United States relations with Cuba have been fraught with misunderstanding and conflict from day one because politics has bested pragmatism. Cuba is Latin America’s oldest dictatorship and relations with the U.S. have been frozen in time, until now. President Obama initiated a policy of engagement and diplomatic rapprochement with Cuba last December — some 54 years after bilateral relations were severed. The reason is pragmatism: Engagement benefits the Cuban people and serves America’s economic and strategic interests. The history of U.S.-Cuban relations proves “engagement,” as Obama argued recently, “is a more powerful force than isolation.” The five-decade-old U.S.-sponsored hemispheric policy of isolating Cuba — a relic of the Cold War — has failed, as has the leaky economic embargo imposed in 1961, the same year of the disastrous Bay of Pigs invasion by CIA-supported Cuban exiles. The ill-advised policy precipitated a nuclear confrontation in the 1962 Cuban Missile Crisis.

The goal of exclusion and economic warfare has been regime change — the defeat of the 1959 Cuban Revolution and the ouster of Fidel and Raúl. Castro’s Marxist revolution was to be delegitimized and the regime destabilized lest there be contagion and other Latin American countries become copycats and challenge U.S. interests. Useful for domestic electoral politics, the containment and rollback strategy has backfired. Although sanctions have succeeded in impoverishing and isolating the Cuban people, the Castro brothers’ regime has persisted and achieved legitimacy, not only in the eyes of most of the hemisphere’s leaders and citizens, but also internationally. Pope John Paul II visited Cuba in January 1998, urging “the world to open up to Cuba, and Cuba to open up to the world.” Fidel Castro, instead of being reviled in global public opinion, especially the Global South, is a living icon of revolutionary chutzpah, the defiant David to the U.S. Goliath! The 33 heads of state in the hemisphere demanded that Cuba be invited to the VII Summit of the Americas in Panama in April. For the first time since the founding of the summit in 1994, Latin America’s opposition to Washington’s exclusion policy did not overshadow the meeting. The act of Raúl Castro and Obama shaking hands (although not for the first time) was symbolic: Cuba was on its way back into the hemispheric fold!
The road towards normalization promises to be slow and rocky, and politics threatens to overwhelm pragmatism once again. A first step will be to review and rescind Cuba’s outdated status as a state sponsor of terrorism, which did happen on May 29. Cuba was added to the (often politicized) list in 1982, charged with aiding Latin American insurgencies. But Cuba’s proactive revolutionary internationalism ended decades ago. The world is far different now, and as Secretary of State John Kerry observed, “the United States has had, and continues to have, significant concerns and disagreements with a wide range of Cuba’s policies and actions, these concerns and disagreements fall outside the criteria for designation as a State Sponsor of Terrorism.” And in recent decades both Castro brothers have strongly denounced terrorism.
What have been the history and the causes of this half-century estrangement? And what are the lessons to be learned? Certainly one ironic lesson is that often leaders and countries that became our enemies might have become our friends. The love-hate relationship between the United States and Cuba has a tortured history. The United States initially wanted to buy Cuba from Spain and the U.S. Congress heatedly debated whether to annex Cuba outright as a state of the union (giving its people citizenship rights) or maintain the island as a U.S. protectorate. Pragmatism (and racism) won the debate: “The people of Cuba, by reason of race and characteristic, cannot be easily assimilated by us,” opined Senator Orville H. Platt. In the 1898 Spanish-American War, the United States liberated Cuba from Spain’s colonial rule, but then militarily occupied the island until 1902. Independence was conditional: the U.S. Congress imposed the Platt Amendment to the new Cuban Constitution, which gave the United States the right to intervene to “maintain government adequate for the protection of life, property, and individual liberty.”
The United States did intervene directly and indirectly. Teddy Roosevelt sent U.S. troops in 1906, “so angry with that infernal little Cuban republic that I would like to wipe its people off the face of the earth.” If only the Cubans would behave themselves. There were U.S. Governorships in 1906-1909, and military expeditions in 1912 and 1917-1922, and U.S. Ambassadors exercised outsized influence (interference) until 1959. Although billed as interventions for democracy, the protection and advancement of U.S. economic and geopolitical interests remained paramount. And despite President Woodrow Wilson’s claim that the United States was the friend and champion of constitutional government in the Americas, a cozy relationship developed with Latin dictators. In Cuba, our man was Fulgencio Batista, president or powerbroker from 1933 to 1959. In 1934, President Franklin Roosevelt supported Batista’s “sergeants’ revolt” and instituted his “Good Neighbor” policy revoking the Platt Amendment and promising no more interventions.

However, the amendment had already been unilaterally abrogated during the nationalistic 1933 revolution of Ramón Grau San Martín against dictator Gerardo Machado (1925-1933), with the cry, “Cuba for Cubans.” But the Grau government’s reforms were dangerous and U.S. Ambassador Sumner Welles feared it “minimizing any form of American influence in Cuba.” Welles, therefore, conspired with Batista to overthrow the reforming government; all subsequent efforts at reform were quashed as well — until 1959. Everyone knows the story of the rag-tag group of exiles that land in Cuba on July 26, 1956, launch the Sierra Maestra guerrilla insurgency and celebrate quick victory less than three years later.
Here then lies a second important foreign policy lesson, learned somewhat late but famously stated by President John F. Kennedy (who launched the Bay of Pigs invasion and then the Alliance for Progress in the aftermath of the Cuban Revolution): “Those who make peaceful revolution impossible make violent revolution inevitable.” The question of whether it is moral for the United States to roll back a country’s reforms or revolution aside, it is a self-defeating policy in the long run. A third important lesson logically follows: The most pragmatic and effective way to encourage democratic change with radical regimes is to engage them constructively. Otherwise, the confrontation challenges a people’s right to determine their own political destiny and a country’s sovereignty, and invites a powerful nationalistic backlash.
The Eisenhower administration, in an atypical departure from past U.S. policies towards revolutionary regimes, recognized the Cuban Revolution and the government of President Fidel Castro on January 7, 1959 — six days after the 26th of July guerrillas triumphantly marched into Havana. Despite the confusion of U.S. policy in these early days, Washington seemed to realize that this was a critical time to influence relations, which were not yet fully defined. The belief was that Castro would have to cut a deal; even a Cuban revolutionary had his price! But things went wrong, nevertheless. And the debate of whether it was inevitable, whether Castro was a communist all along, and who was most at fault is only partially instructive.
In April 1959, Castro visits the United States but Eisenhower will not meet with him, and in March 1960 the president authorizes the CIA to train Cuban exiles for an invasion. Advised by the State Department, U.S. oil companies refuse to refine oil purchased from Soviet Russia; Castro nationalizes the refineries. President Eisenhower then cancels the Cuban sugar quota, half of the entire Cuban crop and mainstay of their economy. Cuba then expropriates some $1 billion in U.S.-owned properties. The United States raises the Cuba issue in the Organization of American States (but receives only tepid support), and imposes a partial embargo. Washington breaks off diplomatic relations in January 1961. The Bay of Pigs invasion follows in April and Castro declares that he is a Marxist-Leninist, denounces “Yankee imperialism,” and becomes a Soviet ally. A third and fourth lesson emerges from all this: U.S. policy cannot evolve effectively in a tug-of-war among the president, congress, national security and intelligence agencies, and powerful interest groups. And: If you extend a fist, don’t expect a handshake. (And there have been at least eight attempts to overthrow Fidel Castro!)
Cuba only radicalized further and exported revolutionary internationalism in the 1970s, sending tens of thousands of combat troops to Angola in 1975 and Ethiopia in 1978. President Ford proposed normalizing relations if Cuba withdrew troops from Angola, and President Carter opened an interest section in Havana. But in the aftermath of the Nicaraguan Revolution in 1979 and Salvadoran insurgency in the early 1980s, President Reagan tightened the embargo and established Radio Martí.
By 1989, another potential thaw developed: Castro offered to help in fighting drug trafficking, and President Bush, Sr. (while on the campaign trail) talked of normalizing relations if the Cuban regime reformed and stopped human rights abuses. But it was also the beginning of the end of the Soviet Union, whose aid had propped up Castro, and Panama’s General Noriega, who had helped circumvent the embargo. The U.S. Congress instead tightened the embargo further in 1990 and 1992, and in 1996 passed the Helms-Burton Act (the Cuban Liberty and Democratic Solidarity Act), which extended the sanctions regime to all global trade with, and international investment in, Cuba. Policymakers expected Castro to fall, but he didn’t. Lesson here: Sanctions are a double-edged sword that make leaders more, not less, resistant to change, and can consolidate their rule.

Since then, cycles of loosening and tightening sanctions and travel restrictions have continued. In 2000, congressional legislation permitted Cuba to purchase food and medicine, but in 2004 the embargo and travel restrictions were tightened again. Obama recently relaxed travel and trade restrictions. The American business community and the international community increasingly oppose the embargo and diplomatic isolation of Cuba as counterproductive, a political rather than pragmatic policy. And younger Cuban-Americans largely share this view. Cuba is becoming a major buyer of U.S. agricultural goods, and has implemented limited economic reforms, and seeks greater access to the U.S. market. Nevertheless, the embargo remains in place, its repeal conditioned on regime change, or in blunter terms, the overthrow of Cuba’s socialist system. As America seeks to normalize relations with Cuba this presents a fundamental inconsistency and contradiction — more politics, less pragmatism. The United States has removed North Korea from the terrorist list and has diplomatic and trade relations with China and Vietnam. Therefore, the final lesson of U.S.-Cuban relations (to quote President Obama): One can’t “keep doing the same thing for over five decades and expect a different result.” Foreign policy needs to be pragmatic and adaptive; doing what works and abandoning what doesn’t.
And it is not just about Cuba. U.S. relations with Latin America and the world at large have gained a boost with Obama’s constructive engagement with Cuba. The outdated isolation of Cuba has been one of the main reasons that U.S. diplomacy in the region has been losing ground, uniting governments of all political persuasions, and on the defensive in international forums. The 2015 Summit of the Americas in Panama was the most amicable and forwarding looking in a time when relations with major Latin countries have become frayed. It provided an important opportunity not only for the Castro regime, but also for Cuban civil society to participate and protest for change. In regional opinion polls Cuba has achieved record goodwill with its export of doctors while hemispheric opinion of the United States has deteriorated. Obama had enough of U.S. bashing and off-the-cuff history lessons of past abuses, and affirmed, “Cuba is not a threat to the United States.”
Major opinions polls agree. The December 2014 CNN/ORC Poll found that 53 percent of respondents viewed Cuba as “no threat at all” and 21 percent as “just a slight threat”; and only 26 percent of a “very serious” to “moderately serious threat” (7 percent and 19 percent respectively). And when asked whether they favored or opposed reestablishing U.S. diplomatic relations with Cuba, 63 percent favored and 33 percent opposed, about the same percentage distributions as in 2009 and 2006 surveys (71 percent to 27 percent, and 62 percent to 29 percent respectively). And 55 percent of respondents supported ending the embargo with 40 percent opposed. And most telling, 67 percent favored “change current policy” that maintained travel restrictions over 32 percent “continue current policy.”
Critics still hope for radical regime change and worry that détente with Cuba will deliver a triumph to the Castro brothers. But it is not simple or that black and white. The real triumph will be for the Cuban people who will have greater opportunity to mold their own destiny. Moreover, regime change is dangerous. In September 2011 in the wake of the Arab Spring, Obama noted the enormous changes in the Middle East and hopefully described Cuba as “this small island that is a throwback to the 60s.” Since, the Middle East remains convulsed in turmoil and violence with conditions in most countries worse than before the revolts. Perhaps this is another final lesson. With the Castros on the wane, the diplomatic transition will be the best way for them to go, slowly fading into history as the respective governments on the island and the mainland catch up with popular opinion. More importantly, the new policy will revitalize Washington’s influence and credibility in the hemisphere, increasingly being courted by rival powers like China, and soften if not end the anti-imperialist refrain that has dominated intra-regional relations and provided left-populists with anti-American capital. The triumph of pragmatism over politics is not just about Cuba, but also what most benefits U.S. national interests.
Image credits: Graphics by Kristina Ramos/FORWARD Florida.