Havana hustle: Cuba's new socialist man learns to wheel and deal.

I MET PABLO IN December at a rooftop bar offering cheap cocktails, lives salsa, and an expansive view of Havana Harbor. Pablo--his name and the names of other Cubans in this story have been changed to protect them from punishment--was 28 years old, a budding capitalist with a strong code of ethics. He laid fiery scorn on the city's jinteteros, male "jockeys" who hustle tourists for tips and commissions. He mocked their aggressive approach--"Hey, you need cigars? Una chica?"--and insisted they were ruining Cuba. Sure, Pablo himself found restaurants for tourists when they asked, and at our request he led two friends and me to a dark, lusty nightclub (appropriately named Las Vegas), where he earned $15 off our $56 tab. But for the most part, Pablo supported his sick mother and younger sister through more legitimate means. Instead of pushing overpriced restaurants, tobacco, women, or drugs, he sold his own paintings, Crayola-bright Cubascapes that tourists bought for $20 or more.

Pablo reveled in the fact that he taught himself to paint, then learned English to increase sales. "I'm different," he told me. "I always earn money without hurting anyone."

Five months later, on a sweaty spring night, Pablo repeats this claim. And with me, he's always lived up to it, going so far as to return commissions culled from our shared meals and drinks. But a lot has changed since December, and it's not at all clear that Pablo and others like him will manage to hold onto their scruples. Cuba today is wracked with silent fear. In the wake of a massive spring crackdown on independent thought and action--Castro has tossed nearly 80 dissidents in jail, executed three boat hijackers, shuttered home-based businesses, and closed at least one popular discotheque--few feel secure. Jineteros nowwhisper or quickly demand dollars. Educated Cubans hide American books at the first sign of a visitor. Black marketeers sweat the sales they need to survive. It's as if Havana were the setting of a metropolitan hide and seek, with all the citizens holding their breath to keep from being found by Fidel.

Amid such suffocation, nearly everyone must consider an immediate shift in course--especially in Cuba, where an estimated half of all retail transactions take place in the black market. But to understand how today's oppressive atmosphere fits into not just Cuba's present but its past and future, there is perhaps no better place to look than the world of jineterismo Because they work in the streets under the nose of the regime, jineteros have become Cuba's ultimate evolvers, hurricane-quick adapters who bob and weave whenever political muscle appears. Mostly in their teens and 205, they offer a vital glimpse into both what people are being forced to do today and what they'll likely pursue tomorrow.

Neither insight is encouraging. In more ways than one, Castro is turning would-be capitalists into criminals. At this point, not even Pablo is the man he used to be.

Black and Gray Markets

Pablo's relationship to jineterismo, Fidel, and capitalism includes fits and starts, triumphs, trials, and plenty of errors. But in each case, Castro made the first move.

The pattern started in At the time, Pablo was 18 and Cuba was dying. Without the Soviet Union's oil and its $4 billion in annual aid, the island could barely function. Blackouts darkened the Cuban night. Malnutrition returned to the countryside, and inflation skyrocketed. Cuba was doomed, Andres Oppenheimer declared in his 1993 book, Castro's Final Hour; it would soon disintegrate into chaos.

But stories of Castro's demise have always been greatly exaggerated. Suddenly, he let loose the reins. Self-employment in dozens of formerly black market occupations became legal. Such activity has been a part of Cuba's economy since Spanish rule, when officials earned low salaries and were expected to pad their incomes through corruption. Because the post-Soviet black market had swelled to politically threatening proportions, Castro decided to co-opt it.

He also gave his blessing to dollars. Once outlawed as the currency of imperialism, greenbacks suddenly became not just accepted but necessary. Without American cash, it was nearly impossible to obtain shampoo, appliances, decent shoes, and other items the state could no longer provide.

The economists who convinced the government to accept minimal reforms said they wanted to give markets an active role, "neither exclusive nor dominant." Castro, meanwhile, wanted only a tightly limited infusion of free enterprise. "We will have to improve and perfect socialism, make it efficient but not destroy it," he said in 1993. "The illusion that capitalism is going to solve our problems is an absurd and crazy chimera for which the masses will pay dearly."

This ambivalence created gnarled, often schizophrenic markets. While a significant part of the regime's survival strategy depended on opening the country to tourism, for example, restaurants and bed and breakfasts were not allowed to advertise or to hire anyone but immediate family. The former prohibition essentially created jineterismo: Without advertising, one-on-one marketing to the masses became the bestwayto drum up business.

Pablo--a trim feet, 9 inches, looking more like a shortstop than a businessman--still recalls the day he raised the issue with his family. He had just finished school, and rather than work for the state he wanted to try earning dollars on the streets. His family needed cash. He was the only man in the house. His mother was often bedridden with severe arthritis, his younger sister and her daughter were still in school, and Pablo, as a black man without political connections or an appropriate degree, would never be able to get a tourism job that offered legal access to dollars. Becoming a jinetero, he argued, was the only option.

At first his mother and sister rejected the idea. "They didn't want me to do it," Pablo tells me in his simple concrete house on the outskirts of Havana, where he still lives with his mother, sister, and niece. "They thought it was dangerous. They thought I'd be arrested?'

Eventually, though, his family relented. The cutbacks in food and services provided by the state were simply too much to bear. Besides, they figured, when the government has the cojones to ban Cubans from entering hotels and tourist restaurants, why treat the law as sacred?

Business was relatively good at first. The number of tourists visiting the island increased by 15 to 20 percent a year throughout the mid-'90s, and tourist-focused businesses took off. By the end of 1995, according to government statistics, Cuba had more than 208,000 licensed independent workers (called cuenta propistas) , 64,000 of them in Havana. As a result, young men like Pablo, who always made sure to tuck in his shirts and look clean, had little trouble satisfying the foreign, sunscreened hordes while earning at least twice the salary of a Cuban doctor (400 pesos, or about $16, a month). More impressively, they managed to do it without the widespread violence and crime usually associated with informal hustling in countries such as Jamaica. Pablo, it seems, wasn't the only one trying to "make money without hurting anyone."

Until 1996. That's when Castro rewrote the market's rules. Fearing the genie he'd unleashed, and with the economy improving, Fidel "rectified" the situation. A series of new laws demanded everything from the re-registration of the self-employed to income taxes that often topped actual income. Nearly every entrepreneur suffered. Within two years, the number of registered independent workers dropped by nearly half. According to Ted Henken, a Cuba specialist at the City University of New York (CUNY), by 2000 only 200 home-based restaurants (paladares) were registered and in business on the entire island, a decrease of more than 85 percent.

Pablo felt the impact more immediately than most. By the summer of 1997, he'd grown desperate. He couldn't find a state job that paid enough, and the open friendliness required for successful hustling attracted police attention. So Pablo asked his sister Susanna to work with tourists in Varadero, a beach community two hours outside Havana. Pablo knew this meant she would be tempted to sleep with men for money. He knew that jineteras were expected to have sex with their customers. He says that the idea made him nauseous, and that when Susanna agreed to go he hoped she'd be the exception. In any case, with a sick mother to care for and no other source of income, he and his family had no choice. "I was having such a hard time," Pablo says. "I figured maybe she'd be luckier because she's a woman."

Pablo's dubious suggestion was hardly unique. During the so-called Special Period of the '90s, a swift trade in sex tourism began to develop in Cuba, and many women chose to seek out foreign boyfriends instead of Cuban jobs. Unfortunately, Pablo's sister started at a dangerous time. In addition to the new laws, Pope John Paul II was scheduled to visit Cuba within a few months. Castro accordingly embarked on a moral crusade against prostitution. Two months and one boyfriend after she started, Susanna was arrested. The Italian man she'd befriended couldn't do her any good. The handful of dollars she'd earned were useless. Without a trial or a lawyer, she received the standard harsh sentence of the time: two years in prison.

When the Pope arrived in January, the streets along his route were as clean as the Vatican's.

Hustlers and Soft Sells

Susanna doesn't seem angry at Pablo today. She refuses to talk about what prison was like, but when we met she and Pablo were joking around about dinner, clothes--typical sibling banter. If there was a long-term scar from the experience, it didn't show.

For Pablo, though, Susanna's arrest became yet another turning point. If the regime's 1996 crackdown pushed Pablo's sister to the streets, her arrest threw him in the opposite direction. At first, Pablo simply wallowed in sadness and anger. "I cried for like a year," he says. "I went crazy knowing she was in prison because of me." But after several months, the pressure to provide mixed with the regret over his sister pushed him to adjust once more. This time, he focused on a long-term investment: education. By learning English and painting, he hoped to broaden his market.

He aimed to avoid the seedier side of serving tourists, and according to his mother, "He worked very hard." When Pablo showed me a series of notebooks full of English vocabulary lists and self-created grammar drills, I had to agree. Not that his English and painting were done for self-improvement--whenever I ask Pablo about his artistic influences, he laughs. "I paint whatever the tourists want," he says. Art, he argues, is only an economic tool, the key component of a survival strategy.

It was through painting, though, that Pablo began to realize the benefits of the soft sell. He began to see that if he could get tourists to like him, to feel comfortable, they were more likely to buy a painting from him. If he sold them something they liked, they might even refer their friends to him.

Talking to tourists, then, became an attempt to create an ongoing relationship. His methods were simple but were unusual in Havana. "I always carry $2 or $3 in my pocket so I can go into a bar and meet tourists," he told me in December. "If they see me and I'm sitting down and buying my own beer, they trust me."

"I'm different from the others," he added. "I don't sell tobacco on the streets. I don't bother tourists. I get them to trust me. They ask me for things and I help them."

What the tourists don't know is that Pablo's help earns him commissions. A mojito ordered at most bars will net Pablo a dollar. Dinner for four at a paladar will bring him a few greenbacks and some oil or rice or beans. Taxis, rented rooms in people's homes, cover charges at discos, women, men--everything in Cuba comes with a commission that usually amounts to between 10 percent and 25 percent.

Cubans still aren't sure what to make of such work. Some shrug it off as a necessary tactic. Others, especially the licensed business owners whom the jineteros serve, complain about their presence, if only because they resent the commissions. The regime would rather do without jineteros as well: In the May 4 English edition of Granma, Castro's state mouthpiece, one of the three executed hijackers was described as a criminal who "was given an official warning about harassing tourists 28 times."

Still, it's clear that hustlers don't benefit only themselves. Most of the 50 or so jineteros I've spoken to since November say they support at least two other people. They may just be telling me what they think I want to hear, but I've visited enough homes and interviewed enough extended family to confirm the substance of their claims. Pablo's neighborhood, for example, shows clear signs of a multiplier effect. All the houses, single-story three-room ranches, have been renovated in the past two years--thanks in part to tourism-related money. Neighbors with larger unofficial incomes, like the beer delivery-driver who sells poached cases on the side, have used better materials and brighter, fresher paint. But everyone in Pablo's barrio seems to have benefited from those who have contact with foreigners.

It's an ongoing process. When we walked out of his neighborhood, Pablo was stopped several times for help. One man, with a weathered face and torn jeans, requested a pair of shoes; another asked when Pablo was going to teach him English.

I've seen this communal approach to commerce throughout Cuba, especially among independent workers such as the repairman who silenced my noisy air conditioner with the help of two apprentices. It could be a pleasant aftertaste of Cuban socialism. Or perhaps it's an example of the solidarity that develops among citizens of a decaying authoritarian state. Regardless, I couldn't help but feel encouraged by the team effort. In these connections and webs of support, I saw future community-focused businesses: an English language school here, a construction company there.

But will it ever happen?

Sex, Drugs, and Rule of Law

The entrepreneurial and hustling scene in Cuba changes with the speed of a thunderstorm. Researchers like CUNY's Henken have shown that Cubans rarely cease engaging in commerce when the government acts, choosing instead to route around the problem with innovative adjustments. Some of these are relatively harmless. The commission system, for example, is a way to ensure payment for an illegal but often necessary task. Other shifts, however, do not bode well.

When I visited in December 2002, for example, sex and drugs were being sold more openly than during my previous visit, a year earlier. Prostitution in Cuba is nothing new, of course, but in the past such transactions were usually initiated without pimps. Not anymore. I discovered this first on the tourist Fifth Avenue of Obispo Street, when a short, thirtyish man offered me his teenage sister for $15 a night. Then I saw the hustlers on the Prado hawking the women who sat beside them. Finally there was the jinetero in the seemingly new Polo shirt--he looked about 18 years old--who brought me to a smoke-filled room on the second floor of a decayed colonial building in Old Havana. There, for only $10, I could gain access to loud music and 100 women who ogled me like I was pure gold when I peeked inside.

Drugs remain a far less developed market. Hustlers who rub their nose to signify sales of cocaine remain rare, and marijuana offers are not much more common. In fact, when I refused to buy a joint from one Tommy Hilfiger-clad hustler in central Havana, he badgered me for prices. "How much should I charge?" he asked. "What's a joint cost in the U.S.?"

Still, the emergence of even clueless drug dealers is hardly cause for celebration. When illegal, drugs tend to breed violence. As Dennis Hays, executive vice president at the Cuban American National Foundation, points out, "It's a very short step into crime--muggings, flimflam, rolling people, pickpocketing."

The present crackdown, Hays and others argue, will only accelerate the process. Already, says Henken, "A lot of people are going underground and are being forced into more pernicious activity because there's not much space to survive.

With characteristic Cuban pride, the jineteros disagree. They tend to see themselves as the country's future business leaders. They know they will outlive Fidel, and many--like Manuel, a 20-year-old law student who's aiming for a career in international commerce--are preparing for the imminent transition to capitalism. And don't worry about violence, a scraggly-bearded hustler on the Malecon told me in May. After all, he said, "Cubans are not terrorists." The only people who died in the spring spate of hijackings "were killed by el gobierno."

But even if crime remains under control, the government's restrictive approach to capitalism will likely inflict more subtle but still painful wounds. Scholars, though quick to point out that no scientific study has captured jineterismo's true impact, tend to be pessimistic about Cuba's informal markets. They argue that the most troubling portents are not physical but cultural.

"It's important to recognize that the problems communist countries have is a lack of rule of law," says economist Joseph Stiglitz, a former vice president at the World Bank and the author of Globalization and Its Discontents. "This is the inheritance of communism."

Cuba is no exception, and according to some, jineteros will only make future chaos more difficult to avoid. "The jineteros could not function without the theft that takes place from the enterprises that are owned directly or indirectly by the state," says Nelson Valdes, a Cuba-focused sociologist at Duke. "Thus, the jineteros are hardly a positive force for economic enterprise or labor discipline."

The short-term nature of tourism--combined with laws prohibiting capital investment and rhetoric that treats tourism as a temporary bandage that will soon be discarded--teaches jineteros to ignore the value of long-term economic relationships. "Every tourist that walks down the street is someone who you're hoping to use for an evening at most," Hays says. "It's a dog-eat-dog capitalism. It's not Junior Achievement in action."

CUNY's Henken, who has conducted more field research on jineterismo than just about anyone, takes a more balanced view. People like Pablo play a positive role, he says, by providing for their families and creating an alternative to the state-run system. But the benefits may be only temporary. Now more than ever, Henken says, Castro is turning "a reservoir of entrepreneurial talent" into "a swamp of corruption."

New Whims

Pablo's experience confirms Henken's claim. When we meet in May for a drink on Obispo Street, changes surround us. A nightclub around the corner, El Bohemio, has been closed. Police stand outside in larger numbers. Even the bar's usual hipster jazz band is gone. In their place stand five older Cubans who, according to the bartender, "played in the cemetery before coming here." It turns out we were lucky to have music at all: I later learn that most of the young, talented bands can no longer play in the bars, for reasons unknown.

I ask Pablo about a new hustling law I've heard about from other jineteros. Is it true that people caught talking to tourists five times have to spend a year in jail or pay up to 600 pesos, more than a month's salary? "Si," he says. "But it's not a new law. It's a new whim."

"What's it mean for you?" I ask. "Are you still painting?"

"Not like before," Pablo says. He goes on to explain how his brother kicked him out of the studio they were sharing because he couldn't pay his share of the necessary taxes. "I paint at home a little bit now, and it's better because it's just for me," he says.

We get up and start walking toward an outdoor concert that's taking place near the Hotel Nacional, where Al Capone used to stay. I'm nervous that we're going to get stopped by the police, but Pablo says they'll recognize that we're friends. Near a store selling Ray-Ban sunglasses, he runs into another jinetero, a light-skinned man who, like Pablo, has a shaved head. They chat for a while about a pair of Americans they met the day before, and again we're off. Pablo tells me his friend was actually a partner.

In response to the new jinetero rule, which first appeared in January, he and five other men banded together to create a more efficient form of hustling. They held a series of meetings where each person laid out his technique, along with key details such as how to tell when tourists have just arrived or what clothes correspond to which country. These would allow them to form quicker bonds with tourists and thus (they hoped) avoid the police and claims of harassment.

They also agreed to share resources. "I have an advantage because I speak English," Pablo explains. "Someone else, they have a way to get cigars. It's, ah, how do you say it, an organized crime."

As I digest all of this, wondering if it really is an organized crime, we continue our walk down the tree-lined Prado. It's Saturday, and artists are out with their kiosks, selling semi-Cubist water-colored portraits and oils of buxom Cuban women. I ask Pablo how he's making money these days, and his response surprises me: "Tobacco, drugs--whatever people want." When I ask him how he feels about this, given his previous sanctimony, he tells me he was wrong to be so critical. "I didn't realize it would ever be this hard," he says. "You have to do it to survive. Some days I sell 12 boxes of cigars, and things are great. Other times, I don't sell anything for weeks and I'm lucky to sell some marijuana."

Pablo stresses that he's also trying to learn German so he can talk to yet another group of potential customers. He still insists that he tries very hard to "make money without hurting anyone." But it's not easy.

I agree, but isn't there anotherway to earn dollars? What about teaching English? And then, tired of my badgering questions, he suddenly stops walking. He pulls out his wallet.

"OK, you want the truth?" he says. "My real business is women."

Now I'm really shocked. What about all the regrets from the experience with his sister Susanna? Who are these women you're selling?

"No," he says, laughing, tugging at a picture under the billfold. "Women! Look. I have a German girlfriend."

He shows me a folded picture. A woman with wavy brown hair, about 35, stands in a flowered bikini on a beach. Her arms are held over her head, as if to say, "Ta da! This is your prize." And indeed it is. Pablo informs me that she'll be arriving in August to marry him and take him back to Frankfurt. After dancing together one night, after spending a pair of two-month sojourns in Cuba together, they're planning to tie the eternal knot.

I look down at the beige, brand new Fubu boots on his feet--a gift?--and worry about my friend's decision. I want him to stay because, despite his "organized crime," I've become convinced that he could have a positive effect on Cuba's future. I don't have the guts to say this, or to ask how his sister and mother will survive without him, so I simply tell him that it's going to be hard: that Frankfurt is cold and no one speaks Spanish and the music sucks and Germans are legalistic and don't expect it to be perfect.

Through all this, he just smiles. He says he'll come visit me. "It's OK," he says over the din of the salsa music that I know he'll miss. "She really loves me. She's taking care of everything."

Damien Cave ([e-mail]) is a contributing writer for Salon.com and a Phillips Foundation Fellow.

Phillips Foundation fellow DAMIEN CAVE Calls Cuba "the most inspiring and the most frustrating place I've ever been." (See "Havana Hustle," page 38.) Having traveled for six months in South America after graduating from Columbia University's journalism school, he knows what he's talking about. He's now living in Havana, on his second two-month trip to the island to write about the effects of tourism. "In December, I found people remarkably willing to talk," says Cave, on sabbatical from his position as a Salon contributing writer. "This trip has been different-that kind of openness is much more dangerous" since Castro's most recent crackdown on dissent.