Here we go again. It is the same old song and dance, just with a louder singer. **Donald Trump is back to squeezing Cuba**, and if you have been alive for more than ten minutes, you know how this goes. The United States decides it hates the island next door, and the machine of **US foreign policy** grinds into gear. The big man in the White House signs some papers. He talks tough. He says the bad guys are finished. And what happens? Absolutely nothing. The bad guys stay in charge, and the regular people suffer. It is the definition of insanity, but in Washington, they call it strategy.

Let’s look at the facts regarding the **history of the US embargo on Cuba**. This has been going on for almost seventy years. Seventy years! That is longer than most of you have been alive. President after President has tried to bring down the Communist government in Cuba. Eisenhower, Kennedy, Nixon, Clinton, Bush, Obama—they all had a turn. They all failed. The Castros outlived almost all of their enemies. It is actually kind of funny if you stop thinking about how sad it is. The most powerful country in the history of the world cannot figure out how to handle a tiny island that is basically running on classic cars and spite.

Now, the news says this time "feels different." Does it? Because to me, it looks like the same old garbage. Trump thinks he is the special one. He thinks he has the magic touch that will finally break the system. It is pure ego. He wants the trophy. He wants to be the guy who says, "I did it. I won." But he doesn't care about the details. He just wants the applause. He wants the **Florida swing state votes**. That is what this is really about. It is always about votes. If there were a bunch of voters in a swing state who loved Cuba, Trump would be building a hotel in Havana tomorrow. That is how these people work. They have no spine. They just follow the noise.

On the other side, you have the Cuban government. Let’s not pretend they are the good guys. They are not. They are a dusty, broken relic. Communism there is a joke. It is a system that keeps the bosses fat and everyone else hungry. They cling to power like a drowning man holding onto a rock. They blame everything on the United States. If it rains too much, they blame the embargo. If the power goes out, they blame the Yanks. Trump squeezing them just gives them a better excuse. It helps them. It gives them a reason to tell their people, "See? The Americans hate us. We must stay strong." It is a perfect circle of stupidity. Trump gets to look tough for his fans, and the Cuban leaders get a scapegoat for their failures. Everyone wins, except the people who actually live there.

Think about the actual strategy here. The idea is to squeeze the country so hard that it breaks. They want to make life so miserable for the average Cuban that they rise up and overthrow the government. That is the plan. Think about how cruel that is. The plan relies on starving regular people. It relies on making sure a mom cannot get medicine for her kid. It relies on making sure there is no gas for the bus. The suits in Washington sit in air-conditioned rooms and decide that Jose in Havana needs to suffer more so that democracy can win. It is gross. It is immoral. And worst of all, it doesn't even work.

We have tried starving them for decades. It hasn't worked yet. Why would it work now? Because Trump tweets in all caps? Please. The people in charge in Cuba have guns and tanks. Hungry people with rocks don't usually win against tanks. But nobody in our government cares about that reality. They just care about the soundbite. They care about looking strong on TV.

This is why I hate politics. It is all theater. The Right screams about freedom while crushing an economy. The Left cries about human rights but ignores the reality of the dictatorship because they like the aesthetic of the revolution. Both sides are playing a game. They are moving pieces on a board. They don't see the humans. They just see points to be scored.

So, Trump is squeezing Cuba. Again. Maybe the economy there will finally collapse. Maybe it won't. But I can promise you one thing. The politicians who made the mess will sleep just fine in their soft beds. They will eat their steak dinners. They won't miss a meal. Meanwhile, ninety miles away, people are wondering where their next meal is coming from. And they are stuck between a stubborn, useless government at home and a bully neighbor to the north. It is a hopeless situation. But hey, at least it makes for good headlines during election season, right? That is all that matters to these grifters. Welcome to the show.

### References & Fact-Check * **Original Report:** [Trump Squeezes Cuba (The New York Times)](https://www.nytimes.com/2026/02/24/world/cuba-trump-oil-tourism-russia-economy.html) – The primary source detailing new economic pressures on Cuba's oil and tourism sectors. * **Historical Context:** The piece references the nearly 70-year timeline of US-Cuba relations, spanning administrations from Eisenhower to the present day.