When America’s geopolitical interests became a Cuban-American expectation of belonging.
I’m sure Cuban Americans feel a bit betrayed these days — if not a bit less American.
After a 68 percent majority of likely Cuban-American voters supported President Trump’s return to the Big Chair, about 8,000 Cuban nationals have been deported from the US.
Sure, deporting Cubans — for example — to African nations can seem odd.
I hinted at seeing a bigger story in a September Tano: “something bigger’s been deported.”
So it’s time to move past the Cubans-got-burned social media memes and dig into some history aspiring Cuban Americans may have overlooked: their privileged track to permanent resident status — or perhaps citizenship — was considered a given for decades.
Until it wasn’t.
There’s plenty to unpack. Let’s look at this betrayal in three movements.
Movement 1: From Migrant to “Exceptional” Migrant
Comparing the Cuban and Haitian experiences, for example, during the 1960s–70s will give you a sense of how exceptional Cubans were made to feel.
Sure, Cuba beats Haiti in the proximity-to-Florida test.
But aspiring Cuban Americans had something Haitians could almost never even speak of: “Freedom Flights” to America, sponsored by the US Government as a Cold-War thumb in Fidel Castro’s communist eye, and the 1966 Cuban Adjustment Act passed by Congress that made permanent residency easier for Cubans for the same geopolitical reasons.
Meanwhile, plenty of Haitians had similar reasons to escape Papa Doc for the same access to Lady Liberty’s promises, but didn’t have nearly the same kind of US sponsorship.
In fact, here’s a 1974 memo from the US Embassy in Haiti that acknowledges the difference in treatment between Cuban and Haitian migrants and suggests that if the US ever lifts its trade and diplomatic sanctions against Cuba, “the [State] Department might consider requesting Congress to drop or modify the special legislation on Cuban refugees to ensure equality of treatment to economic refugees from all countries.”
The Migration Policy Institute reports that 66% of Cuban immigrants were naturalized citizens in 2021, compared with 53% of immigrants overall.
Movement 2: Exceptional Cubans — Terms and Conditions Apply
The Soviet Union implodes and America wins the Cold War in 1991. No one thought Cuban migrant exceptionalism in the 90s seemed like an outdated propaganda flex?
And then a really interesting transition happened along the way: Cuban Americans — arguably empowered by their Cold-War-spawned exceptional treatment — had become an influential voting bloc in American electoral politics. And both political parties tried to win favor through policy, legislation, and sourcing for counsel.
The US trade embargo and Cuba’s post-Soviet economic crisis contributed to some 35,000 balseros — or rafters — fleeing Cuba for the Land of Freedom, safety be damned.
So, what does the Land of Freedom choose to do with the thousands-strong race for the American border?
Set an agreement in 1994 to admit at least 20,000 Cuban migrants a year; get the Cuban government aligned to discourage unsafe departures; and continue to send intercepted migrants to holding areas like Guantanamo Bay, Cuba.
American freedom not only has its limits but the country also engaged Cuba to effectively become a US Border Patrol subcontractor …
About eight months later, President Clinton’s administration signed another accord, which codified the return of Cuban immigrants to their homeland if they were picked up by US authorities before reaching American shores.
Most Cubans held at Guantánamo in 1994 and 1995 were subsequently allowed into the United States through humanitarian parole.
Cubans who reached US soil were generally allowed to remain and could later apply for permanent residency, as provided by the 1966 Cuban Adjustment Act.
These accords became the US “Wet Foot, Dry Foot” policy.
But doesn’t the policy strike you as weird?
That’s the nicest word I can use.
We’re talking about an agreement between the “Land of Freedom” and the “Land of Tyranny” to put more controls on the number of Cubans seeking freedom.
At the same time, the policy created an incentive for Cubans to risk dangerous journeys to America. Make it to American shores and you could stay. Get intercepted at sea, and you could find yourself back in Cuba.
No wonder many Cuban Americans were pissed. Or confused. The warning signs of Cuban nationals’ waning exceptional status were staring them in the face.
Movement 3: America Changes — And Time’s Up
History shows that Cuban exceptionalism began to fall apart years ago.
And after the contradictory policies of the 1990s, President Obama ended the “wet foot, dry foot” policy in 2017.
The move eliminated a major piece of Cuban exceptionalism for future unauthorized arrivals, bringing their treatment closer to that of other immigrant groups — save for the Cuban Adjustment Act, which remains in place.
And as if there weren’t enough irony, Jeh Johnson, Obama’s Homeland Security Secretary, said repealing “Wet Foot, Dry Foot” is part of the administration’s plan to normalize relations with Cuba.
Johnson even welcomed Congress repealing the Cuban Adjustment Act, but that never happened.
Much of the legal work had already been done over the years to make Cuban migrants removable like any other immigrant in America.
And Trump didn’t need to repeal the Cuban Adjustment Act to enable the kind of harm we’ve seen.
According to Human Rights Watch, the administration deported more than 4,300 Cubans to Mexico between January 2025 and March 2026. The organization documented failures to provide opportunities to contest removal to Mexico, along with cases of longtime US residents separated from their families and stranded without money, identification, housing, or a clear path to legal status.
Epilogue
I initially told myself that summing up the history of Cuban immigration to the US in a sentence like “From Freedom Flights to Miami to chartered flights to Central Africa” is outrageous.
But there are enough breadcrumbs that point to Cuban migrants’ exceptionalism being a convenient American propaganda play to hit Communism over the head.
A rare immigration privilege survived long enough to be mistaken for an enduring American promise.
But one can’t ignore the fine print now …
song currently stuck in my head: “three (vol. I)” – ivo perelman & matthew shipp
