Ivan Alvarado / Reuters

There’s something deeply ironic about the circumstances of Fidel Castro’s death on Friday: The Cuban dictator survived all manner of U.S. assassination plots—the poison pills, the lethal bacterial powders, the mafiosi—when U.S.-Cuban relations were at their lowest point, only to pass away when the relationship between the two countries was at its highest point in nearly six decades. Fidel, as far as I know, did not die of a heart broken by his brother Raul’s recent reconciliation with the imperialists to the north. But his demise at age 90, with his cronies still in power and his one-party police state still intact, calls for reflection on what, if anything, all those years of antagonism and estrangement accomplished.

Instead, the president-elect of the United States is threatening a return to the days of isolating Cuba economically and diplomatically. Campaigning this fall in Miami, home to many anti-Castro Cuban Americans, Donald Trump promised to “stand with the Cuban people in their fight against communist oppression,” criticizing the “concessions” that Barack Obama had made to the Castros. This week, Trump warned that if the Cuban government “is unwilling to make a better deal for the Cuban people, the Cuban/American people and the U.S. as a whole,” he would reverse Obama’s efforts to restore relations, which have included the reopening of embassies in both countries and the easing of restrictions on Americans traveling to and doing business with Cuba.

Reince Priebus, Trump’s incoming chief of staff, elaborated on what a “better deal” might look like. “There is nothing wrong with talking to people,” he told Fox News, but Trump isn’t prepared to have an “open and free” relationship with Cuba until the Cuban government makes progress in ending political repression, opening markets, protecting freedom of religion, and releasing political prisoners.

This characterization of Obama’s overtures to Cuba—as a bad deal that Trump will renegotiate—misses a critical point of the president’s policy. Initially, Obama almost sounded like Trump in portraying his Cuba policy as a kind of deal. “If you [the Cuban regime] take significant steps toward democracy, beginning with the freeing of all political prisoners, we will take steps to begin normalizing relations,” Obama vowed as a presidential candidate in 2008.

As president, however, Obama began normalizing relations with Cuba even though the Cuban government never took significant steps toward democracy, beyond releasing some political prisoners. This decision could be attributed to Obama’s weakness as a negotiator or his desperation to strike a deal. But it can also be interpreted as the logical conclusion of a principle Obama introduced in his inaugural address in 2009: “To those who cling to power through corruption and deceit and the silencing of dissent, know that you are on the wrong side of history, but that we will extend a hand if you are willing to unclench your fist.”

Through his outreach to Cuba, Iran, and Burma, Obama has been making a subtle, sustained argument that, when opportunities arise, talking to hostile governments can be more prudent and more productive than not talking to them, even if those adversaries are corrupt, deceitful, and intolerant of dissent. Put another way: Trump says Cuba hasn’t yet earned diplomatic relations with the United States; Obama, it seems, has come to believe that diplomatic relations are worth pursuing even if Cuba doesn’t “deserve” it. “Sanctions without outreach, condemnation without discussion, can carry forward only a crippling status quo,” Obama said in accepting the Nobel Peace Prize in 2009. “No repressive regime can move down a new path unless it has the choice of an open door.”

This may be a controversial concept in the United States, but it’s not in other countries. As Geoffrey Wiseman, a professor of international relations at the University of Southern California, told me earlier this year, the United States has a long tradition of isolating adversarial governments unless they meet certain conditions, while seeking to engage the people ruled by those governments as a counterweight to the adversary. (Hence why U.S. politicians denounce the oppressive Castro regime but ally themselves with the oppressed Cuban people.) Many European countries take a different approach: They recognize states—not governments, which come and go in various forms—and they try to change the behavior of adversarial states through continuous diplomatic dialogue. Wiseman’s research indicates that the “isolation of adversarial states, more often than not, does not work” in achieving the objectives of the isolationist policy.

Even in the United States, it’s very common for the government to maintain ties with countries where political and religious freedom are severely restricted—the rationale Trump has given for halting Obama’s opening to Cuba. Here, for example, is a list of countries labeled “not free” by Freedom House that enjoy full diplomatic relations with America. (Iran and North Korea, which also fall into the “not free” category but don’t have diplomatic relations with the United States, pose far greater threats to the U.S. than Cuba does today.)

  • Somalia
  • Eritrea
  • Uzbekistan
  • Turkmenistan
  • Sudan
  • Central African Republic
  • Equatorial Guinea
  • Saudi Arabia
  • Laos
  • Bahrain
  • South Sudan
  • Ethiopia
  • Azerbaijan
  • China
  • Tajikistan
  • Belarus
  • Yemen
  • Swaziland
  • The Gambia
  • Burundi
  • United Arab Emirates
  • Vietnam
  • Chad
  • Russia
  • Kazakhstan
  • Afghanistan
  • Angola
  • Cameroon
  • Rwanda
  • Oman
  • Democratic Republic of Congo
  • Egypt
  • Iraq
  • Qatar
  • Republic of Congo
  • Djibouti
  • Burma
  • Brunei
  • Mauritania
  • Cambodia
  • Thailand
  • Gabon
  • Algeria
  • Jordan
  • Uganda

What’s unique about Cuba, of course, is its bitter, Cold War-inflected history with the United States: the Bay of Pigs invasion, U.S. trade embargo, Cuban Missile Crisis, Mariel boatlift, Brothers to the Rescue debacle, and on and on. But here too, the history is more complicated than is typically acknowledged. Raul Castro and Barack Obama are far from the first people to consider whether Cuba and the United States have more to gain from cultivating relations than from cutting them.

In the months after Fidel Castro’s revolution in 1959, for example, Philip Bonsal, the last U.S. ambassador in Havana, made a compelling case for the United States to remain engaged with the island despite Castro’s anti-American rhetoric and flirtations with the Russians. But the Eisenhower administration, alarmed by the prospect of a Soviet beachhead just off America’s shores, quickly abandoned Bonsal’s approach. Castro repeatedly reached out to U.S. presidents with proposals for improving the relationship. “I now believe that this hostility between Cuba and the United States is both unnatural and unnecessary,” he said in a message to Lyndon Johnson in 1964. In Washington, plans for an opening to Cuba surfaced as early as the Kennedy administration, when the president and his advisers pursued an “accommodation” with Castro as an alternative to what they referred to, euphemistically, as their “nasty” policies. In a sign of John F. Kennedy’s conflicted approach, a U.S. emissary met with Castro to discuss negotiations on the same day that a CIA officer delivered a poison pen to a Cuban agent for use against Castro. That very same day, November 22, 1963, Kennedy was gunned down in Dallas. Henry Kissinger and Jimmy Carter also explored ways to normalize relations, but to no avail. Politics, circumstance, and the demands of the Cold War got in the way.

Barack Obama, a child of the Cold War but not a prisoner to it, has done more than any U.S. president since Dwight Eisenhower to establish dialogue with Cuba. More than that, however, he has challenged Cubans and Americans to rethink policies he considers at odds with 21st-century realities. The counterargument to Obama’s pledge to extend a hand to unclenched fists is something Rosa Maria Paya, a Cuban democracy activist, once told me. Quoting her father, a dissident who died mysteriously in Cuba, she said, “If you are going to extend a helping hand to the Cuban people, you should first ask for the Cuban people to have their hands untied.”

But even Paya didn’t oppose Obama’s diplomatic and commercial engagement with Cuba. What she wanted was for U.S. leaders to continue demanding democracy and human rights for Cubans as part of the new dialogue. “Cubans are not less than Americans,” Paya said. “Why do we have to sit down and wait for a king to die?”

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