Shadow Government

A front-row seat to the Republicans' debate over foreign policy, including their critique of the Biden administration.

Can Obama’s One-Sided Cuba Deal Be Salvaged?

The White House misplayed its strong hand, but negotiations are just getting started. Here's what Washington should be asking for.


For almost a week, the Obama administration has been basking in the glow of editorial page plaudits (at least the editorial pages of the New York Times and Granma) for its gambit in moving to normalize relations with Cuba. But now that some time has passed, it is worth taking a closer look at the nature of the deal itself, and what the next steps might be.

Spoiler alert: the Cuba deal is not a halcyon moment in the annals of American diplomacy.

In its negotiations with Cuba, the Obama administration made two fundamental mistakes. First, the White House failed to realize that it holds a much stronger negotiating hand than Havana. The Castro regime is at arguably its weakest and most vulnerable point in over 50 years, as it faces the loss of its petroleum patronage from a fragile Venezuela buffeted by $60 per barrel oil prices. This is a dictatorship desperate to survive.

Yet instead of capitalizing on America’s substantial leverage to gain meaningful Cuban concessions, the Obama administration made its second mistake of communicating to the Castro regime that Washington was more desperate for a deal than Havana. The savvy Cubans realized this. The result is an agreement in which the United States grants to Havana substantial political and economic advantages, while Havana concedes pretty much nothing. (This is setting aside the prisoner swap, which is a separate matter and could have been undertaken as a confidence-building measure prior to diplomatic negotiations on the overall relationship).

There may be a case for amending U.S. policy toward Cuba – as Walter Mead astutely points out in the American Interest, the Castro regime has cynically used the embargo as an instrument in clinging to power – but the timing, manner, and especially nature of the Obama administration’s new policy is a major setback for American interests, and for the interests of the Cuban people. It is a failure of diplomacy.

Judging by President Obama’s comparisons to past American policy shifts towards China and Vietnam, it is also a failure to understand history. In both cases, China and Vietnam had undertaken substantial reforms in their foreign and economic policies before the United States normalized the respective bilateral relationships. It was based on these demonstrated improvements that the United States could reciprocate with diplomatic upgrades and closer economic ties.

In the case of China, Nixon’s historic 1972 visit cemented China’s status as a strategic partner aligned with the U.S. in the Cold War contest against the Soviet Union. Then in 1978, Deng Xiaoping launched his historic economic reforms. The geopolitical shift in China’s external behavior, and Deng’s internal reforms, both occurred prior to America’s official normalization of the U.S.-China relationship (though the normalization negotiations were undertaken as Deng’s reforms were unfolding). Likewise with Vietnam, which launched its pivotal Doi Moi economic liberalization reforms in 1986, nearly a decade before the Clinton administration normalized the U.S.-Vietnam relationship.

In jarring contrast, Cuba has not undertaken any similar reforms in either its external behavior or its internal political and economic structure. If anything, the Castro regime seems intent on pocketing the Obama administration’s concessions as yet another lifeline to maintain its hold on power and keep its dictatorship alive. As Yale historian and Cuban exile Carlos Eire points out in an eloquent remonstrance to the new policy:

While much attention has been paid to President Obama’s Cuba policy speech, hardly any has been paid to dictator Raúl Castro’s shorter speech, broadcast in Cuba at exactly the same time. In his spiteful address, the unelected ruler of Cuba said that he would accept President Obama’s gesture of good will “without renouncing a single one of our principles.”

The White House has dug a deep diplomatic hole for the United States, but more negotiations lie ahead to implement the new Cuba policy, so all opportunities are not yet lost. In the spirit of the holidays and Shadow Government’s tradition of offering constructive criticism, here are some specific suggestions for steps the United States should seek from Cuba:

  • Cuba itself may not be much of a security threat to the United States, but the Castro regime has happily offered the island as a prime intelligence collection platform for our geopolitical rivals China and Russia. The White House should demand that Havana expel all Chinese and Russian intelligence agents and listening posts before normalization. (One precedent for this is Egypt under Anwar Sadat, who expelled all Soviet military advisors from Egypt in 1972, laying the groundwork for an eventual rapprochement with the United States).
  • The White House trumpeted Cuba’s apparent willingness to release 53 political prisoners, a shameful token in light of the reported over 8,000 prisoners of conscience incarcerated in Cuba. As candidate Obama himself said in 2008, the White House should demand the release of all prisoners of conscience before normalization. (For those Castro apologists who downplay Havana’s repression, the comparison with Vietnam is revealing: Vietnam has a population of 92 million people and about 70 political prisoners. Cuba has a population of 11 million people and over 8,000 political prisoners).
  • Cuba still gives sanctuary to over 70 fugitives who fled American justice, including murderers and domestic terrorists. The White House should demand the extradition of every American fugitive before normalization.
  • President Obama’s speech unfortunately implied that the American embargo has prevented the Cuban people from accessing the Internet, when in fact it is the Cuban government that bans private internet access. The White House should demand that Havana permit unfettered Internet access for every Cuban citizen before normalization.

These are just a start. There are many other issues that should be on the negotiating table as well, especially economic reforms such as currency conversion and access, and substantial increases in private property rights.

At this juncture, Cuba has successfully parlayed its weakest hand in a half-century into a strategic win – not because of the Castro regime’s negotiating genius, but because of its good fortune in having a desperate and diplomatically maladroit counterpart in the Obama administration. But this is just the opening chapter, and as the White House moves into the implementation negotiations, and as Congress exercises its authorities in oversight, funding, and economic relations, there remain many areas to press for improvements from Havana.

After all, even the Castro brothers are sometimes willing to make reforms. This week it bears recalling that in 1997 Fidel agreed to lift his three-decades old ban on Christmas.

Mario Tama/Getty Images

Will Inboden is the executive director of the William P. Clements, Jr. Center for History, Strategy, and Statecraft at the University of Texas-Austin. He also serves as an associate professor at the LBJ School of Public Affairs and as a distinguished scholar at the Robert S. Strauss Center for International Security and Law.