IN CUBA, THE years immediately following the collapse of the Soviet Union are known as "the special period."
It is a euphemism of the highest order. The withdrawal of aglobal superpower, which had been propping up the Cuban economy with subsidies estimated at $6 billion a year, brought almost unimaginable misery to the tiny nation. Gross domestic product plummeted by more than a third from 1989 to 1993. Daily power blackouts became common. Farms and factories sat idle. So hungry were the Cuban people that cats disappeared from the island--"and doves and pigeons," says Leo, my 30-year-old guide in Havana this summer. He's not the only one to mention the cats.
Leo grew up in a Communist family, so there was no questioning the political system in their household. The state offered meager rations of food--drastically reduced from the quantities in the '70s and '80s, according to Oxfam--but at least it was something. His mother was employed by the Cuban military, which provided lunch to its workers. She would save it, bringing it home, so her kindergarten-age son could have at least one meal a day.
The special years took a toll. The average Cuban lost 12 pounds. Some estimates put the figure at 20.
Which, after all, was what America's policy toward Cuba had been aimed at all along. For decades, U.S. politicians have believed empty bellies are the best way to bring Cubans around to the virtues of a market economy and electoral democracy. "If they are hungry," President Dwight Eisenhower allegedly said, "they will throw Castro out." In 1962, President John F. Kennedy called for a total embargo on the country. In 1994, the conservative Heritage Foundation argued for maintaining the ban: "As the economy's collapse has accelerated, popular discontent has increased to levels that threaten the survival of the regime."
But the disaster of the special period had an unexpectedly trivial effect on the Cuban government's legitimacy. One-party rule continued. Fidel Castro remained.
The material conditions of the average Cuban have improved since that dark time, partly because of the country's close ties to oil-rich Venezuela, and partly because of moves by the Castros--reluctant at first, later with more confidence--to let a non-governmental sector begin to bloom.
Today, Leo works with an American tour company as a self-employed "travel curator," earning many times more than he did during his mandatory year of military service. At the end of our three-day stay this June, each member of my group chipped in $20 as a tip for him. Any one of those contributions was, by itself, nearly as much as a typical public-sector worker in the country earns in a month.
Their new wealth has affected Leo's family in ways the desperate poverty of the special years did not. "When we had nothing," he says of his mom, "she was a blind Communist. Only now that things are better, and you open the fridge and it's so full of food, so much food that you don't have to worry anymore," has she come around to the merits of capitalism.
But the progress on the island may be endangered. This summer, President Donald Trump moved to roll back a three-year-old rapprochement between Cuba and the United States. Hundreds of thousands of Americans have visited the country during the brief period of openness, pouring hundreds of millions of dollars into Cuba's economy. That infusion now seems poised to dry up as quickly as it started.
The experience on the ground is one of whiplash. Just 15 months before my trip, President Barack Obama traveled to Havana and, in a speech deliberately aimed at the Cuban people, said he had "come to bury the last remnant of the Cold War in the Americas." Trump's reversal is causing trepidation. And everywhere I went, I heard the same thing: If the U.S. isn't careful, the whiplash may become a backlash in which "hardliners in the government are empowered" and citizens "close ranks around the revolution."
A SELF-EMPLOYED TAXI driver picks me up in a '50s Chevy from the private home where I'm staying. He whisks me off to a paladar, or individually owned restaurant, which a friend chose after consulting AlaMesa, the Yelp-like Cuban smartphone app that even without an internet connection directs people to highly rated establishments. (Users update the app whenever they manage to get connected to the country's few sporadically available Wi-Fi nodes.) Along the way, we pass a hip storefront selling T-shirts and posters screen-printed on site with fun slogans. Los Cubanos no le tenemos miedo al calentamiento global. Porqueya estamosen llamas, reads one of them: "Cubans are not afraid of global warming. We are already in flames."
This sequence of events would have been inconceivable for a tourist in Cuba a few decades ago. Now it's the norm for urban travelers. The Communist Party may have no intention of relinquishing political control in the country. But it has, if only out of necessity, gradually slackened its grip on the economy.
After Fidel Castro and his socialist revolution rolled into Havana in January 1959, America reacted with horror: Suddenly, it seemed the Soviets might have a foothold just 90 miles off the coast of Florida.
At the same time, an exodus of supporters of the ousted Cuban regime--many of whom had left behind valuable property when they fled--made their way to the United States and began agitating, forcefully, for America to get involved. Fortunately for them, Fidel offered Eisenhower plenty of excuses to acquiesce, from nationalizing U.S. assets on the island to summarily executing 200 political opponents via firing squad. Something, the White House agreed, needed to be done.
Initially, the goal was to depose the Cuban leader by force. But after the Cuban Revolutionary...