A year ago, when U.S. President Barack Obama and Cuban President Raúl Castro awkwardly shook hands at Nelson Mandela’s memorial service, social media erupted with speculation about what the gesture might mean. Most Cuba watchers were skeptical, and they cautioned against reading too much into the encounter. But as Wednesday’s historic announcement of a new direction in U.S.-Cuban policy made clear, sometimes a handshake is more than a just a handshake.

Over the last 18 months, it turns out, U.S. and Cuban officials conducted secret high-level dialogues that were hosted by Canada and the Vatican. At the top of the Americans’ agenda was Alan Gross, a USAID subcontractor arrested in Cuba in 2009 for his role in a covert program to increase Internet access on the island. Cuban negotiators, meanwhile, hoped to secure the remaining members of the Cuban Five— intelligence agents who had been imprisoned in the United States since the late 1990s. Many observers had called for a swap, but the Obama administration had long refused to countenance what it considered an unequal exchange. In the end, the face-saving solution was for Cuba to unilaterally release Gross on humanitarian grounds and the United States to trade the three Cubans for an unknown U.S. intelligence officer. The timing of the announcement, coinciding both with Hanukkah (Gross is Jewish) and the feast of Saint Lazarus (syncretized in Afro-Cuban religions with the deity Babalu Ayé, widely associated with healing) could not have been more auspicious.

What remains unclear is how negotiations over Gross gave way to broader discussions culminating in a commitment to restore full diplomatic ties. Just a week ago, Cubaphiles reeled when the Associated Press again exposed USAID’s blundering democracy promotion programs on the island. The latest in their yearlong series of reports focused on efforts to amplify the antigovernment potential of the Cuban hip-hop group Los Aldeanos (without the artists’ participation). The U.S. Treasury Department’s Office of Foreign Assets Control, moreover, had just announced the newest in a series of whopping fines meted out against international banks doing business with Havana. To be sure, calls for policy change—none more prominent of late than the New York Times’—had become louder. But considering years of accumulated distrust, not to mention Cuba’s perennially low status on the foreign policy totem pole, few expected a speech so bold or a diplomatic shift so abrupt. 

It is important, however, to appreciate what this is not. The embargo—the bulk of it, anyway—remains in place. New openings for trade are the most significant since total sanctions were put in place in 1962. Yet it will be impossible to say just how quickly, and broadly, economic links between the two countries will grow until the U.S. Treasury and Commerce Departments release new versions of the Cuban Assets Control and Export Administration regulations. Obama and the Cuban government deserve credit for delinking, for the first time, diplomatic status from full commercial ties. Still, the path from strengthened political relations to complete normalization is long and fraught. Advocates of U.S. policy change may yet see a number of bumps in the road. And many Cubans, eager to quickly reap the benefits of a new era, might have to moderate their expectations.


Obama is not the first U.S. president to attempt restoring full diplomatic relations with Cuba. Jimmy Carter did, and much earlier in his administration. In Carter’s case, however, the extent of that commitment, and the failed negotiations behind it, remained largely confidential. With Wednesday’s announcements, the U.S. and Cuban governments have opted for a different strategy. Although previous talks transpired out of the public eye, future efforts to turn a new leaf will take place under unceasing media scrutiny. Stated expectations that formal embassies will be opened in a matter of months suggest that the process is already well on its way.

Other notable historical differences made this momentum possible. In the past, Cuba had made full removal of the embargo a condition for negotiations about diplomatic ties. In practice, furtive talks had generally taken on a tit-for-tat dynamic. In late 1962, for instance, Kennedy emissary James Donovan, an American lawyer and Commander in the United States Navy Reserve, secured the release of Bay of Pigs prisoners for $53 million in foodstuffs and medicine. Yet broad incrementalism—in which each side was expected to make gradual, reciprocal gestures—always failed. Thus, Henry Kissinger’s proposal of a step-by-step “package deal” during the Ford administration foundered when Cuba sent troops to Angola. This time around, the executive in both countries opted for a bold stroke that simultaneously left core issues unresolved. Reconciling, perhaps, with the fact that the embargo has been deeply codified in U.S. law since 1996, both sides thought it was wise to settle on the politically possible rather than the politically perfect. 

The spoilers of earlier periods are also conspicuously absent from today’s bilateral landscape. Conspiracy theorists have long accused Havana—and former leader Fidel Castro in particular—of not really wanting better relations with the United States, always spitting in the Americans’ eyes precisely at the wrong moment. During the Carter years, for instance, Cuba’s refusal to budge over its military and anticolonial commitments in Africa, rightly or wrongly, derailed the incipient rapprochement then underway. Today, Fidel is absent from the scene, and since the crippling post-Soviet crisis of the 1990s, Cuba’s international involvements have assumed a predominantly humanitarian footing. In the United States, with Miami’s pro-embargo political power on the wane and Latin American governments pressuring Washington and Havana to make a deal, there was simply less room to walk away.


The devil, of course, will be in the details. With full embassy status, practical diplomatic collaboration on issues such as counternarcotics, environmental protection, and disaster relief may proceed with few hurdles. Increased economic ties, on the other hand—especially with Congress unlikely to ditch the embargo whole hog—will not. As it is, the specific, strategic holes that the Obama administration has poked in trade restrictions, already a kind of bureaucratic Swiss cheese, may leave some critics of U.S. policy wanting more. Still, if the State Department opts to no longer designate Cuba a state sponsor of terrorism, as is expected, third-country banks will face less U.S. scrutiny when they do business with the island. 

Carefully calibrated to promote “independence from the Cuban state,” new direct commerce between the United States and Cuba will be geared, first and foremost, toward private sector expansion in agriculture and the urban small-business community. This focus is politically astute, albeit cautious. It echoes the arguments of moderate Cuban-American organizations such as the Cuba Study Group and, more recently, #Cubanow, which have been aggressively promoting “principled” rather than unchecked engagement. Still, just what kind of red tape will be wrapped around these transactions, how they will be facilitated, and how the Cuban state will respond have not yet been articulated. (By contrast, in the area of telecommunications, it appears that U.S. providers may gain increased legal cover to engage directly with the Cuban state.) Cryptically, Obama mentioned a Cuban commitment to “provide more Internet access to its citizens.” But again, what that means in practical terms remains to be seen, particularly considering the Cuban government’s anxieties about antigovernment viewpoints. 

Another complication is that Obama must continue to thread a very delicate ideological needle. On the one hand, he has fulfilled his pledge from early on in his administration to take U.S.-Cuban relations in a “new direction.” Nonetheless, in his remarks on Wednesday he also doubled down, rhetorically at least, on the United States’ commitment to democracy and human rights. Full diplomatic relations position the United States to raise its concerns in these areas more directly, and effectively, with Cuban leaders. Yet even if the White House seeks to pivot away from the kind of sloppy, irresponsible democracy promotion programs that got Gross in trouble in the first place, Congress may continue funding them, and the Cuban state is not likely to approve.

Finally, on the home front, critics opposed to even minimal policy change are already eager to gum up the works. Presumptive Republican presidential candidate Marco Rubio, the senator from Florida, was seething long before Obama even uttered a word. Pledging to block the confirmation of any proposed U.S. ambassador to Cuba from his new position as chair of the Senate Subcommittee on Western Hemisphere Affairs, he could make the journey from Wednesday’s announcement to a full-ranking diplomatic presence in Havana a politically unpleasant one indeed.


Sadly, somewhat lost in the shuffle thus far have been the diverse reactions of Cubans in the United States and across the island. U.S. national news channels predictably flocked to the Little Havana restaurant Versailles, long Miami’s capital of exile political chatter and guava pastries. Outside, defenders of the hard-line approach had gathered to express their disapproval of Obama’s “treason.” In neighborhoods like Hialeah, however—populated by some of the more than half million Cubans who have arrived in the United States since 1995—sentiments tended to reflect a practical concern for loved ones on the island. “This is a big step,” one Facebook commenter wrote. “The people of Cuba are the only ones who get screwed by those trying to take down the Castros from Miami, [where exiles can] eat meat and live the good life.” 

On the island, meanwhile, the popular jubilation reported in the international media soon may be tempered by the reality that announced measures fall short of the full monty. Initially, some seemed to think the bloqueo (the blockade, Cuba’s preferred term for the embargo) had been entirely lifted. But state media venues have focused on the return of the three Cuban agents above all. Seeking to calibrate expectations, on Saturday, Raul Castro emphasized in a televised address that the battle against the embargo will be “long and difficult." For the time being, expect to see more of this message—“el bloqueo está igualito,” the blockade remains the same, as one state website still has it—lest the elimination of the U.S. bogeyman place instant pressure on the Cuban government to jump-start its own stalled reforms.

That pressure is exactly what many proponents of the policy changes are hoping to see and what some in Cuba, whether out of self-preservation or genuine fear of the unknown, will attempt to resist. Then again, reshuffled relations with the United States, even imperfectly so, may give internal Cuban reformers—the genuine and the opportunists looking to make a buck—greater space to make their case. The difficulty of forecasting the outcome highlights the importance of improving policymakers’ access to and knowledge of Cuba’s internal politics. 

The agreement reached between the Obama administration and the Cuban government is by any measure historic, necessary, and overdue. Even many critics of the Castro regime recognize as much, albeit with resignation. Yet as the diplomatic rubber hits the road and Cuba continues its precarious transition to a mixed economy with rising inequalities, old disputes may take on new forms. “No es fácil” (It’s not easy), Obama said in his speech, quoting a common Cuban response to Spartan conditions on the island. Walking the diplomatic tightrope the president has proposed—let alone predicting what the island’s future holds for its long-suffering citizens—won’t be either.

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