Donald Trump and his Future Relationship with Latin America | PL Analysis

Julio C. Laínez
El Blog
Published in
9 min readDec 14, 2016
Many changes are in store for Cuba in the coming years after the death of Fidel Castro and his younger brother Raúl’s transfer of power to a new generation of post-revolutionaries led by Miguel Díaz-Canel.

This is the first installment of a three-part series.

The election of Donald Trump replaced preconceived notions about how presidential campaigns should comport themselves. It also sent shivers down the spines of political leaders in the capitals of Latin America. His unconventional ‘change campaign’ coupled with some of the most vindictive rhetoric aimed at many groups, including the Latino community, helped drive support from a loyal segment of white working class voters who felt overlooked by Democrats for many years. Not surprisingly, a clear and cogent vision for Latin America remained a mystery during the campaign, and continues to be a mystery now.

The death of Fidel Castro and the eminent retirement of his brother Raúl in 2018, on the other hand, have thrust Cuba into a much larger role in defining Trump’s foreign policy in the region. That being said, Castro’s death will not just have repercussions for U.S. foreign policy, but will also influence domestic U.S. policy as well considering the political engagement of the Cuban American community in South Florida.

Part I of this analysis piece will center on post-revolutionary Cuba and how the eventual transition from the Castro brothers presents a chance for the Trump administration to shape U.S.-Cuba policy in the near future. Parts II and III will be published later and will deal with Mexico and Central America, followed by the rest of South America.

Part I: A look back at post-revolutionary Cuba then and now after the death of Fidel

On November 25, Fidel Castro — who ruled Cuba with an iron fist from 1959 to 2006, when he ceded almost all control to his younger brother Raúl — died at 90. The elder Castro came to power after a revolución that ousted Fulgencio Batista with an initial force of 9,000 fighters, which included Ernesto “Che” Guevara, Raúl Castro, and Camilo Cienfuegos, who would later become the Héroe de Yaguajay, after the famous battle. Castro’s military campaign and romanticized vision of the revolution won the hearts and minds of the Cuban people fed up with the authoritative and repressive regime of Fulgencio Batista who was passively supported by the United States. “I’m glad [U.S.] Ambassador [to Cuba Arthur] Gardner approves of my government,” Batista would say after he organized a military coup to return himself to power, “but I wish he wouldn’t talk about it so much.”

After his revolution, Castro flirted with friendlier relations with the United States during his 11-day trip to New York in April of 1959, a scant three-and-a-half months after his ascendancy to power, but issues such as agrarian reform, and the reduction of the sugar import quota eventually soured relations. After his three-hour meeting with Castro, Vice President Nixon commented that Castro was “either incredibly naive about communism or under communist discipline — my guess is the former.”

“The one fact we can be sure of,” wrote Nixon in a memorandum after his meeting with Castro in 1959, “is that Fidel Castro has those indefinable qualities which make him a leader of men. Whatever we may think of him, he is going to be a great factor in the development of Cuba and very possibly in Latin American affairs generally.”

Back in Cuba, what began as a revolution against repression and gross human rights abuses, began to transform itself into the same dragon it had slayed. Castro not only lived a life of false austerity, but more importantly, betrayed the hope of millions of Cubans who saw in the revolution a vehicle for their hopes and dreams after the repressive dictatorship of Batista. Castro consolidated his grip on Cuba and began to transform a hopeful takeover into a repressive and authoritarian state by nationalizing U.S. business interests, banning land ownership, and cozying up to the Soviet Union.

The United States subsequently broke off diplomatic relations, supported an ill-fated invasion by Cuban exiles at the Bay of Pigs, and imposed a trade embargo. The invasion was a colossal failure and a boon politically for the regime. At the Alliance for Progress founding meeting in Punta del Este, Uruguay, in 1961, Che Guevara ‘thanked’ White House aide Richard Goodwin for the Bay of Pigs: “Their hold on the country had been a bit shaky,” recalled Goodwin in William LeoGrande and Peter Kornbluh’s masterful book Back Channel to Cuba: The Hidden History of Negotiations Between Washington and Havana, “but the invasion allowed the leadership to consolidate most of the major elements of the country around Fidel.” After the failed invasion, Cuba imprisoned many of the expats that fought in the sands of Playa Girón in the Bahía de Cochinos, and took the meta diplomatic efforts of negotiator James Donovan, who had negotiated the release of U-2 pilot Francis Gary Powers, to assure the safe return of the prisoners back to the United States. Donovan’s relationship with Fidel Castro was immortalized in an article that appeared in The Nation in 1963 titled “How Metadiplomacy Works: James Donovan and Castro,” which detailed Donovan’s herculean effort of securing the prisoners’ release as well as the departure of 3,500 relatives after the 1962 missile crisis.

Back channel communications between Cuba and the United States, however, continued through successive U.S. administrations and there were even small glimmers of hope for some sort of rapprochement a few times, including under the Ford administration. “A solution could be found if [Castro] is flexible,” quipped Secretary of State Henry Kissinger, “as far as I’m concerned, it is a question of domestic politics. We have to show something he’s doing, to justify the lifting [of the embargo].” Cuba’s incursions into Angola didn’t win them any favors, however, and nothing would come out of it. Presidents Carter, Reagan, Bush, Clinton, and Bush didn’t make much progress either.

Finally, in December 2014, under the auspices of Pope Francis and The Vatican, the Obama administration came to an understanding with Raúl Castro, essentially “changing a relationship frozen in time,” as Miami Herald reporter Mimi Whitefield would write. The agreement aimed to ease restrictions and begin the opening of the island after more than half a century of a failing U.S. policy. The news of the rapprochement between the two countries was met with jubilation in Cuba and most of the United States, but viewed with anger and suspicion among the older Cuban exile community in Miami. “To those who oppose the steps I’m announcing today, let me say that I respect your passion and share your commitment to liberty and democracy,” said President Obama. “The question is how we uphold that commitment. I do not believe we can keep doing the same thing for over five decades and expect a different result.”

Raúl Castro Ruz and President Barack Obama shake hands at the VII Summit of the Americas held in Panama City, Panama from April 10–11, 2015. Peru will host the VIII summit in 2018.

“The fifty years has shown that isolation has not worked,” continued Obama. “Neither the American nor Cuban people are well served by a rigid policy that is rooted in events that took place before most of us were born.” Cuba would also release U.S. Agency for International Development subcontractor Alan Gross, and 53 political prisoners. The United States, meanwhile, released three Cuban spies who were serving time for their connection to the 1996 shoot-down of two Brothers to the Rescue planes by a Cuban MiG29. After the incident, the U.S. Congress passed the Helms-Burton Act which strengthened and codified the embargo. It remains firmly in place to this day.

Fast-forward to 2016 and Cuba finds itself at a crossroads. The passing of Fidel Castro on November 25th reminded everyone of the fragility of life and the eventual end of the Castros’ grip on the island. The slow and methodical transition which began in 2006 when Fidel ceded almost all control to his brother Raúl, will replace the ‘vieja guardia’ with a new generation born after the revolution. The death of Castro means very little for immediate U.S.-Cuba policy, since he had been essentially retired for ten years, but has major repercussions in the medium and longer term for Cuba.

The death comes three years after Raúl Castro announced that he would retire in February of 2018, and look after a “gradual transfer” of key roles to “new generations.” In the mid-term, I see Cuba taking a ‘wait and see’ approach in regards to the incoming administration. They’ve been at it long enough to know what a change in administration means for U.S.-Cuba policy and will give time for the dust to settle. However, if they feel like they cannot possibly work with a President Trump, I fully expect Raúl Castro, followed by his eventual successor, to take a hardline approach with typical “anti-imperialist” rhetoric, further retrenching themselves into an age-old playbook.

But who will lead the new Cuba after Raúl retires? It is likely that the new Cuba will be led by Miguel Díaz-Canel, an electrical engineer and former Minister of Higher Education. He is currently First Vice President of the Council of State and Ministers, a role he’s had since 2013. Little else is known about Díaz-Canel, however reports indicate he is a technocrat with good managerial skills. According to Arturo López Levy, lecturer at the University of Texas-Rio Grande Valley and former analyst with the Cuban government, Díaz-Canel worked as an intermediary between the Cuban central government and the military, a crucial relationship to watch beginning in 2018.

Raúl Castro’s transition could represent an important opening for Trump to build on a relationship with the new Cuban leader through which he could strategically coax the new Cuban government into further negotiations on political prisoners, human rights, compensation for seized U.S. property, and other vexing matters. Cuba will also have a long list of demands to bring to the table, not least of which is the $833 billion in reparations for the “human and economic damage” they claim the embargo has caused the island, per a State Department source to the New York Times.

Nevertheless, the Trump administration has an opportunity to make a mark and build on the inroads the Obama administration has made in Cuba. This makes the choice of Rex Tillerson for Secretary of State one of the most consequential choices in recent years. For Donald Trump, individuals like Mitt Romney or Sen. Bob Corker would have added gravitas and balanced out his early recalcitrant choices of Stephen Bannon as chief White House strategist and Gen. Michael Flynn as national security advisor, so the choice of Tillerson is even more puzzling. It is also perplexing in its face and its symbolism as Tillerson believes in man-made climate change, and also has supported the Paris climate agreement in the past, positions that the president-elect clearly did not share in the campaign.

In regards to Cuba, however, there’s nothing in the public sphere pertaining to that thorny issue, so his confirmation hearings will be an opportunity for the country to understand where he falls on Cuba policy per se. As a businessman, I would imagine that he will have a difficult time reconciling Trump’s anti-Castro, anti-rapprochement rhetoric with the more nuanced approach of the Obama administration, something the business community favors immensely. We will be paying close attention to those hearings in January.

Make no mistake, the prospect of rolling back advances in Cuba relations is not just bad policy in and of itself, but will have negative repercussions across Latin America. Already the business community is extremely anxious about the prospect of a policy reversal and is currently courting Trump to continue Obama’s course with Cuba. Trump’s business instincts will be pitted against political expediency, a tug-of-war that will test the new president in more ways than one.

Will Miguel Díaz-Canel lead a new Cuba to build on the advancements made under President Obama and Raúl Castro with the Trump White House beginning in 2018 or are we looking at renewed frozen relations?

One person likely to forcefully intervene, be it successfully or not, is Representative Mario Díaz-Balart (R-FL25), a vocal anti-Castro legislator who cruised to re-election on November 8 winning 62% of the vote. The following day he tweeted: “Cuban Americans soundly rejected Obama’s failed policy of appeasing the Castro brothers.” Then on November 14, he reiterated his point by again tweeting about Cuba: “Pres [sic] Obama said his legacy was on the ballot. He was right. Looking forward to U.S.-Cuba policy that puts US interest + freedom first. #Cuba.” Rep. Díaz-Balart is already using Trump’s favorite modus operandi to prepare what will be a full-throttled lobbying effort to reverse course on Cuba.

Another individual to keep an eye on is Mauricio Claver-Carone. Named to the Trump transition team for the Department of the Treasury, Claver-Carone has been one of President Obama’s harshest critics on Cuba, and will no doubt lobby for hawkish appointments in regards to Cuba policy at Treasury. Whether or not he will have an official role in the incoming administration remains to be seen, however. These will be the people who will help the new president decide the fate of Latin America’s priority level and breadth of focus.

However, until the dust settles and his administration is in place, Trump’s vision for Cuba and the region as a whole will remain as unpredictable as his temperament.

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Julio C. Laínez
El Blog
Writer for

Deputy Dir for Leg Affairs @TransportWorker . Proud former LD for @TeamMoulton and staffer for @SenatorReid . Writes about politics, policy, sports & tech.