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Obama’s Cuba Doctrine

... and why Trump should keep it.

Ronald Reagan famously confronted the Soviet Union with “evil empire” rhetoric and a dramatic military buildup. But he also emphasized energetic diplomacy and free citizen contact, as he explained to a gathering in the White House’s East Room in June 1984.

To establish a “better working relationship” with Moscow, he would seek to open new consulates and ease visa procedures, convene high-level military dialogues, and revive cooperation in health, trade, environmental protection, housing, and agriculture.

Reagan praised private organizations that promoted citizen exchanges, declaring that “civilized people everywhere have a stake in keeping contacts, communication, and creativity as broad, deep, and free as possible.” Government best contributes to this, he said, “by not standing in the way.” He decried Soviet action in Afghanistan and repression at home, but argued that “we must be careful in reacting to actions by the Soviet Government not to take out our indignations on those not responsible. And that’s why I feel that we should broaden opportunities for Americans and Soviet citizens to get to know each other better.”

For this, Reagan became the hero of the Cold War.

And for following this same playbook when he took relations with Cuba out of the deep freeze two years ago, President Obama won the support of three in four Americans. He leaves in place a sober, realistic strategy that President Trump would do well to keep.


From the 1990s until the Obama administration, the heart of U.S. strategy toward post-Soviet Cuba was essentially to pursue a goal of war—regime change—without military force, and with means completely inadequate to such an ambitious end. It was based on the assumptions that the socialist government was on the verge of collapse, that its hard-currency balances were the key to its survival, and that it could be brought down through economic sanctions and support to Cuban dissidents.

Lawmakers tightened the embargo in 1992 and 1996 in the hope of pushing Cuba over the brink. But the strategy’s fullest expression came under the George W. Bush administration, which tightened sanctions to the maximum, going so far as to limit the contents of gift parcels that Cuban Americans sent to their relatives and to make it illegal for them to visit their relatives more than once every three years. Bush spent up to $44 million per year to support dissidents and to persuade Cubans to join them.

Needless to say, neither the sanctions nor the dissidents nor the Bush efforts to prime the political pump did the trick.

As a candidate in 2008, Barack Obama called for a new approach to Cuba that would replace “tough talk that never yields results” with diplomacy and engagement. In his first term, he eased restrictions on travel and remittances, mainly for Cuban Americans.

Then, in his sixth year, he announced that “the United States of America is changing its relationship with the people of Cuba.” His strategy was later set forth in a rare unclassified Presidential Policy Directive.

In this document, Obama stated that “we will not pursue regime change in Cuba” and set a new goal: “to help the Cuban people to achieve a better future for themselves” and to work with Cuba on “regional challenges such as climate change, disease, and illicit trafficking.” The  strategy sought a “prosperous, stable Cuba.” “It does not serve America’s interests, or the Cuban people, to try to push Cuba toward collapse,” Obama declared.

Most important, the Obama strategy deemed that “endogenous changes under way in Cuba offer opportunities to advance U.S. interests.” Those changes include booming entrepreneurship, a private sector that now employs one in four Cuban workers, expanding Internet access, and new laws that allow Cubans to travel abroad and to buy and sell residential real estate. Obama, unafraid to recognize positive steps taken by a reforming Raul Castro, saw an opportunity for American visitors and companies to help those changes advance.


Eighteen months of secret talks between emissaries of Presidents Obama and Castro led to the unveiling of a new relationship on one dramatic day: December 17, 2014.

Before dawn, planes crossed the Florida Straits to carry out a classic piece of Cold War business—a prisoner swap that sprung intelligence agents (three of theirs, one of ours) and one U.S. contractor from jail and sent them home. At noon, the presidents announced that they would restore diplomatic ties and work to normalize relations.

By the following summer, embassies reopened in Washington and Havana. The governments struck agreements on the environment, law enforcement, agriculture, health, mail service, and other matters, and they started regular talks on human rights, economic policy, migration, and settlement of the claims filed by U.S. companies whose property was expropriated.

The most tangible change is an explosion of citizen contact, driven by bold acts of deregulation that virtually erased the requirement that Americans obtain licenses from the federal government to travel to Cuba.

About a half-million Americans are visiting Cuba annually, and Cuban data record more than 1,200 academic, cultural, and other exchanges during 2016. U.S. universities are sending more than 2,000 students each year to Cuba, and State Department educational programs are bringing Cuban students and professionals to the United States.

The Obama deregulation also fostered commerce. U.S. airlines have regular flights to ten Cuban airports; four U.S. cellular carriers provide roaming service in Cuba; Google signed an agreement to improve Cuba’s Internet; Marriott is operating hotels; a New York research institution is collaborating in the development of a Cuban cancer remedy; Airbnb serves 4,000 bed-and-breakfast operators in 40 Cuban cities; and companies are exploring deals in energy, infrastructure, health, financial services, construction equipment, and exports of many other goods and services. With remittances deregulated, large numbers of Cuban Americans are investing in private family businesses and buying houses in partnership with their relatives in Cuba.

The new policies did not erase enduring disputes, but they undeniably created a new dynamic. Americans, once scarce in Havana, now flood the place—roaming colonial streets, filling private restaurants, holding exchanges with Cubans in places of worship, businesses, artists’ studios, farms, and private homes. Cuban-Americans are repairing family connections, and many send their children to spend the summer. Negotiators in Cuban ministries and enterprises are dealing for the first time with serious American business proposals, evaluating both the business merits and the political implications of the presence of companies from a country that a century ago dominated their economy.

President Obama visited Havana in March 2016, the first American President to do so since Calvin Coolidge arrived on the battleship Texas in 1928. Obama met Cuban officials; discussed business with private entrepreneurs and representatives of state enterprises in a modern brewpub facing Havana Bay; addressed the Cuban people from the stage of a 19th-century theater (the latter two events broadcast on Cuban television); took his family to dinner at a back-street private restaurant; and spent two hours with Cuban dissidents.

Obama came, he said in his main address, “to bury the last remnant of the Cold War in the Americas.” He noted close historical and cultural ties and acknowledged that in other eras, Americans came to Cuba “to liberate, but also to exert control over Cuba.” He praised Cuba’s educational system and its deployment of doctors to work in needy areas around the world. He disavowed any intention “to impose change on Cuba,” but expressed hope for Cuban citizens to be able to reach their full potential. Even if the U.S. embargo were to vanish, he argued, Cubans are held back by limits on hiring, business licensing, “the free and open exchange of ideas,” and Internet access. These are among the keys to “sustainable prosperity in the 21st century,” he said, and they are entirely “up to you.” He invoked the right of peoples “to choose their governments in free and democratic elections.”

Obama’s visit was a hit among most, but not all, Cubans. Weeks after his departure, the foreign minister told a Communist Party congress that it was “an attack at the core of our political vision, our history, our culture, and our symbols.” Brushing off Obama’s embrace of Cuba’s private sector, he insisted that the real “guarantee” of its existence “is precisely socialism and the Cuban revolution.” It was thus registered that Cuba remains on guard against imperialism—but U.S.-Cuba diplomacy continued apace, then and since.

Obama did not achieve normalized relations with Cuba, a goal that in the economic sphere alone must await repeal of the U.S. embargo. Cuba insists, reasonably enough, that it also means ending the U.S. presence at the Guantanamo naval base, the last vestige of the settlement imposed on a weakened Cuba at the end of its war of independence, which we call the Spanish-American War.

What Obama did was to normalize Cuba relations within the context of American foreign policy. With engagement replacing isolation as the guiding principle, he treated Cuba like other communist countries. He promoted two-way travel as was done across Eastern European borders, enshrined in the Helsinki accords, extended diplomatic recognition as with communist Vietnam, and enabled commerce as has been the case with China for decades in spite of its human rights practices.

The result is the first Cuba policy that makes strategic sense since the Cold War ended. Ends and means were put in alignment. Grandiose regime-change plans were replaced by engagement that has tangible impact. U.S. policies were rooted in realistic assessments of conditions in Cuba and the opportunities they offer, and U.S. citizen contacts were valued as an asset rather than a risk to be policed.

Obama refused to allow himself to be measured solely by his actions toward Cuba’s dissidents, opting instead to connect with the Cuban people as a whole and their government. This includes the vast number of Cubans, including many Communist Party members, who want change but bristle at foreign efforts to bring it about. These are nationalists who view their government as legitimate and want it to be the vehicle for change. Regime-change talk makes them tune out. Obama did not win them over by being polite to Cuban officials, advocating repeal of the embargo, and recognizing facts about past U.S. conduct. But he created a path for communication with those citizens who may matter most in Cuba’s political future.


What will President Trump do with this strategy?

In his inaugural address he declared that the United States will not “seek to impose our way of life on anyone.” His White House website defined “America first foreign policy” by going straight to the taproot of American anti-interventionist thought: “The world must know that we do not go abroad in search of enemies, that we are always happy when old enemies become friends, and when old friends become allies.”

On Cuba, Trump made his gut instincts known on several occasions during his campaign. “Fifty years is enough,” he said last September in reference to Obama’s new policy. “I think it’s fine, but we should have made a better deal.” “I think Cuba has a certain potential and I think it’s okay to bring Cuba into the fold,” he said last March.

But in late October he changed tack; when accepting the endorsement of Bay of Pigs veterans in Miami, he said he would present Cuba with “demands” for political liberalization and reverse Obama’s executive actions if those demands are not met. Later he tweeted: “If Cuba is unwilling to make a better deal for the Cuban people, the Cuban/American people and the U.S. as a whole, I will terminate deal.”

Many Trump advisers share his original preference for engagement. White House adviser Anthony Scaramucci traveled to Havana last year and planned to create a Cuba investment fund. Deputy national-security adviser K.T. McFarland endorsed Obama’s opening to Cuba because it denies Russia and China a free field to “develop strong bilateral and economic—and possibly military relations” with Havana. Secretary of state nominee Rex Tillerson has opposed economic sanctions as ineffective when they are imposed on U.S. companies only.

Sen. Marco Rubio and others advise Trump to revive the Bush policies, but these are hardly a “better deal” for anyone. Will President Trump really want to restore a regulatory bureaucracy to police American travel and re-impose limits on Cuban-American family visits—and thereby harm the Cuban entrepreneurs who thrive on U.S. customers? Will he close diplomatic channels that allow the United States to press its positions on human rights, economic policies, and expropriation claims? Will he force U.S. businesses to abandon projects in Cuba? Will he stop joint research on cancer or diabetes remedies because success might mean that a Cuban company makes money?

In practical terms, the “better deal” lies in building on the Obama policies to reap greater benefits from engagement:

Farm exports. Since 2000, it has been legal for Americans to export agricultural products to Cuba. Sales peaked in 2008 at $810 million, but are now about one-fourth that amount, in part because U.S. banks are barred by law from offering normal, private financing for these exports. If Congress and the administration allow private financing, U.S. exporters will improve their competitive position and reclaim lost market share.

Security and justice. Obama did Trump a favor by ending the open-door immigration policy that applied to Cubans only. This will end a flow of tens of thousands of undocumented migrants each year and enhance border security. It will also require cooperation with Cuban authorities to return deportees. Trump’s effort to secure the southern border—and to fight drugs, terrorism, and illegal migration—should build on Obama’s initial steps to build relationships with the defense and security agencies of Cuba, the largest land mass in the Caribbean. While he is at it, Trump should press for return of fugitives from U.S. justice and be prepared to hear demands that he turn over persons residing in the United States who committed terrorism against Cuban civilians.

Claims. U.S. companies and individuals have filed nearly 6,000 claims for properties expropriated by Cuba. Talks have barely begun on these and on Cuba’s claims for damages from CIA attacks in the 1960s. A deadlock is likely given Cuba’s inability to pay and the U.S.’s refusal to acknowledge, much less compensate for, past covert actions. Trump could turn this problem into an opportunity by telling claimants that if they wish to negotiate new business deals in Cuba, he will license those deals if they include satisfaction of property claims. And he could allow claimants to sell their claims to persons who would wish to try their luck in negotiating deals of their own. The result would be to get money into the hands of some claimants, increase commercial activity, and reduce the amount to be settled one day in a government-to-government negotiation.

Push export opportunities. Obama policies opened the door to U.S. exports—to Cuba’s half-million entrepreneurs, to private farmers and cooperatives, and to supply Cuba with infrastructure, renewable energy, and more modern telecommunications. Trump could work profitably to make this opportunity bear fruit—including by pressing Cuba to take necessary steps such as creating wholesale markets for its private sector.

In February 2018, Raul Castro will leave Cuba’s presidency. A next-generation figure, not an octogenarian comrade from the 1959 revolution, will likely replace him. New leaders will need to earn legitimacy, one Cuban journalist writes, “by representing the interests of a pluralistic society, not through historical gratitude.”

President Trump will soon choose how to approach our 11 million neighbors in Cuba—through confident engagement, or a return to policies first conceived in 1960.

He should trust his gut.

Philip Peters is president of the Cuba Research Center in Alexandria, Va., and serves as a consultant to U.S. companies in Cuba.