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My first visit to Cuba, in 1990, came at what then seemed like the darkest hour of Fidel Castro’s rule.

The reformist Soviet president, Mikhail Gorbachev, had recently traveled to Havana to inform Castro that the decades-long period of Moscow helping to keep the Cuban economy afloat through generous subsidies and barter trade arrangements was ending. Gorbachev had his hands full with a crisis-ridden economy back home and could no longer afford to play the generous patron to a distant ideological ally.

My first visit to Cuba, in 1990, came at what then seemed like the darkest hour of Fidel Castro’s rule.

The reformist Soviet president, Mikhail Gorbachev, had recently traveled to Havana to inform Castro that the decades-long period of Moscow helping to keep the Cuban economy afloat through generous subsidies and barter trade arrangements was ending. Gorbachev had his hands full with a crisis-ridden economy back home and could no longer afford to play the generous patron to a distant ideological ally.

The effects of Moscow’s sharp change of course rippled through every facet of life on the island. Big industrial projects were mothballed, including a half-built nuclear power plant. As Cubans were forced to tighten their belts, imported foodstuffs disappeared from shelves, and gasoline—long supplied by Russia at a steep discount—became scarce.

Over the next few years, returning to Cuba as often as I could, I observed as what had begun as a kind of death watch for the Castro era turned into something else entirely: The Cuban state and the Cuban people both made a series of grueling adjustments during this time, known as the “special period,” and before long, talk of a collapse morphed into a make-do economy centered on survival.

That experience has made it hard for me to watch Washington revive the fantasy that Cuba is just one shock away from collapse and that U.S. pressure can deliver the decisive blow.

Outside of south Florida, which is home to the island’s largest diaspora,........

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