Published on: Sat, 21 Mar 2026 06:00:01 GMT
Original Story: Opinion: As Trump eyes Cuba, my trips there a decade ago remind me how different things were – CNBC

Cuba Libre? More Like Cuba Maybe Later.

So, CNBC’s got some op-ed about Trump eyeing Cuba again. *Yawn*. Look, I get it. Exotic locales, forbidden fruit… it’s like that one time you tried to sneak into a rated-R movie in 8th grade. But let’s be real, Trump’s “interest” in Cuba probably stems from a fleeting thought he had while watching a rerun of Miami Vice. Remember Miami Vice? Shoulder pads, pastels, and enough cocaine to fuel a small rocket. Good times. Anyway, let’s unpack this Havana-flavored hot mess, shall we?

Trump’s Two-Step with Cuba: A History of… Steps?

Oh, where to even begin? Trump’s relationship with Cuba is less a coherent policy and more a toddler banging on a piano – loud, unpredictable, and ultimately, not very harmonious. Remember when Obama, in a move that actually made sense, started normalizing relations with Cuba? I know, I know, remembering Obama-era policies feels like ancient history these days, akin to remembering when you could afford a house without selling a kidney. But it happened. Embassies opened, travel restrictions eased… for a hot minute, it looked like we might actually move past the Cold War.

Then Trump came along. In 2017, he promptly reversed a bunch of Obama’s progress. “Human rights,” he declared, were the sticking point. “We will not lift sanctions on the Cuban regime until it meets our demands.” Strong words, right? But words are cheap, especially coming from someone who probably thinks the Cuban Missile Crisis involved a particularly spicy salsa.

But Why the Sudden Interest Now?

That’s the million-dollar question, isn’t it? Is it genuine concern for the Cuban people? Doubtful. Is it a calculated move to win over the coveted “anti-communist” vote in Florida? Ding, ding, ding! We have a winner! It’s always about the votes, folks. Always. Let’s not pretend this is some grand ideological crusade. This is politics 101, with a side of mojitos.

And what about the potential economic benefits? Sure, American businesses are salivating at the prospect of getting a piece of the Cuban pie. But is that pie worth the potential diplomatic headache? Is it worth alienating allies who’ve already established a foothold in the Cuban market? These are questions someone with a long-term strategic vision might ask. But, you know… details.

The Reality on the Ground: A Decade Ago vs. Now

CNBC’s opinion piece talks about how things were a decade ago. Fair enough. A decade ago, I was still clinging to the naive belief that hard work and a good education guaranteed success. Ah, youth. Anyway, a decade ago, Cuba was still very much a time capsule. Classic cars, crumbling buildings, and a palpable sense of… well, let’s call it “constrained optimism.” The people were warm, the music was infectious, and the rum was plentiful. But the economic realities were harsh. Access to information was limited. Opportunities were scarce.

Has much changed? Probably not enough. Sure, there’s been some limited economic reform. More people are starting small businesses. Internet access is (slightly) less of a luxury. But the fundamental problems remain. The government is still firmly in control. Political dissent is still suppressed. And the economy is still… well, let’s just say it’s not exactly booming. So Trump waltzing in with promises of economic salvation? It’s a bit like offering a band-aid to someone with a broken leg.

Remember the Tariff Tracker? Oh, the Irony.

Speaking of economies, let’s not forget the Tariff Tracker, shall we? Remember when Trump was slapping tariffs on everything that moved, supposedly to “protect American jobs”? The irony of him now potentially opening up trade with Cuba, while simultaneously threatening to slap tariffs on other countries, is thicker than a Cuban cigar. It’s like he’s just throwing darts at a board labeled “Global Economics” and hoping something sticks. Spoiler alert: it usually doesn’t.

The Loyalty Test: Who’s Really Being Tested?

Honestly, this whole Cuba thing feels like another loyalty test. Not for Cuba, but for the Republican base. How much will they swallow? How much hypocrisy can they stomach? Because let’s be honest, Trump’s foreign policy is less about principles and more about… well, whatever pops into his head on a given Tuesday morning. And if that Tuesday morning happens to involve a craving for a good mojito and a fleeting thought about winning Florida, then… *poof*, Cuba policy gets a makeover.

And what about the Cuban-American community, particularly in Florida? They’ve historically been staunchly anti-Castro (for very good reasons, let’s be clear). Will they see this as a betrayal? Or will they see it as a shrewd political move? My guess? A bit of both. They’re not stupid. They know what game is being played. But they also know that politics is a messy business. And sometimes, you have to hold your nose and vote for the lesser of two evils. Or, in this case, the lesser of two potential dictators.

Snarky Takeaway

So, where does this leave us? Probably right back where we started. Trump will make some grand pronouncements about Cuba. He’ll dangle the carrot of economic opportunity. He’ll probably even tweet something vaguely threatening about “regime change.” And then… nothing much will happen. Because that’s the Trump playbook, isn’t it? Lots of talk, very little action. And in the meantime, Cuba will continue to be Cuba – a beautiful, complicated, frustrating, and ultimately, resilient island nation. And we’ll all be left scratching our heads, wondering what the hell just happened. Pass the rum.