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Around 2003, Jose joined an email list that circulated among his hacker pals and back-alley electronics sellers around the capital. A few days later, he bought a hard drive someone advertised in one of the emails.
But as the list's users invited friends and family — and computer access slowly spread in Havana — the emails began selling more than just computer parts. Soon cars, services, food, and motorcycles were being hawked. The emails reached hundreds of people around Havana, well outside Jose's group of friends.
"We knew this one black market, for computers and electronics, but we were surprised at how quickly all these other sellers came together," he says.
Jose and Juan decided to organize the email lists by product. One list was for computers, another for cars. But there was just too much. The lists, Jose decided, had become a revolico — a big mess.
So in December 2007, the two friends — both done with college and working as programmers — built a website for all the ads. Jose modeled it on Craigslist, a site he'd studied at the university.
The project was a colossal risk. Jose and Juan were putting a black market on the web and offering Cubans an open forum on the Internet. The site is registered through DomainsByProxy.com, a company based in Scottsdale, Arizona.
Jose says the state didn't approve the site, and he hosted it on servers outside Cuba to minimize the risk of authorities linking him to the site. If he censored political posts, he believed, they might not shut it down.
However, Jose declined to give New Times his real name or to identify his partner. His story is impossible to verify independently.
He clearly never intended the site as an act of defiance. He says he simply wanted to make things a little better in Havana. "Everyone in Cuba uses the black market because you have to. We wanted to make it a little easier," he explains. "At least for those who have Internet."
Sasha Rodriguez squirmed in the thick, wet air of the Havana summer of 1999, her tanned face ghostly in the blue and white light glowing from an ancient monitor. "Isn't it time yet?" she whispered to a friend. Four others who had crammed into the stifling, cluttered room nodded and grumbled.
"No," her friend whispered back. "We have to wait till midnight or it won't work."
A flash of excitement shot up Sasha's spine. The teenagers were breaking not only their parents' rules, but also Cuban law. They'd used even older computers at school to type essays about the revolution, but Sasha's friend, Enrique, a daring boy who was good with computers, had promised something special tonight.
Just past midnight, Enrique double-clicked an icon and held his hand over the modem. The teenagers held their breath as the dial-up tone beeped, clicked, and hissed. But Enrique's parents, snoring in the next room, didn't stir.
"Here we go," he breathed, as the screen slowly loaded a teen chat room.
Sasha held her breath as her friend typed a message on the screen: ¡Hola! ¿Quién está en Miami?
A boy their age named Mike chatted back. He lived in Miami, he said. ¿Como está la Habana?
The friends gasped and laughed. They spent hours in that room, waiting as their tenuous dial-up died and reconnected. They asked their new friend about life in the Magic City. "For me, it was like, 'Oh my God. Miami actually exists outside of my imagination. There are kids like me living there," Sasha says. "It was life-changing."
The chat nearly a decade ago now seems a lifetime away to the erudite 22-year-old Michigan State law student, who left Cuba for South Florida in 2005. (She asked that her first name be changed because she frequently returns to the island to see family.) But it's exactly the kind of experience that has shaped a generation of young Cubans who are connected to the world outside their totalitarian island. It's something their parents and older siblings never knew.
Only about 200,000 Cubans have regular access to the Internet, according to a 2007 study — the most recent available — by the International Telecommunications Union. That amounts to just 2 percent of the population — by far the lowest percentage in Latin America.
Most people log on at schools or businesses, where the web is tightly restricted by censors. But, as Sasha discovered, many young, savvy Cubans have found illegal hookups. Some hack into phone lines or buy legit Internet time from journalists or lawyers who receive state web access and earn a few bucks by selling off the bandwidth.
That's only the latest development in the black market. Sasha recalls its long history in the area she grew up — Ernest Hemingway's crumbling neighborhood, which is now called 10 de Octubre. Her father worked at a state-controlled bakery, and at home her mother made and sold illegal pastelitos, pan, and empanadas to neighbors.
These days, Sasha says, her friends and relatives living on the island have turned to the web for some of the transactions that used to happen on street corners and in living rooms. "My friends are all on Facebook, they're emailing, and they're talking online," she says. "Cuba used to be a place where you connected to your neighbors, your classmates, but that was it. You were walled off. Not anymore."