By nearly every available measure, Fidel Castro lived just a little too long. His was a death foretold by nearly everybody for decades, a demise anticipated for the political change it was widely assumed would surely follow. The prospect of Cuba without the man who turned it into a Soviet satellite so tantalized the U.S. government that its darker sectors set up a cottage industry aimed at hastening the day: according to a 1975 Senate investigation, the CIA set out plan after plan to assassinate Castro, most notoriously by poisoning a box of his favorite cigars. All any of it did was make him seem invincible–a swaggering dictator whose continued presence on the planet served as a rebuke to a Washington once so sure of its dominion over the hemisphere. The longer Castro lived, it seemed, the greater the legend grew.
But by the time Castro finally died, on Nov. 25, he had been out of power for a decade, and almost entirely overtaken by events–especially the cascade of changes that began in December 2014, when his kid brother and successor, Raúl, made peace with President Obama. Though Fidel grumped about trusting an archenemy in the rare speech and opinion column, the elder Castro was powerless to stop a U.S. ambassador from returning to the embassy on the Malecón, or to keep U.S. tourists from filing down the gangplank of cruise ships at Havana Harbor or to prevent Cubans clamoring once again for yanqui dollars. Three days after his death, the official mourning period essentially shuttered the country, yet did not delay the descent of American Airlines Flight 17 onto the runway of Havana’s José Martí International Airport. It was the first regularly scheduled U.S. airline flight to arrive in Havana in more than 50 years.
But it was fitting, in a way, that Castro’s death came just as U.S. President-elect Donald Trump was making the most fateful personnel choices of his Administration: Secretary of State and Secretary of Defense. A foreign policy novice, the tycoon will face far graver (and less settled) international questions than Havana after his Inauguration on Jan. 20. North Korea has both an erratic leader and nuclear weapons. Russia juggles a shrinking economy, an aggressive military and an expanding role in the Middle East. China is bracing for a threatened trade war, and Europe wonders if the transatlantic alliance that maintained peace for seven decades is about to be open to negotiation.
So little is clear that Castro’s departure took on the quality of a test case for the incoming leader of the new world. Castro’s death was announced around midnight, and hours passed with no word from the President-elect. Finally, at 5:08 a.m., it came, not a communiqué or diplomatic statement but, of course, a tweet. The terse message–“Fidel Castro is dead!”–only served to enhance interest in who might be coming aboard to school the new executive in the delicate and nuanced business of international affairs. The selection process was already under way, with the characteristic Trump fanfare. Having named arch-conservative supporters as National Security Adviser (General Michael Flynn), Attorney General (Senator Jeff Sessions) and CIA Director (Representative Mike Pompeo), the President-elect made it clear he was chiefly considering a handful of men for Secretary of State: Rudolph Giuliani, the former New York City mayor who had been one of the few prominent Republicans to champion his campaign, and former presidential candidate Mitt Romney, the most prominent Republican to condemn Trump on the campaign trail. Former CIA Director David Petraeus made a showing as well–“very impressed,” Trump tweeted after a meeting. Waiting in the wings, in case the other three fell short, was Tennessee Senator Bob Corker, whose chances kept improving as the days ticked by.
The business of selecting a Cabinet is by tradition a discreet one, a stately promenade that summons, more than any one individual, a sense of the greater calling of public service. Not this time. Trump’s candidates took turns running the gauntlet of reporters camped in the lobby of whatever Trump property the President-elect was currently occupying. Advisers offered counsel in person, if they were nearby, or on TV news, which they knew had Trump’s attention. Kellyanne Conway, who ran Trump’s campaign, took to ABC’s This Week, NBC’s Meet the Press and CNN’s State of the Union to kneecap Romney, saying his selection would infuriate Trump voters. The fact of the takedown was familiar enough to Beltway insiders, who are accustomed to decoding Sunday-morning television. But the method was sheer prime time, where much of the appeal of what the industry calls “unscripted” shows like The Bachelor is the public humiliation of the spurned contestant. Trump did this himself on The Apprentice.
“The thing that is really freaking people out is that Trump seems to be turning the high-profile Cabinet posts–State, Treasury, Defense–into a reality show,” says one longtime Washington veteran. “If he gets chosen, Mitt would instantly be an outsider, damaged goods and not part of Trump’s inner circle. So they’ve already hurt him. Whether [Conway] did what Trump wanted her to or not, we don’t know. But it doesn’t matter.”
Of course, unsettling official Washington–“draining the swamp,” as he put it on the campaign trail–is one of the things Trump was elected to do. But now the whole world is watching, and the lessons being absorbed may not be benign. Governments address one another in the elaborate, often deeply coded words of diplomatic language for a reason. The words may be verbose and often superfluous, but each is meant to matter. Misreading isn’t just a mistake; it can be a tragedy. In July 1990, Saddam Hussein infamously left a meeting with U.S. diplomat April Glaspie believing he had gotten the nod to invade Kuwait–which is exactly what he did, eight days later–all because of a misreading by one or both of what was being said.
The sea of ambiguity on which Trump’s policies float is already producing unease. The Mexican stock market is down amid fears about NAFTA. An emboldened Syrian President Bashar Assad is moving with Russian air cover to decimate rebel-held areas of Aleppo, forcing thousands of civilians to flee for their lives. And if the President-elect has been less than clear about his policy on Israel and the Palestinians, that alone emboldens the stronger side. After Trump’s election, a Jerusalem deputy mayor cleared the way for 7,000 previously on-hold homes for Jews on historically Arab land, “to exploit the change of guard in the USA,” he said.
The impulsive, twittery air of the Trump transition has done little to reassure a world that wonders: What happens if the billionaire addresses U.S. foreign policy from the White House in the same way he did on the campaign trail–that is, by the seat of the pants? As a GOP primary candidate, Trump stood out for his support of Obama’s decision to rekindle relations with Cuba, which had been ice-cold for half a century. “Fifty years is enough,” Trump said, while adding, “We should have made a better deal.” A year later, Trump named the terms: “Those demands are religious and political freedom for the Cuban people. And the freeing of political prisoners.”
Trump threatened that once he was sworn in, he would have the same executive authority to undo everything Obama has done to normalize relations with Cuba. Technically, he does. But experts both in Cuba and the U.S. warn that closing the opening would have consequences. Most immediately, it would revive the fortunes of Cuban hard-liners who lately have been losing ground inside the country’s closed system. Until Trump’s election, the same decline had been evident among the older Cuban Americans who for decades had dominated U.S. policy toward the island, a cadre that includes Mauricio Claver-Carone, who has been advising Trump on Cuba. A variety of reasons account for the softening, including the flow of Cubans and money between the island and the mainland, and the dying-out of elderly Cuban exiles who feel more strongly about the issue than their children. In Florida, only 54% of Cuban Americans voted for Trump.
Then there’s the odd logic of making the death of Castro–the architect of Cuba’s revolution–a moment to return to a Cold War footing. The opening to the U.S. is hugely popular with the Cuban people–97% supported the policy in an independent poll. Obama has 80% approval ratings in Cuba, nearly twice that of either of the Castros. The derelict Cuban economy is only slowly opening to foreign investment, including communications infrastructure, such as the Internet, that Obama argued will eventually empower the Cuban people. But Cubans are eager to go into business for themselves, and say they are counting on economic ties with the U.S. to stay afloat.
“Is Trump a change agent for Cuba, or by inflaming the relationship is he going to wake up and give a new life to the hard-liners in Cuba for whom Fidel is and was the leader?” asks Julia Sweig, author of Cuba: What Everyone Needs to Know. “Fidel off the stage means there’s a greater reform government.”
The calendar also favors change. Raúl Castro, who is 85, announced three years ago that he will step down in 2018. His designated successor would be the first non-Castro to lead the country since 1959: Miguel Díaz-Canel, 56, and a Politburo member since 1997, is described as an engineer with a common touch and enthusiasm for the Internet.
But hard-liners remain in large numbers, and some would welcome a reversion to a familiar posture of antagonism with an old foe, allowing the embattled Communist Party to appeal to the public on nationalist grounds. “Fidel is dead, but Fidelism is not,” one senior Cuban official tells TIME. “Fidel is more than a person. He is a state of mind. We are ready to face, as we have done in the past, all challenges.”
On this score, the Cubans certainly have some experience. “What can Mr. Trump do that we had not had before?” the official asks, speaking privately during the period of official mourning. “We are ready for anything and everything. He is again threatening us like the bully he is, but experience has taught us that we can stand against bullies. We will defend our way of doing things but foremost our sovereignty.”
As powerful as the President is, the realities of geography still apply–especially on Cuba. “Cuba is not that simple because first of all, it’s close: it’s 90 miles offshore,” says Pedro Freyre, a Miami attorney who advises international clients on doing business with Havana. “So if you do something misbegotten, the consequences are going to wash up offshore, as they have before. Any misstep by the United States could trigger another Mariel, and then you’re looking at another 100,000 people sleeping under bridges in Miami.”
So far it has been mostly tourist firms such as Airbnb and Carnival that have invested in Cuba, but U.S. phones now roam there and other sectors are interested. “We’re selling chickens and grains there from states that voted for Trump,” says Freyre. It’s only been two years, but in that time the political constituency on Cuba has grown far beyond Calle Ocho, the Miami street synonymous with anti-Castro activism. It’s now diverse both geographically and in terms of interest.
“This is not just a Miami-centric conversation,” says Daniel Restrepo, the former National Security Adviser on Latin America for Obama. “You now have U.S. air carriers and agriculture companies and hotel companies and cruise companies who are interested in engaging in business. You have a broader constituency than there was in the previous 50 years.”
A substantial section of Cuba’s government is counting on that as well. “There are facts that [Trump] cannot overlook, especially as a businessman,” a second senior Cuban official explained. “Interests, mutual interests have been created with the regularization of diplomatic ties. The machines are already running. We think that the two countries will win more as relations stabilize.”
On top of tourism–which took in an estimated 700,000 Americans who visited the island last year–the official named talks with the pharmaceutical industry and joint projects between the U.S. and Cuba on the environment and combatting the trafficking of drugs and of people. The two countries are also working more closely than ever in counterterrorism and Internet security, areas where there has long been cooperation but not the trust and facility that comes at the embassy level. “Collaboration has improved in ways people do not imagine,” the Cuban official said.
Cuban and American analysts alike assume that Trump will, in the end, approach Cuba the way he approaches so much else–as a businessman. His tweets refer to “a better deal,” and a deal is exactly what Obama brokered, privately: an exchange of prisoners paved the way for an exchange of ambassadors. Trump, as a hotelier and developer, would on the face of things seem more inclined to keep the deal going, rather than ratchet it back–not least because, by, say, scotching Marriott’s Four Points by Sheraton hotel in Havana, he might be seen as punishing a rival hotel chain and worsening his conflict-of-interest problem.
The challenge beyond Cuba is how few international problems lend themselves to such simple dealmaking. “He’s a transactional guy,” says Freyre. “But that transaction mind-set will face the reality of foreign policy.”
Which sometimes comes down to the events you don’t expect. And even a few you do.
“Every presidency is defined not by their agenda coming into office but by the crisis they encounter,” says Victor Cha, who was a National Security Adviser to George W. Bush and is now at Georgetown. “For President Bush, it was 9/11. For Trump, I think it will be North Korea’s ability to reach the United States homeland with a nuclear ICBM. Meanwhile, in South Korea, there is political paralysis that inhibits any coordination or early leader-to-leader contact between Trump and Park Geun-hye,” says Cha. “This is a train wreck in slow motion.”
That may be what much of the rest of the world is expecting a Trump foreign policy to look like. It’ll be up to him to prove them wrong.
–With reporting by DOLLY MASCAREÑAS/GUADALAJARA and MASSIMO CALABRESI and MICHAEL DUFFY/WASHINGTON
This appears in the December 12, 2016 issue of TIME.