions, Easier Investment And Travel

U.S. Reversing Course On Cuba: More Flights, Fewer Restrictions, Easier Investment And Travel

In a substantive change in U.S. policy toward Cuba, the Biden administration announced that it will …

May 17, 2022
Habanos S.A. Sets Record With More Than $500 Million In Sales

Habanos S.A. Sets Record With More Than $500 Million In Sales

Habanos S.A. posted a record $568 million in sales last year, up 15 percent from 2020. 

May 12, 2022
$100 Cohibas Coming As Cuban Cigar Prices Going Up

$100 Cohibas Coming As Cuban Cigar Prices Going Up

Cuban cigars are about to get more expensive the world over.

May 10, 2022
Explosion At Cuba’s Hotel Saratoga

Explosion At Cuba’s Hotel Saratoga

Cuba’s Hotel Saratoga, a high-end property in one of the busiest and most famous areas of Havana, was …

May 6, 2022
Phoenicia: The Cuban Cigar Powerhouse

Phoenicia: The Cuban Cigar Powerhouse

Little known to American cigar lovers, Phoenicia Trading is one of the world’s largest distributors …

Apr 25, 2022