Fidel Castro’s story is one of those rare tales in history that feels almost too dramatic to be real. Picture it: a young, fiery lawyer with a sharp mind and an even sharper tongue, standing against a government so corrupt and brutal that even its allies couldn’t deny it. Fulgencio Batista’s Cuba was a playground for the rich and a prison for the poor. American businesses thrived while Cuban farmers scraped by. Organized crime ran the show, and dissent? That was met with bloodshed.
And then came Fidel. Charismatic, relentless, and burning with a revolutionary fervor that electrified the oppressed. With a small band of rebels, including the enigmatic Che Guevara, he retreated to the mountains and launched a guerrilla war that captured the imagination of a nation. When Batista finally fled in 1959, it felt like justice had arrived. For the people of Cuba, Castro wasn’t just a man, he was a symbol of hope.
But revolutions, no matter how noble, rarely play out the way they’re imagined. Castro didn’t just overthrow a dictator; he tore down the old order entirely. Land was redistributed, businesses were nationalized, and Cuba became a socialist experiment just 90 miles from the United States. Education and healthcare? They flourished. Cuba’s literacy rates soared, and its medical system became the envy of developing nations. For a while, it seemed like the revolution might actually deliver on its promises.

Then the cracks began to show. The United States wasn’t going to let this small island become a beacon for anti-capitalism without a fight. The embargo hit hard, cutting Cuba off from vital trade and plunging its economy into chaos. But even as Washington squeezed, it became clear that not all of Cuba’s problems could be blamed on the embargo. Castro’s government controlled every aspect of life, and with that control came repression. Free speech? Gone. Political opposition? Silenced. Thousands of Cubans risked everything to flee, clinging to the hope of a better life across the sea.
Still, Castro’s supporters had their defense ready. “It’s the embargo,” they said. “How can you expect a country to thrive when it’s strangled by the world’s largest superpower?” And there’s some truth to that. The embargo did, and still does cripple Cuba in countless ways. But is that the whole story?
Even with the embargo, Castro’s centralized economic planning was riddled with flaws. Farmers had little incentive to produce, industries stagnated, and innovation was stifled. People queued for hours just to buy bread, and the island’s infrastructure crumbled. Meanwhile, the government’s grip tightened. The internet remained a luxury, accessible to few. Criticizing the regime? A dangerous gamble.
So where does that leave Fidel Castro? It’s tempting to cast him as either a hero or a villain, but the truth is far messier. He fought against a cruel regime, risking his life to bring justice to the oppressed. He stood up to U.S. imperialism with a defiance that inspired millions. But the country he built, a country he ruled for decades, never became the paradise he promised. Instead, it became a place where people traded one kind of oppression for another.

Maybe the real question isn’t whether Fidel Castro was a good man. Maybe the question is whether the revolution he led was ever capable of delivering the freedom and prosperity he dreamed of or if it was doomed by the very methods he used to achieve it.
You're giving way too much legitimacy to the narratives of the people who fled the country. Many of them came from wealthy land-owning families that were dispossessed during the revolution. Anytime you interact with anyone who is a refugee from a country that had a socialist revolution you will hear their stories of having their land taken, their "servants" set free, or their livestock taken to feed soldiers of the revolution. Their complaints are almost universally superficial and of the nature of property relations. You will have a hard time finding Cubans who fled for actual ideological reasons.
However, even when they claim ideological differences, they can't point to any actual policy where they differ. Look at the South Vietnamese or Kuomintang who fled China, they largely will claim they supported democratic freedom but what freedom existed in Kuomintang-ruled Taiwan or in South Vietnam? In actuality, there was almost none, these governments experienced more repression than any of the communist governments around the world would or ever have engendered.