Five years ago, this month I returned from three months in Cuba with Goshen (Ind.) College Study Service Term. In honor of the anniversary, I’m sharing this piece that I wrote at the time reflecting on my experience.

I first met Rolando a few blocks away from the Revolutionary Plaza in Habana, Cuba. He was walking a few paces behind two friends and I when he commented on the flower in my friend’s hair. His comments came only as a surprise because they were in English. He took advantage of our response and within a few minutes, he had our rapt attention as he preached against “The Papa” (as he called Fidel) and communist brainwashing from the sidewalk.

The passing traffic was a mix of antique American cars maintained since 1959 and new European and Japanese models that have shown up recently.

Rolando gestured emphatically at the whites in the European imports as he raged against the government of the whites, by the whites, and for the whites. In short, he played the black Cuban dissident to the hilt.

After weeks of walking around Havana, we had come to expect calls of “Cigars? Women?” at every corner. These solicitations came from jineteros, or a middle man for tourists, hoping to pull in a small part of the more than $800 million that comes into Cuba annually through tourism. These men (along with a few women) are children of the special period, which Castro announced when the Soviet block collapsed in 1990. As part of reforms, he legalized the US dollar, eventually propelling the tourism industry to the number one industry in Cuba. Sugar, once the heavyweight of the Cuban economy, has been relegated to a humiliating third, behind remittances from family in the States, an ironic second.

Like antique Fords forced to compete with European imports, Cuban workers still earning wages in pesos are becoming second-class citizens in a classless society. Jineteros offer a risky third way as they pull themselves up by other’s bootstraps, avoiding the trap of low paying peso jobs in the government economy.

Rolando knows the American dream as well as anyone in Cuba. He grew up in Habana, but dropped out of school to work in his uncle’s bakery in his early teens, making extra bread on the side to sell on the black market. His entrepreneurship did not go over well with the Cuban government and he ended up in jail. In 1980, his criminal record came in handy when Castro announced that criminals and other deviants were allowed to leave the island as part of the Mariel boatlift. His life in America wasn’t much easier and in 1999 he was deported back to Cuba for an unnamed offense.

Unlike the many exiles in Miami, Rolando didn’t have any kind words for North American society, where he found himself not much better of than in Cuba.

Upon his return to Cuba, Rolando’s reasonable command of English found a niche in this new economy, at the point naïve tourists and desperate Cubans meet. “Tiene que inventar las cosas” means that you’ve got to do whatever’s necessary to get hard currency. When Rolando wins a foreigner’s trust, he can offer to hook up them up with a wide range of services, from the legitimate end—privately owned restaurants or rooms for rent—to the gray areas—black market cigars and women.

Rolando’s own position is conflicted. He lamented that the government had destroyed society to the point where any women would go to sleep with a foreigner for a price, even as he took advantage of the situation in his profession.

Alberto is Rolando’s alter ego. I first met him at the Capablanca (check) chess club two blocks away from the Florida straight. He quietly trounced me in a game of chess while answering questions about life in Cuba. As a telecommunications engineer for the state corporation, he raises his two children on 700 pesos (or $26) a month. That’s the combined income of he and his wife, a top doctor in her hospital.

With much more at stake in his position, Rolando was understandably less eager to talk than Rolando. Yet over our chess games, I heard a familiar story of the precarious life of a Habanero. It is the story of a Cuban economy squeezed between an embargo and the last idealistic leader in the Western hemisphere. Government rations barely pad a life of essentials in which Alberto and his family have few opportunities for anything but necessities. Of course, the average worker makes only 280 pesos ($10US) a month.

Like Rolando, Alberto is well aware of the alternative. He has foregone the hundred fold salary increase that could await him 90 miles to the north. Locally, there’s the lucrative taxi job with its tips in hard currency from tourists that many highly trained scientists have chosen.

But Alberto has stayed with his skilled job, using his education and training where they’re needed. In exchange, he claims stability, community, and a steady income to support his two children. Like many Cubans I talked with, Alberto talked about the problems of daily life, but did not go so far as to call for regime change. If they did, they would have joined the 3 million that have chosen exile from Cuba since the Revolution 43 years ago.

After our chess game, Alberto offered me a ride home on the back of his scooter. I clung to his back sheepishly as we puttered through traffic lights and got a taste of what transportation must be like for his family. The common sight of families of three and four perched on a single scooter serves is a metaphor for the balancing act that families in Havana must do daily. The nonchalance with which parents balance their children between each other and at their feet on the scooter’s tiny floors can only come from years of practice and nerves honed by Habana’s traffic patterns.

In Habana, Rolando is branded forever as a Marielista, his deportation back to Cuba pushing him to the very bottom of a “classless” society. He makes up what all good Cubans know as the “anti-social element” or those that refuse to go to Alcoholic’s Anonymous meetings or find a steady job in the state economy. Alberto on the other hand, is the new Cuban man, content to work for the good of the community, not putting himself ahead of the needs of society and committed to his family. It is men and women like him that keep the vast state apparatus together, one shoestring at a time.

Yet if Rolando snags two or three paying customer in a night, he can bring in U.S. currency worth more than Alberto’s entire monthly salary. “We have to survive on the streets” was a constant refrain for Rolando, a coda to his apparent callousness, a justification for his vice.

Someday, I’ll go back to Cuba and find him there, quietly napping in the bus stations, sleeping in hospital lobbies and dark theatres.