The road from Havana’s José Martí International Airport runs through a landscape of lush green and cinder-block gray, of pastels and corrugated metal, and of course a surreal, seemingly endless flow of finned-out, chrome-covered classic American cars. Some look pristine. Others are a shadow of their former glory, chugging along the highway, belching exhaust and running on long-borrowed time. It’s easy to think of Cuba as a snapshot, stuck in the moment after Fidel Castro took power and declared, “The Cadillac does not increase the wealth of the country; it diminishes it.” When the U.S. embargo cut off the supply of parts in 1960, necessity made Cubans into the automotive mad doctors they are today. And the evidence is there just beneath the hood: decades of ingenuity in handmade parts and diesel engines transplanted from Soviet imports, half a century of world history and politics coiled through the innards.

One sees a few new foreign cars on the roads today, a possible sign of a new Cuba lurching toward the future. In December, President Barack Obama announced that the U.S. would renew diplomatic ties with Cuba for the first time in more than 50 years. The announcement followed a hesitant series of reforms implemented by Raúl Castro, who took over as president in 2008, intended to encourage a degree of private enterprise and boost an ailing economy. These have allowed Cubans greater freedom to travel abroad, buy a house or start a small business. In December 2013 the government announced it would allow people to buy their own modern cars without an official permit.

Unfortunately, those cars are mostly Chinese- and Korean-made pieces of shit, my driver tells me. Like the one he’s driving—a yellow Hyundai that skids when it corners, always breaks down and belongs to his employer, the state-owned taxi company. And in a country where the official salary for a doctor was recently doubled to $70 a month, a new import can fetch as much as $250,000. To afford one, he tells me, you must be related to one of the Castro brothers.

It’s the older cars that have brought me to Cuba. Havana has long been home to an illegal drag-racing scene, but a group of participants has recently begun to lobby for official sanction. In a few days they have a race scheduled, a rare public demonstration of a sport whose legal status is still dubious. In a sense, a drag race in Cuba is not unlike its counterpart in America, an arena of reckless teenagers and thrill junkies. Except here, racing entails speeding down bad roads in a jerry-rigged jumble of spare parts spanning five decades. And in addition to cheating death, participants risk running afoul of authorities in a socialist dictatorship that has long viewed their sport as a bastion of counterrevolutionary tendencies. In Cuba, racing is revolution.

Eduardo Hernández and the Missile of El Cerro.

Late on Friday morning, 48 hours before the race, I clamber into a white 1953 Chevy alongside Bent-Jorgen Perlmutt, a 35-year-old American filmmaker in town to film the race and wrap up three years of work on Havana Motor Club, his documentary about Cuban drag racing.

Together we head off into the daily downpour to the run-down neighborhood of El Cerro. We hurry out and under the pitched roof of Eduardo Hernández’s taller, a lofty workshop of gleaming metal decorated with giant Chevrolet insignias. Perlmutt chats up Hernández, joking that he bears a resemblance to Mel Gibson, and Hernández’s wife, presenting them with a stack of U.S. car magazines. Hernández tells us that the U.S. recently rejected his visa application, and he wants Perlmutt to set up a cultural exchange for race car drivers to improve his chances of obtaining a visa—not so he can defect but so he can see how Americans race and what it feels like to drive on good roads. “I watch races from around the world,” he says, “and I ask myself, how do they do that?”

Parked in the taller is Hernández’s 1956 Chevy Bel Air, the Missile of El Cerro. Hernández has dropped the roof a couple of inches, installed two new Chevy doors and moved the engine back toward the driver’s seat, allowing him to lower the hood for a more aerodynamic profile and shorten the transmission, increasing power.

Nighttime at the Malecón, a Havana spot where drivers go to see and be seen.

In the ecology of Cuban motor sports, V8s are the crowd-pleasers at the top of the food chain, followed by Ladas and Moskvitches (wimpy clown cars of Soviet stock) and finally motorcycles, on which Hernández got his start. His family always had a car—his father was a mechanic—so it was a natural transition, cruising around Havana, looking for someone with a car like his to challenge.

Life in Cuba has improved under the new reforms, he says. Before, you couldn’t buy or sell a car, only inherit one. Your car would be yours forever and then your son’s forever. But now in Cuba anyone can buy and sell his own car. (Of course, he says, they exchanged cars before, despite the law; they just had no proof of ownership.)

Just as important, new travel freedoms have opened access to a supply of new parts. A few years ago Hernández was struggling to win races when he couldn’t get his hands on a working carburetor. Now he scours the car magazines to learn what he needs and spends what he has on a shopping list of parts that he asks friends to pick up for him on their travels. “Everything you see, I get it from abroad,” he says. “Dude, I’ve gotten so much better.”

While that access has raised the overall level of competition, it has also increased the performance gap between those with the means to travel and those without. The shift presages the arrival of a new species of racer, one who didn’t grow up in his father’s taller.

A prime example is a newcomer on the racing scene known as Mascara, whose family’s wealth, it is said, is tied to the Cuban tobacco industry. With a supercharged engine in his BMW, Mascara is the rich kid playing with toys no one else on the island has heard of yet. “You can’t compare a new car to an old one,” Hernández tells me. “His BMW, there is no describing what it can do.”

Mascara has even beaten the Titos, a racing clan widely respected for their mechanical prowess and consistent performance. Hernández speaks of them in deferential tones. He does not extend that esteem to Mascara, whose success is merely a function of resources. Mascara may be a sign of things to come, a day when Cuban racing is dominated by rich kids with superchargers. But by then, Hernández says, maybe those guys will have their own exclusive category in which to compete against one another. “People who have more can do more; that’s obvious,” he says. “I don’t have much. But if I have something, I’m going to fight for it, fight for what’s mine because I love it; it’s in my blood.”

One day, Hernández hopes, racing will be truly legal, an official sport. Then he will turn over the keys to his son to race—at a proper venue, with safe roads and that liquid he’s heard about that’s sprayed on professional tracks so the cars don’t skid all over the place. But that’s just what he hopes, he says, not necessarily what he expects will happen.

Hernández thought things would be different after January 2013, when the first officially sanctioned race since the revolution was held. But authorized races are still too few and far between. He’s tired of racing clandestinely, like a fugitive in the streets, worried about going to jail or losing his car if he gets caught. Racing is an addiction, he says, comparing himself to an alcoholic who knows he’s drinking himself to death but can’t stop.

Hernández recently discovered a problem with his camshaft and has been working all week to be ready for Sunday’s race, making his replacement parts by hand. That’s normal, though. He still hasn’t finished construction on his house, because he spends all his free time working on his car. “I only go inside to take a shower and sleep,” he says. “Racing is a huge sacrifice, the biggest you will ever make. It’s like anything: If you want to be big, then you have to sacrifice a lot. And in Cuba you have to sacrifice twice as much.”

Fidel Castro controlled racing even before he controlled Cuba. In 1958, on the eve of the second annual Cuban Grand Prix, Castro’s men kidnapped the lead racer, Argentina’s Juan Manuel Fangio, a five-time world champion, from the luxurious Hotel Lincoln to protest a sport that bore all the trappings of the decadent capitalist regime the rebels were trying to overthrow. The coup put the revolution on the map internationally, but the race went on anyway, until a car veered off the road at a curve and smashed into the crowd, killing seven, wounding more than 40 and leaving a trail of what looked like broken toy soldiers in its wake. By January 1959 Castro’s revolution had toppled the Cuban government.

Street scene in downtown Havana.

After the revolution, professional sports were banned in Cuba. Castro championed amateur sports as “the right of the people” and no longer the pastime of the wealthy. Today billboards on Havana’s streets celebrate sports as a gift of the revolution and athletes as “champions of the people.” But that propaganda pointedly excludes auto racing, which was never brought under the auspices of the new sports ministry.

The official argument is that racing is too dangerous, an argument that is not without merit. As Hernández was leaving one event, his car’s accelerator stuck, forcing him to swerve into a tree to avoid running into a large crowd. The collision uprooted the tree and left three people in the hospital. But racers say there is also a loaded political dynamic at work in a country where the socialist regime still considers racing an elitist pastime.

As a result, a Cuban street race is often an impromptu affair, carried off before a large crowd can form and draw the attention of police. Even so, Perlmutt says he’s seen cops look the other way, even filming races on their cell phones, as the “pilots” pull over alongside the highway while an observer sets up at a makeshift finish line to record who wins.

It’s Friday night, and the racers have gathered not for a race but for a screening of a near-final cut of Perlmutt’s documentary. This takes place in a Polynesian-themed bungalow on a dark hillside far from the lights of central Havana, even further removed from the present. Decorated with tiki masks, nautical paintings and a pair of cattle skulls, it looks like a place Richard Nixon’s corpse might throw a birthday party. The event starts at half past seven, but the racers turn up at their leisure, piling out of cars loaded with friends, family or jevitas (mistresses), greeting one another and fishing beers from a well-stocked cooler.

Noticeably absent is Carlos Alvarez, the driver and mechanic for El Porsche, a Porsche 944 that belongs to Saul, who lives in Miami and is viewed with some resentment as another rich Cuban expat. On Sunday, ignoring Saul’s directive, Alvarez went up against Hernández. The engine overheated and El Porsche broke down. Word arrives at the screening that Alvarez, who was assumed to be out of the race, got Saul’s backing to buy the part he needs and will likely be working through the night.

After a short introductory speech from Perlmutt—in rapid-fire Spanish with little regard for grammar but an abundance of body language—the film begins. It opens with what will prove to be its most controversial scene. A short, scrappy, tragicomic character named Jote Madera pushes a 1951 Chevy Coupe, the Black Widow, into a garage and drops in a new engine. Madera tells a story: It’s an American-made motor that found its way into a boat used to smuggle Cubans off the island; the boat ran aground and was seized by the Cuban Coast Guard, who tossed the engine overboard (presumably as a deterrent to other smugglers), where it was salvaged by a scuba diver, who resold it to Madera.

Carlos Alvarez attempts to fix the engine of El Porsche.

Perlmutt was nervous about the scene. A much earlier cut had elicited a few objections, which he understood to be about his disclosing where racers find engines—a trade secret. This time the scene is greeted with stiff silence and discernible fidgeting.

The mood changes with footage of a recent race. A potbellied older man stands in front of two cars to signal the start. He whips his arm downward, and Madera and Hernández peel off, speeding away from a few dozen cheering spectators who line the road. A camera in the passenger seat of Madera’s car captures his focused scowl, a blurring backdrop of trees and cloudless sky, and the angry whine of a motor.

Hernández quickly overtakes him and wins by more than a car length. But it’s Madera, exuding recklessness, who steals the scene. “You’re crazy,” another driver yells at him. “Don’t you care about anything in life?” In the next shot Madera declares he’s a “raft hopper” and will soon set sail for Florida. “People are afraid of the sea, but it’s easy,” he boasts. “Christopher Columbus and all those guys did it.”

Alvarez’s garage.

Part of the film focuses on 2011, when a group of racers attempted to get sanction for the first official race in 50 years. At one point they had a date scheduled. Three days before the race—officially dubbed an “event of maximum acceleration”—it was called off. At the time, Ernesto Dobarganes, president of the Cuban Federation of Motorsports, gathered the racers and read a formal letter announcing its suspension, without stating a reason. According to Perlmutt, Dobarganes asked him to turn off his cameras and explained the race was canceled because Pope Benedict would be making his first visit to Cuba and authorities needed the barricades.

Perlmutt didn’t understand, since the race would be far outside Havana, where the Mass was to be held two weeks later. Then he learned the pope’s visit would require all the barricades in the whole cash-strapped country, and these were in such poor condition they first needed to be repainted.

Dobarganes plays the part of the hesitant bureaucrat. In a televised interview, he explains that the race will eventually go forward when organizers have secured all the appropriate levels of authorization. When asked what would happen if it doesn’t pan out that way, he outlines a less than audacious response. “A very simple thing would happen, and it is a direct message to all the TV viewers,” Dobarganes deadpans, staring into the camera without a hint of irony. “We would keep waiting for it.” Eight months later, they finally get their race.

After the film ends and the applause dies, a discussion follows and gives rise to a heated debate over one short but powerful anecdote. Driver Rey Lopez begins it, complaining that Madera’s story paints a false and unflattering image of Cuba. “Now, if he wants to grab a raft and leave the country, it’s his life,” he says. But Lopez takes issue with Madera’s facts, specifically that anyone would throw an engine into the sea.

In the ensuing debate, some agree with Lopez. Others defend Madera, arguing that his story speaks to an important facet of life for some Cubans that should not be overlooked. But no one seems to believe the story about the engine.

“That’s a lie. Nobody does that here,” says driver Lorenzo Monnet. “Everybody gets an old engine and replaces its parts one by one until it’s put back together. There’s no other way to do it.”

It’s a wrinkle that merits looking into. But there are signs of an even more pressing problem brewing when Perlmutt catches sight of Dobarganes talking conspiratorially in a corner of the room with the president of one of the car clubs. When he asks what is going on, Dobarganes reassures him that everything is fine. No one is reassured.

It’s the day before the race and nothing appears ready. Rey Lopez claims that everything is set, but parts of his engine are visible, neatly organized on the floor of his shop. Worst of all, there has been no confirmation from Dobarganes that the race is even on.

Rey Lopez and his brother Jose Miguel Lopez are the sons of Reynaldo “Tito” Lopez. The family is widely respected in the racing community, where they are affectionately referred to as the Titos. Wearing frameless glasses and a polo that hangs like a mud flap from his belly, Jose Miguel looks like an accountant coated in axle grease. But the shop behind him is a portrait of order, with a handful of cars under cover.

Jose Miguel believes racing is doomed always to face resistance. Like other sports associated with money, including hockey, racing is painted with a wide, counterrevolutionary brush. “Except for baseball and the things Fidel always liked,” he adds. It’s a function of the regime’s ideological prism, through which the successful entrepreneur is seen as similarly tainted. “Whenever someone grows, he’s a capitalist.”

Rey Lopez in his garage.

Fidel is one of history’s great political figures, Jose Miguel continues, but not so good at economics. “Before, there were people who were very poor, a lot of beggars, and the revolution helped these people,” he says. “But there were also people who were very well-off, because they had shops.” His grandfather, for example, whose plan to launch an auto service center was derailed by the revolution. His grandfather always said it was one thing to nationalize the big wealthy enterprises, but he knew when the government began to target smaller businesses that the economy was in trouble.

In 1999 police showed up here at his family’s home to investigate their thriving mechanic business. On the basis of a paperwork error, he says, their business license was taken away. Jose Miguel offered to fix the glitch, but an officer told him the decision had already come down from above. The family continued to work until he, his father and his uncle were tossed into jail for a night, then released without explanation.

With the family name stigmatized, Jose Miguel and his brother left for Italy to work as mechanics at a brother-in-law’s transport company. Their room and board was covered, and they earned more than $1,000 a month, a fortune by Cuban standards.

It was a learning experience to work in a capitalist society. He recalls the first time he heard a co-worker criticize a head of state, saying, “This Berlusconi is such an asshole.” Jose Miguel whips his head around in simulated shock. He struggled to explain to Italians how one could live in Cuba while earning $10 a month. “We’ve been living like this for 50 years,” he says. “We don’t go hungry. We survive.”

He also saw the flip side of capitalism when Italy’s economic crisis hit and truck drivers clamored to get paid so they wouldn’t be thrown out of their homes. In Cuba he didn’t have the luxury of living however he pleased, but neither would anyone toss his family out because he couldn’t pay the bank.

Today Cuba is asking too much of a people unaccustomed to capitalism to move so quickly into a new system. People are scared. Everything you can get a license for is now taxed. A year ago, maybe you paid 200 pesos a month for a license to sell sunglasses, but you made 1,000 pesos or more a day. That was too little, but now the state charges too much. As Jose Miguel sees it, Fidel’s revolutionary focus on equality of outcomes cut too broadly, bringing the beggars up but the entrepreneurial class down, while Raúl’s reforms have been too swift.

A driver putting full throttle on his car.

And the state has proved recalcitrant in relinquishing its grip. A few years ago people began to build theaters in their houses, investing in seats, air-conditioning and 3-D televisions. Overnight a law was announced prohibiting the practice. The official reason stated in the newspapers was that these private theaters were showing porn flicks. “That’s absurd,” says Jose Miguel. The same thing happened with the satellite-television cooperatives. The real reason behind the crackdowns was the fear that Cubans were being exposed to counterrevolutionary ideology.

Still, things have changed significantly. He asks if I know “los Beatles.” In the 1970s he would have been arrested for playing the Beatles at a house party. Today Havana is home to John Lennon Park. No one expected much to change under Raúl, but things have. Today on a TV show called Cuba Talks, on which respondents had previously been instructed how to answer preprogrammed questions, random people are interviewed on the street and are freer to express an opinion, even to criticize policy. “We grew up with this fear, and some people are still afraid. But many people speak up,” he says. “The whole world has to evolve.”

Just then, word comes that the race has been canceled.

In Cuba, getting to the bottom of a bureaucratic decision is difficult. It is especially hard since I’ve come in under the radar, without an official journalist’s visa. Dobarganes’s explanation essentially centers on a minor political turf war: A local official, miffed because another official had signed off on last week’s race without consulting him, refused to sign off on this week’s race. Later we hear a rumor that the necessary approval could not be secured because the venue’s manager had just defected to the U.S. Dobarganes, who had assured Perlmutt this week’s event would happen, had pleaded with the racers not to go through with the previous race, because he feared such an outcome. But the racers had decided to race anyway: The stars so rarely align for them that waiting one out was a luxury they felt they couldn’t afford.

Several of the racers blame Dobarganes, a former pro racer who was in the prime of his youth when the sport was taken away from him. Today Dobarganes is a government man of sorts. I have plenty of questions, but when I cornered him at the screening, he promised me an interview the next day, which he then postponed and will postpone every day until it’s time for me to leave—a common tactic, says Perlmutt.

These bureaucratic tangles may explain why real reform has yet to impact the average Cuban. Hal Klepak, a professor with the Royal Military College of Canada who researches the Cuban military, believes the ongoing reforms “may seem slow by the standards of Brussels or Washington, but by the standards of Cuban reform, they’re absolutely exceptional.” Klepak says the government is hampered by resistance from the Cuban bureaucracy. Raúl Castro has the loyalty of the military, but bureaucrats within the Communist Party and the civil service drag their heels when implementing reforms that come from above. “It’s the state bureaucracy and the Communist Party bureaucracy that have learned to live with the difficulties and have their little advantages that bureaucracy and bureaucrats always seem to get,” says Klepak. “Here those advantages are really quite extraordinary.”

To find Jote Madera, we have to travel to the outskirts of what can still be called Havana, a mix of town and country that bustles with old cars, packed buses, horse-drawn buggies and hand-pulled carts.

As Perlmutt’s film leaves it, Madera sold his engine to build a raft for another attempt to reach Florida. When that attempt failed, Madera bought a new engine that turned out to be too small to race. He was utterly deflated, and not much has changed.

“Everything is still the same,” he says. “If you come here today, you will see the same thing in 10 years.” He makes good money fixing fenders, but about half goes to food, he says, “and the rest goes to shit—everything here is shit.”

He has attempted to defect three times with his nephew. They got matching tattoos to commemorate the endeavor; he lifts his shirt to show a shark stenciled across his stomach. That makes nine attempts for Madera so far. On his closest try, the U.S. Coast Guard picked him up about eight miles off the Florida coast. (In accordance with the U.S. “wet foot/dry foot” policy, Cubans picked up at sea are returned to Cuba, while those who make it ashore are immediately granted asylum.) On the most recent attempt, a Cuban maritime patrol stopped them. Madera and his nephew had shipped out from the port of Mariel, located at the mouth of the Gulf of Mexico, about 90 miles from the Florida Keys. In 1980 it was the departure point for some 125,000 Cubans fleeing by boat to the U.S.

Jote Madera and what is left of his Black Widow.

Today the Cuban government is constructing a special free-trade economic zone and a new seaport there as part of its effort to draw much-needed foreign investment to Cuba and the world’s largest ships to its deepwater harbor. But the increased activity has brought more surveillance. Madera says they could leave from Pinar del Rio, closer to Mexico, but the currents in the Gulf are more dangerous for a small boat. After his arrest, he spent three nights in jail and paid a fine of around $200. It was a relative slap on the wrist: If you pay to use someone else’s boat, he says, you could get 10 years in prison.

When asked why he is so desperate to leave, he taps his left hand, covered in a bloody gauze patch, and makes a cutting motion across his wrist. A few years ago, his hand grew infected after surgery. The wound still won’t close, and his body no longer seems to respond to the ointment the doctor gives him. With his right hand Madera bends the lifeless fingers on his left, which has the look of a rubbery claw. He exposes a deep, raw divot beneath the bandage. The last time he returned, the doctor told him the only thing left to do is amputate. That was a month or two ago. He hasn’t been back since. “I don’t want anybody touching my hand,” he says.

But Cuba is known for its great doctors. Why not get a second opinion?

“He is one of the best doctors around,” Madera replies. He thinks American doctors could fix it and plans to sell his motorcycle to try once again to leave the island. “I was born to work,” he says. “I wasn’t born to eat shit.”

I tell Madera that some of the other racers said an engine extracted from the ocean would be useless.

Inside Madera’s shop, where he makes fenders and other car parts.

It’s just the engine block, he says. When a smuggler is caught, Madera continues, the police turn his boat over to civilian mechanics to be disassembled piece by piece and the rest dumped at sea. “But the person throwing it out is human, just like you, just like me,” he says. “And they have a GPS to mark where it lands.” It won’t rust if it’s covered in grease before it’s dumped and retrieved within a few days. Madera buys the bare block, which weighs about 40 pounds—less in water, he says, a job two scuba divers could handle together—then outfits it with undamaged parts.

What he really wanted was an aluminum engine block, which costs around $15,000. The salvaged block cost him $300. “What would you do?” he asks.

Madera started by racing motorcycles in his neighborhood. He wasn’t much good at it, so he decided to move up to cars. He had heard that Lopez’s was the fastest car in Cuba, so he showed up at his front door and challenged him to a race. “He said I was crazy,” Madera says. Lopez eventually agreed to help him build his car nonetheless. In his first race, against Lorenzo Monnet, Madera broke his gearbox. “It exploded,” he says. “Boom!” The high point of Madera’s racing career was when he finished second. But that’s beside the point. Madera is clear about why he races. In the film he says, “Racing makes you bigger.” Huddled in the shack, hail pelting the thin walls like automatic gunfire, he just laughs and says, “Losing doesn’t matter.”

I want to experience what David Peña, a respected figure in the racing community, calls “the common denominator—speed.” Monnet agrees to show me. We are parked alongside a straight stretch of road cutting through Cuba’s thick, bright foliage in a red and black Ford Fairlane he’s fixing up for his 16-year-old son. Monnet has a tattoo of a flaming skull on his wrist and a spare tire around his midsection, the result of an ongoing battle with cancer. The interior of the car is stripped and unfinished, giving it the look of a prototype for an Apollo space mission. A pair of dice and a U.S. dollar symbol hang from his rearview. He has removed all the seats except the driver’s, so I’m squatting in back, digging my heels into the floor for traction.

Monnet planned to boycott the race anyway. He’s critical of the federation for not doing more to support the racers, who don’t even get money for gas despite the hundreds of spectators paying entrance fees and the vendors selling beer, the wheels of economic activity spinning all around them. The drivers don’t even know where that money goes. But worse is the constant uncertainty. He works hard to prepare for a race, then it gets “postponed.” Not even canceled, always postponed. Driving is a source not only of release for him but also of renewal. After chemotherapy—a gift of the revolution, as he sees it—he’ll take his wife and son out on the road and come back ready for another round. Racing is in his blood. Most airline passengers sit there worrying that their plane will fall out of the sky, he tells me; he wants it to go faster. He backs up, the engine rumbling with a deep, throaty purr, and shifts into gear.

Then he floors it. We accelerate quickly, blasting past a startled pedestrian along the side of the road. Whether from the air streaming in through the window or the car’s vibration, the light seems to bend in my eyes, blurring my vision. The faster we go, the faster I want to go—to race ahead, push boundaries, escape my orbit. It is a joyfully reckless impulse, whatever it is that drives a boy to take a fast sled down a steep hill.

Before long we are out of road, closing in on a truck headed our way. Monnet brakes quickly and then throws it in reverse. Turning onto a dusty side road, he spins a donut, the tires burning rubber against the sunbaked asphalt.