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.