COMMENTARY The fact that Cuban leader Raúl Castro likely deserves his U.S. indictment for killing exiles in 1996 is exactly why President Trump will likely have big trouble removing him in 2026.
Barack Obama did almost everything right on his historic presidential trip to Havana a decade ago.
Except one, glaring thing: going to a baseball game with then Cuban President Raúl Castro.
Obama’s visit in March 2016 focused, appropriately, on the reason he’d normalized relations with Cuba two years earlier: not to make nice with the island’s repressive and disastrous communist regime, but to undermine the decades-old dictatorship by getting a U.S. foot in the door in order to bolster what non-state, civil-society, quasi-independent elements existed there.
He met with dissidents, exalted Cuba’s fledgling private sector — he even ate at paladares, private Cuban restaurants — and he challenged Castro, in a speech at Havana’s Gran Teatro, to stop being afraid of his own people.
But then Obama compromised those firm optics by cozying up with Castro at that ballgame.
READ MORE: Is reasoning in Havana more effective than railing from Miami? Sí
Why did that matter? Why should Obama have kept more distance?
We were reminded of the reason this week, when the Trump administration indicted Raúl Castro for allegedly ordering the Feb. 24, 1996, shoot-down of two small, unarmed airplanes off Cuba. The attack killed — murdered, as the indictment claims — the planes’ four Cuban exile occupants.
Castro, then defense minister, insisted the Cessnas, operated by the exile group Brothers to the Rescue to aid Cuban rafters in the Florida Straits, were a security threat. But he and the regime knew the only danger they posed was dropping anti-communist leaflets onto Havana’s Malecón. It was hardly another Bay of Pigs invasion.
The truth is, for 30 years Castro has likely deserved the U.S. indictment that came his way on Wednesday.
That’s why Obama should have been a tad more aloof in 2016.
It’s also why, in 2026, President Donald Trump isn’t likely to get rid of the 94-year-old Castro, or the dictatorship Castro still in reality leads, as soon or as easily as he believes.
Any man, and any regime, that can carry out what Castro and his air force did in 1996 is not the easy target that Venezuela’s U.S.-indicted dictator was.
That’s because any man, and any regime, that can carry out what Castro and his air force Migs did in 1996 is not the easy target that Venezuela’s U.S.-indicted dictator, Nicolás Maduro, turned out to be when he was captured on Jan. 3 by the U.S. special forces Trump sent into Caracas.
Maduro, for all the terror he and his security goons inflicted on Venezuelans, was in the end a clown.
Iron apparatus
Raúl Castro, on the other hand, is KGB — a serious, Stalin-style autocrat who, despite his age, still commands an iron apparatus that is not going to roll over for Trump the way Venezuela’s did.
This week I spoke with acclaimed Cuban exile historian and Princeton University professor Ada Ferrer about her new memoir, Keeper of My Kin — but in our conversation I couldn’t help think back to her Pulitzer Prize-winning 2021 book, Cuba: An American History, and its chapter on the 1962 Cuban missile crisis.
In it, Ferrer follows Castro’s brother, the late Cuban dictator Fidel Castro — who a year earlier had fought off the exiles’ Washington-sponsored Bay of Pigs assault — as he rails at his Soviet patrons to nuclear-annihilate the U.S. at the first hint of yanqui invasion of his kingdom.
In Ferrer’s narrative, then Soviet leader Nikita Khrushchev seems to consider Fidel a madman. But Fidel welded that Cuban communist zealotry — akin to the Iranian Islamist fanaticism that’s also stymying Trump right now — into the mindset of the hierarchy Raúl still lords over.
Which is why Trump has been screaming at aides in the White House to explain why Cuba’s regime, despite his de facto oil blockade and all the other economic pressure he’s heaping on the island, hasn’t yet agreed to adopt democratic capitalism or just leave power altogether.
It’s because the Cubans know that Trump knows that any U.S. military incursion there, be it to merely arrest Raúl or outright overthrow the regime, will likely be a hundred times messier for Trump than Jan. 3 was.
And, as Ferrer pointed out in our conversation, Trump hasn’t exactly discouraged the regime’s volatile siege mentality with his own erratic remarks, like: “I’ll have the honor of taking Cuba … and I can do anything I want with it.”
To that, a worse authoritarian bully like Raúl Castro would reply:
Before you try to repeat Jan. 3, 2026, remember Feb. 24, 1996.
