In the twilight of the Castro era, change brings as much skepticism as hope

Walk along La Rampa, the main drag in what used to be Havana's version of a sleek 1950s American suburb, and every other bombed-out house seems to be sprouting a sign in its weed-filled garden, a table loaded down with secondhand Barcelona Football Club T-shirts. One woman sits by a rack of pirated DVDs, while her neighbor advertises DIGITAL PHOTOGRAPHS (FOR VISA OR PASSPORT). Someone has a sign up promising to repair your Rolex or Seiko watch, and a little handwritten notice in front of a crumbling terrace shows prices for coffee and orange juice (nothing else). Just a block or so off the busy street, a piece of paper announces, in English, ROOM FOR RENT. APRIL 18 AND 19. That was months ago.

You might be walking through a homemade rough draft of free enterprise that's being updated and revised daily. Nothing is hidden, but there's very little in the way of advertising, presentation or even fresh goods. A '52 Buick rattles past with a FOR SALE sign in its back window. It's long been legal to sell these old clunkers (many of which can fetch $25,000), but what's new as of 2011 is that Cubans can now sell late-model Kias, for $35,000--an impressive sum in a country where a high-ranking official earns $30 a month.

Three years after President Raúl Castro opened new doors to buying and selling, more than 300,000 Cubans are now their own bosses, trying to learn capitalism on the run, often with the help of supplies or remittances from loved ones abroad.

Just a few blocks up La Rampa, far from the old hotels associated with Frank Sinatra and Meyer Lansky, you come to a dark, state-run, Soviet-era department store. Carefully laid out in its windows are exactly four tubes of chewing gum, three bags of potato chips and one can of Vita Nuova pasta sauce. Inside, a single flimsy piece of Hello Kitty underwear sits in a dusty display case.

In a show of revolutionary spirit, anticipating the country's annual celebration of the fall of Fulgencio Batista's regime in 1959, someone has put up some letters on the store window, spelling out WE SALUTE THE 54TH ANNIVERSARY OF THE TRIUMPH OF THE REVOLUTION. But somehow the final R has gone missing, so the sign celebrates only the triumph of EVOLUTION.

Cubans "are not minimalists when it comes to paradox," as Cuban exile and Yale professor of history Carlos Eire has written. "We like our paradoxes rich and complex. The more labyrinthine, the better." The latest chapter in this long-running tragicomedy finds the government trying to maintain the state-run economy--and strict political control--even as it encourages its people to practice self-employment.

Thus it's possible now to sell new cars; it's just very difficult--you need a permit and a lifetime's official income--to buy them. It's finally possible for dissidents to leave the island, but no one knows how they'll be treated on their return. When an exiled Cuban now in Canada returns for a visit, all his relatives can meet and greet him--except for the one who serves in the army, who stands to lose his job if he talks to a "foreigner."

Cubans today are free--at last--to enjoy their own version of Craigslist, to take holidays in fancy local tourist hotels, to savor seafood-and-papaya lasagna with citrus compote, washed down by a $200 bottle of wine, in one of the country's more than 1,700 paladares, or privately run restaurants. They're free to speak out against just about everything--except the two brothers at the top.

Yet as what was long underground is now aboveboard, and as capitalist all-against-all has become official communist policy, no one seems quite sure whether the island is turning right or left. Next to the signs saying EVERYTHING FOR THE REVOLUTION, there's an Adidas store. "Nobody knows where we're going," says a trained economist whose specialty was market research, "and people don't know what they want. We're sailing in the dark."

"If you're talking about Cuba today, you have to say that we combine the worst aspects of socialism with the worst aspects of capitalism." His eyes flash with sardonic delight. "The worst of socialism in terms of oppression and denial of basic human rights. And the worst of capitalism in terms of exploitation and inequality!" The result is a limbo in which everyone seems to be robbing Pedro to pay Pablo.

Cuba was a riddle of exuberant dilapidation and gleeful disenchantment that was impossible to solve.

Over the course of my stays in the late 1980s and early '90s, I witnessed the country enter its notorious "special period" after the collapse of its Soviet sponsors in 1991; I visited friends in prison who said they were living better there--guaranteed food and comfort--than on the outside, and much of the time the only foreigners I saw were North Koreans.

"We've found solutions for three big problems: free health care, free education and, lately, free enterprise. Now we just have to find breakfast, lunch and dinner."

The gorgeous Cuban section in the Museum of Fine Arts is a state-of-the-art showpiece that would not look out of place in Dallas or Zurich. But toilet paper is rationed there. And if you want to wash your hands, you have to wait for an old woman to appear, pour some drops of mineral water in your palm and then squeeze out some soap from a hotel-room minibottle before extending her own palm for a tip.

Huge avocados go for 20¢, half the price they fetch in the capital. "For some people," says a man with little patience for the revolution, "Cuba is close to paradise. They say, 'Sure, this isn't heaven. But you know what? I don't have to work. I don't pay rent. Rum is cheap. I don't need a heater. I'm living in a beautiful tropical island. Who needs freedom?'"

The country's celebrated health care has won admirers throughout Latin America and the Caribbean even, it's said, among right-leaning governments.By now the revolution has exported doctors to more than 75 countries.

Yet typical of the paradoxes that haunt the island is the fact that the very excellence of its medical facilities has led to unintended consequences: Cuba's population is aging and shrinking so fast that one man in his 50s predicts he'll soon be living in a "wheelchair paradise."

By 2025, according to the National Statistics Office, Cuba will have the oldest population in Latin America or the Caribbean; 1 in 4 of its citizens will be over the age of 60, and the universities will have lost more than 30% of their students.

One of Fidel's proudest claims not so long ago was that his country, unlike its capitalist neighbors, had no beggars or people living on the streets. Nowadays, senior citizens in Havana may technically have homes to return to, but they look and act like homeless people, barely able to survive on pensions of $6 a month.

You still see signs here and there proclaiming SOCIALISM: TODAY, TOMORROW, ALWAYS, but in many places the old cry of "Socialism or death" seems to have been replaced by "The fatherland or death."

Those who recall the brutality and corruption of life before the revolution tend to be more forbearing toward the chaos now, but 5 Cubans out of 6 have never known anything but the shortages and convulsions of Castroism.

"In the 1990s, when we suffered from a lack of things," says a man who in recent years joined an evangelical church, "it was a real material crisis. But now it's deeper. We have a spiritual crisis. People have lost hope."

The deeper problem, especially for the young, is that there's every incentive not to get an education or a good, official job. In a country where a surgeon has to bicycle to work while a man selling fake cigars can dine, quite literally, on caviar, the government has done a fine job of educating its citizens and a terrible job of putting that education to use. "I tell my students, 'I know you can make more money now by driving a taxi than by being a good architect,'"

As it looks toward the future, Cuba could take heart, on paper, from China and Vietnam, both of which have retained a political grip on their people while giving them incentives to make money.

"When it comes to culture and core values, we have more in common with the economy of the U.S."

For 14 years, Cuba's shattered economy has been propped up by Venezuela, which sends roughly 110,000 barrels of oil a day to the island in exchange for Cuban medical personnel and teachers.

Raúl Castro, now 82, has always been seen as less prideful and doctrinaire, if less charismatic, than his brother, who's five years older; he rules in prose, not in Fidel's combative poetry. And when Castro announced in February that he would not seek re-election in 2018, all eyes turned to his presumptive successor, Miguel Díaz-Canel, a 53-year-old technocrat and former military man who served as a party official in areas where there were abundant opportunities for foreign investment. Even as Castro spoke of term limits and referendums in the future, Cubans began to imagine, at last, a pragmatic leader born after the revolution--and one not named Castro.

For now, though, there's no one to give Cuba a stirring sense of itself, a winning story, as is sometimes said of Obama's America. The fact that the revolution keeps showcasing portraits of Che Guevara and Camilo Cienfuegos, dead for 46 and 54 years, respectively, underlines the absence of fresh heroes.

"As I see it, there are basically three options for the future," says one Habanero who's never left the country, "and all of them are horrible. I call them the North Korean, the Afghan and the Russian versions.

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