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Negotiation By Tweet: The Uncertain Future of U.S.-Cuba Relations

After the announcement of Fidel Castro’s death on November 26, 2016, President Barack Obama sent a message to the Cuban people highlighting his administration’s efforts to improve relations between the United States and Cuba. “History will record and judge the enormous impact of this singular figure on the people and world around him…[T]he Cuban people must know that they have a friend and partner in the United States of America,” Obama said.

President-Elect Donald Trump took a different tack, tweeting simply, “Fidel Castro is dead!”

The following Monday, as the first U.S. direct commercial flight in over 50 years landed in Havana, Mr. Trump 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.” It is unclear what he means by the “deal.” President Obama’s relaxation of restrictions on Cuba is not part of a single deal. Rather, the President’s decision to increase engagement and shift policy toward the island nation has been implemented through a gradual series of Presidential Executive Orders, regulatory changes, and shifts in licensing policy.

Mr. Trump’s threat to terminate the “deal” might be read as a threat to reverse the steps the Obama administration has taken to ease travel and trade restrictions on Cuba. That threat has created a great deal of uncertainty for the future of U.S.-Cuba relations. During his campaign, Mr. Trump sent mixed signals about his approach on Cuba. In September 2015, Mr. Trump reportedly commented that “the concept of opening Cuba is fine.” His stance hardened closer to the election (as he fought for votes in the key electoral state of Florida), reportedly saying that he would close the newly opened U.S. Embassy in Havana and undo President Obama’s policies on Cuba.

Other influences may tend to harden Mr. Trump’s views further. His choice of Reince Priebus has a reputation as a Cuba hawk, as do influential members of the Republican Congressional delegation, including Marco Rubio and Ted Cruz.  Mr. Trump’s choice to head the National Security Council, Michael Flynn, has written that he sees Cuba as a country “allied with” Radical Islamists in a war against the United States.

Theoretically, undoing President Obama’s efforts would be easy for the new Trump administration. There is no legal barrier to reversing most or all of the Obama administration’s Cuba initiatives.

On the other hand, it is somewhat possible that the businessman in President-elect Trump could influence his views on Cuba, especially considering that his own organization reportedly investigated business opportunities in the Cuban hospitality sector as recently as six months ago. Since hospitality is one of the major sectors benefitting from Obama administration’s Cuba policies, it might provide fertile ground for further opening of the relationship.

There may be a possible approach lying between normalization and retrenchment. As noted by the US-Cuba Trade and Economic Council, Mr. Trump may choose to require that the Cuban government meet certain requirements as conditions to continuing the existing initiatives. Such conditions might include concrete steps on human rights. At the same time, enforcement of existing restrictions (which are many) could be beefed up through allocations to the chronically underfunded and understaffed Office of Foreign Assets Control within the U.S. Department of Treasury. But negotiating this middle path will be delicate. The Cuban leadership is extremely sensitive to criticism of its human rights record, but there are small signs of movement. For example, when President Obama visited the island in March 2016, he met personally with dissidents critical of both Castro and the United States. And Fox News reported after Fidel Castro’s death that Raul Castro’s regime has moved away from the worst abuses, including executions of dissidents and long-term sentences of political prisoners. But according to the same report, under the Raoul Castro regime, harassment and short-term detention reportedly continues to be used to disrupt the activities of dissident groups. Navigating those issues will place high demands on the diplomatic skills of Mr. Trump’s administration.

According to a recent Pew Research poll, there is broad approval across party lines for reestablishing diplomatic relations with Cuba and ending the embargo. Many sectors of the American business community would likely oppose rolling back President Obama’s changes, which have broken down economic and social barriers between the United States and Cuba. Travel to Cuba is immensely popular. Many companies have invested millions to enter the Cuban market, with the U.S. government’s authorization. As White House Press Secretary Josh Earnest argued, “unrolling” Obama’s policy is “just not as simple as one tweet might make it seem.” But this may not be enough to sway Mr. Trump.

For American businesses exploring opportunities in Cuba, it is important to be mindful that the next administration is likely to freeze any expansion of Cuba initiatives, at least while the new President sorts out his priorities. In the best case, existing policies might be made contingent on Cuba meeting certain human rights and other objectives important to the new President. Some of the more permissive Obama administration policies could be rescinded, and there may be increased enforcement by OFAC of the restrictions that remain. We also expect that after Inauguration Day, January 20, 2017, work on pending OFAC license applications is likely to be frozen until a clear agenda is set. While the uncertainty is unsettling, we will continue to look to a future, as President Obama stated, “in which the relationship between our two countries is defined not by our differences but by the many things that we share as neighbors and friends – bonds of family, culture, commerce, and common humanity.”

Copyright © 2017, Sheppard Mullin Richter & Hampton LLP.

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About this Author

J. Scott Maberry, Lawyer, Sheppard Mullin, International Trade, Trade Practice
Partner

Mr. Maberry is an International Trade partner in the Government Contracts, Investigations & International Trade Practice Group in the firm's Washington, D.C. office.

Areas of Practice

Mr. Maberry's expertise includes counseling and litigation in export controls, the Foreign Corrupt Practices Act (FCPA), anti-terrorism, economic sanctions, anti-boycott controls, and Customs.  He also represents clients in negotiations and dispute resolution under the World Trade Organization (WTO), North American Free Trade Agreement (NAFTA), and other multilateral and...

202-469-4975
Fatema Merchant, international, trade, Lawyer, Sheppard Mullin
Associate

Fatema Merchant is an associate in the Government Contracts, Investigations & International Trade Practice Group in the firm's Washington, D.C. office.

Fatema’s practice focuses on investigations and compliance counseling related to international trade laws.  She has extensive experience with U.S. Foreign Corrupt Practices Act and U.S.-Sanctioned Countries investigations, compliance, due diligence, and training.  Fatema also advises clients on compliance with International Traffic in Arms Regulations, Export Administration Regulations, Customs and Anti-Money Laundering regulations.  At Sheppard Mullin, she serves on the D.C. Diversity Working Group, Recruiting Committee, and is co-chair of the DC women lawyers’ group.  Fatema also serves on the pro bono committee and is actively involved in various pro bono matters, including preparing asylum applications and working with students at American University to seek resettlement for Iraqi refugees as part of the Iraqi Refugee Assistance Program.   

202-469-4930