Fidel Castro
Tracks Credit: Marcelo Montecino/Flickr

At his rallies, Fidel Castro was fond of bellowing, “Socialismo o muerte!”—Socialism or death! Death finally caught up with the dictator last November, and Cuban socialism’s days are likely numbered as well. The Cuban people soon will enter the post-Castro period after President Raúl Castro steps down in two years, as he has promised. What comes after that is anyone’s guess. To be able to have any influence in this transition period, Washington will need to identify which Cubans are in the best position to steer events.

As the United States goes through its own transition, the Trump administration will have to decide whether to continue President Obama’s normalization of relations with Cuba or to slam on the brakes, demanding that Havana cease oppression of political dissidents and pursue concrete steps toward democratization.

In our approach to Cuba, we first have to understand what makes official Cuba tick. The reality is that the Communist Party may indeed be history, but one major player is likely not only to stick around, but to keep calling the shots. That player is the Fuerzas Armadas Revolucionarias (FAR), Cuba’s armed forces. The FAR play a role outsized to their numbers, now around 90,000, down from double that during the Cold War years.

The FAR are widely considered to be Cuba’s best-managed and stablest government organization and are held in respect by Cubans generally. They run the economy and control politics. Since he succeeded his brother as president eight years ago, Raúl, who had commanded the FAR since the revolution, has expanded their role. More than half of the Communist Party’s Politburo members have a military background, while the Council of Ministers is likewise dominated by active-duty or retired FAR officers.

The Cuban military controls 60 percent of Cuba’s economy and takes in 40 percent of foreign exchange revenue. The FAR’s so-called “entrepreneur soldiers” manage a wide docket that includes sugar and cigar production, tourism, information technology, and aviation. One in five Cuban workers is employed by the FAR’s holding company, GAESA, which is headed by Raúl’s son-in-law, Luis Alberto Rodríguez López-Callejas, an army brigadier who speaks English with a proper upper-class British accent.

I got to know Cuban military officers as the State Department’s representative at monthly military meetings on “The Line”—the border between U.S. and Cuban territory—at Guantánamo Bay Naval Base. I found them to be professional, constructive, and amiable. The general who headed the Cuban side even offered to find me “a beautiful Cuban wife,” which I politely declined, having a beautiful American wife already. For years our respective militaries built up a modest level of mutual trust through collaboration on migration matters, sea-air rescue, counternarcotics, oil pollution response, and firefighting. Once, on flying into the naval base, the pilot of our small aircraft had to perform a corkscrew landing to avoid clouds of billowing black smoke kicked up by a brush fire sparked by exploded land mines on the Cuban side as firefighters from both sides of the fence worked together to put out the blaze. Since normalization under Obama, bilateral contacts and cooperation have been growing.

Occasionally, indications surface of tension between old-guard Fidelista officers and younger technocrat/entrepreneur officers. The future lies with the latter group, who are eager to build trust with Washington in hopes the United States won’t “pull an Iraq” on them by encouraging the FAR’s dismantlement in a postcommunist new order and opening the gates to chaos. In order to have the most impact on change, the U.S. needs to get to know and cultivate the pro-reform elements within the FAR.

I visited scores of Cuban families in their homes as a U.S. diplomat with the task of monitoring the human rights conditions of those who tried and failed to flee their country. I was struck by how Cubans always had one eye on the dinner table and one eye on the clock—meeting the daily challenge of how to feed their families while patiently awaiting the time when they could join the globalization wave. Their fretting fed the Cuban proclivity for dark humor. One example:

Student: “Before the revolution, the government took this country to the edge of an economic abyss.”

Teacher: “And after the revolution?”

Student: “Now our government has taken a big step forward.”

Change has been slow in coming. After retiring in 2008, Fidel hovered over Cuba as an éminence grise, second-guessing his younger brother’s decisions. While Fidel grudgingly went along with Raúl’s cautious economic reforms, he had little to say about rapprochement other than that he didn’t trust the U.S. Now that his big brother is gone, will Raúl feel freer to liberalize the Cuban economy and accelerate normalization? If so, time is running out. The eighty-five-year-old revolutionary has said he will retire in 2018. His designated successor, First Vice President Miguel Díaz-Canel Bermúdez, is a dour Marxist apparatchik with questionable political staying power. For the first time since the 1959 revolution, Cuba will not be led by a Castro. How will the U.S. deal with it?

Trump has issued conflicting signals. He told CNN earlier this year that he would “probably” maintain diplomatic relations with Cuba, but added vaguely that he would insist on “much better deals than we’re making.” But he took a tougher line in a campaign stop in Miami several weeks ago, saying, “All of the concessions Barack Obama has granted the Castro regime were done through executive order, which means the next president can reverse them, and that I will do unless the Castro regime meets our demands.” Vice President–elect Mike Pence repeated that position on Twitter, asserting that Trump would rescind President Obama’s executive orders without “real political and religious freedom” in Cuba.

With the news of Fidel’s death, Trump issued a statement denouncing his legacy “of firing squads, theft, unimaginable suffering, poverty and the denial of fundamental human rights.” That tough talk caters to the anti-Castro political right, which includes many, mainly older, Cuban Americans. Polls show, however, that a large majority of Americans and now most Cuban Americans favor normalization.

So does the U.S. business community. According to the U.S. Agriculture Coalition for Cuba (USACC), Cuba, which imports 80 percent of its food, is a $1.7 billion market for agricultural products. Last year, the U.S. Commerce Department issued approvals for business transactions worth $4.3 billion, up by a third from the previous year. Tourism will doubtless surge in the years ahead regardless of the fifty-six-year-old official ban that is still in place. Remittances from the United States, estimated at $3 billion for 2015, play a significant role in Cuba’s state-controlled economy.

USACC, whose membership includes agricultural conglomerates Cargill, Smithfield Foods, and Sun-Maid, is devoting serious money to lobby Congress to lift the embargo and fully normalize relations. So is the U.S. Chamber of Commerce. The Cuba Opportunity Summit will hold its third convention next spring at NASDAQ headquarters to explore expanded business opportunities with Cuba. Tickets go for between $995 and $1,695, and interest in the first two conventions was so strong that applicants had to be waitlisted.

How will Trump respond to this kind of commercial momentum? Will we see the pro–tourism development, hotel-building Trump, or the right-wing appeaser Trump? American leverage can be a carrot or a stick. The latter approach was pursued by ten presidents, starting with Dwight Eisenhower, and accomplished little more than allowing the Castros to use the U.S. as a scapegoat for Cuba’s mismanaged economy. The former approach, however, enables the U.S. to gain leverage by being involved with Cuban society at multiple levels, ranging from trade and investment to cooperation on migration and law enforcement to people-to-people contacts. It was easier for Havana to thumb its nose at American interests when there was near-zero U.S. economic and commercial involvement in the island. Major American involvement in Cuba’s economy, in particular, will deepen Cuba’s integration into the global economy, raising the stakes for both sides and tempering political relations. The Trump administration needs to realize that allowing Cuba policy to be haunted by Fidel Castro’s ghost is a bad idea. American business interests will resist it, and both the Cuban and American people deserve better.

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Follow James on Twitter @JamesLBruno. James Bruno is a Washington Monthly contributing writer and former U.S. diplomat. Read his blog, DIPLO DENIZEN, and follow him on Twitter @JamesLBruno. The opinions and characterizations in this article are those of the author, and do not necessarily represent official positions of the U.S. government.