After a summer hustling speed chess in Vancouver to raise funds for my first visit to Havana, in 2000, I met an antique bookseller on the plane ride over who helped me find an apartment in a magical neighborhood just off the Plaza de la Revolución, where Fidel Castro still delivered speeches that occasionally ran for seven hours. A dignified 81-year-old retired doorman stood guard of the street. After moving from his job at Hotel Nacional de Cuba to the newly opened Habana Hilton, he was on duty when Castro and Che Guevara arrived in January 1959 to commandeer the top two floors for their government headquarters. I quickly made friends with all the families on the street. They took me in with more warmth and generosity than the neighborhood where I grew up. I’d been warned about the poverty in Havana; instead, these people illuminated a poverty of spirit I didn’t know I’d had back home.
I returned to Havana the first chance I could and tried to reconnect with the bookseller. He’d told me on the plane that the only thing that disappointed him about Havana was having to leave it. I found out he’d been granted his wish—cirrhosis took his life and he was laid to rest in Havana’s Colón Cemetery. When I got back to the street he’d introduced me to, everyone else had left too. The doorman had died, and the others had found various means off the island. I asked one of my few remaining friends on the block what I should do. “Resolver,” he said. Figure it out.
I finally found a place in a very different neighborhood: Cayo Hueso in Centro Habana. People in the street led me to a door up the road from a barber shop, caged bird store, and crushed sugarcane juice stand. I knocked and a latch swung open behind a peephole. A dark burly man with swimming-pool blue eyes unlocked the door and held it open a crack. He had as little English as I had Spanish, so instead of embarking on the usual frustrating pantomime negotiations about the room for rent, he held out two upside-down clenched fists and motioned for me to choose one. This is a ritual he’s repeated every time I’ve seen him for the last 15 years.
I pointed to his left fist, and he opened it to unveil a white knight chess piece. He smirked. “Bueno. Usted primera.” I had first move. He invited me up onto his padlocked rooftop, where his daughter brought a small mug of coffee, two shot glasses of Havana Club rum, and a scratched-up chessboard. His loyal dog, Venus, jumped into his lap and he stroked her fur, and over his shoulder was the most beautiful sunset I had ever seen. I gestured to it, and he solemnly pointed to the board before us. Chess, it was obvious, offered him a view more haunting and lovely than any sunset.
Today this gentleman—let’s call him Fernando—and his wife rent a room in their Centro Habana neighborhood on Airbnb. But many years before Airbnb was legal in Cuba and renting rooms to foreigners was subject to fines and even seizure of property, he provided for his family by secretly leasing a room on the roof of a four-story walk up.
Fernando has Chinese, Spanish, African, and German blood, and it seemed to inform all the features of his face with a noble and almost magical harmony of purpose: getting me to play one more game. On the streets below us, amidst cigar smoke and diesel fumes, the slap of dominoes was heard well into the night, while Fernando and I were invariably playing chess up above. His chessboard was always waiting on his roof, freshly reset with pieces or, more likely, frozen where a game was left off. Up there, Fernando also read from one of a dozen books reliving the games of José Raúl Capablanca, his beloved hero and Cuba’s greatest chess champion. It was Fernando who introduced me to Capablanca. I was obsessed with Bobby Fischer, but for Fernando there was only one gran maestro, not only on the chessboard, but as an artist, a scientist, a philosopher.
Fernando has a booming voice that dipped into a panicked hush for only two men: Castro and Capablanca. In all the years I’ve known him, he’s never mentioned Castro by name. Instead he motions by grabbing an imaginary beard or simply refers to “Him.” Capablanca receives the same treatment for entirely different reasons. His genius was mystical. “Capablanca,” Fernando whispered, “was born in 1888 in Havana to a Spanish army officer. That was the only ordinary thing about him.” He held the title of world champion from 1921 to 1927 and is regarded as one of the great artists of the game. “But he was bigger than the game!” Fernando assured maniacally. “The Yuma at Time magazine put him on the cover in 1925. Brinicito, do you know the other men who were on Time magazine that year? Winston Churchill! Charlie Chaplin! Leon Trotsky! John D. Rockefeller!” He lost only 35 games in his entire professional career, and upon dying in 1942—while watching a chess game at New York’s Manhattan Chess Club—his body was sent back to Havana and honored with a state funeral.
Chess had arrived in Cuba more than four centuries earlier, aboard Columbus’ Spanish ships in 1492, and while the shackles of colonialization were broken with Cuba’s revolution in 1959, chess’ hold on the island nation has proved considerably more durable. They joke in Cuba that what King Midas was to gold, Castro was to politics, but Fernando likes to remind me that chess is 1,500 years old and will be around long after communism or capitalism. “Like a great book that never finishes what it has to say, chess is no closer to being solved. It only gets more beautiful as people try in vain. Just like life off the board, we all resolver.”
Resolver—“to resolve” or, colloquially, “to get by”—remains one of the most vital words in the Cuban vocabulary. Considering the new and unknown challenges ahead for Cubans, perhaps it’s not surprising that chess has never flourished more.
The last time I’d seen Fernando was during Barack Obama’s March 2016 visit to the island, the first time a sitting American president had done so in 88 years. In November, I watched from back home in New York as the island experienced an even bigger political disruption: the death of Fidel Castro, who had inhabited the island like Moby Dick in a goldfish bowl. In January, I wrote Fernando to see if he would help me dig deeper into Cuba’s chess history. I wanted to understand its relevance to today’s culture, and how it might illuminate the tidal waves of change on the island. He wrote back and suggested we begin at the Capablanca Chess Club, the first place he went after his own father could no longer give him a decent game.
Before leaving for Cuba, I met with Bruce Pandolfini at a diner near his Manhattan home. Pandolfini is one of the most sought after—and probably the most famous—chess instructors in history. He served as the Manhattan Chess Club’s executive director from 1984 until 1987. “Capablanca was called invincible,” Pandolfini told me, wiping coffee from his mustache. “Capablanca always claimed his brilliance lay in intuition rather than calculation. It was almost supernatural.”
Stories about the genesis of Capablanca’s genius all have the same basic coordinates regardless of the storyteller, but every version blossoms with unique awe. Pandolfini told of how, at 4 years old, Capablanca was watching his father and uncle play one afternoon. His uncle went to the bathroom, and Capablanca notified his father that his uncle had cheated with his knight. (Capablanca maintained an obsession with knights all his life, and no other player has ever been more of a magician with them.) His father didn’t believe his son knew how to play and challenged him to a game. According to some, Capablanca played his father to a draw. “There are so many myths,” Pandolfini said, laughing. “They all take on a life of their own.”
Pandolfini brought along private artifacts given to him by Capablanca’s late widow, Olga: unpublished photos, a letter, Capablanca’s personal Cuban National Bank book with a lone deposit for $6,000 from his winnings on December 23, 1941. Pandolfini also showed me a prized book of Russian chess openings that a teenaged Bobby Fischer had once carried all over New York for a year. Midway through the book was Fischer’s clunky and strangely printed signature: “BOBBY” in all caps and “fischer” lowercased. In 1965, when Bobby Fischer was denied entry to Cuba for the José Raúl Capablanca Memorial (the Bay of Pigs invasion had increased tensions between Cuba and the U.S.), Fischer competed in the tournament by telex from inside the Marshall Chess Club in New York. Pandolfini relayed Fischer’s moves while José Raúl Capablanca Jr., Capablanca’s only son, did the same for Fischer’s opponent in Havana. Fischer lost, and the following year he was granted entry to Cuba and competed in several exhibitions on the island, including one against Fidel Castro. (Castro won.)
“Olga always believed in reincarnation,” Pandolfini told me while repacking the artifacts in his leather bag. Paul Morphy, the greatest player of his era, died in 1884, and Capablanca was born four years later. Olga believed Morphy’s spirit entered her husband’s body. Capablanca died in 1942, and a year and a day later, on March 9, 1943, Fischer was born. “She was certain Capablanca’s spirit went into Bobby’s genius,” Pandolfini said. “For her it was all a continuation. Fischer always adored Capablanca’s games. When he played the match on telex during the Capablanca Memorial in Havana, he played on a table Capablanca had donated to New York.”
After landing in Havana in March, a ’57 Chevy taxi takes me from the airport past the Plaza de la Revolución, where murals of Che Guevara and Camilo Cienfuegos climb several stories across a pair of buildings. All the driver can talk about is the local taxi strike. Queues of stranded commuters are gathered all along the highway, and their ranks increase as we edge closer to the heart of the city.
We swing past the gates of Colón Cemetery, where Capablanca
is buried, his grave marked with a white queen chess piece. Fernando brought me to the grave after our first handful of games. Vendors sold paper funnels of peanuts outside, and Fernando bought a half-dozen for our tour. “Peanuts everywhere,” he said, tossing a handful into his mouth. “Yet peanut butter has yet to be discovered on the island.” It was one of a thousand paradoxes he navigated every day. He worked at a hospital full-time but had struggled to support his family until he began renting out the spare room in his apartment. He hated the risks, but what choice was there? He introduced me to the chess term zugzwang, a situation in which you’re forced to move but every available move puts you in a worse position. “Resolver,” he said, shrugging.
Driving into town, it’s clear that all of Havana is dealing with change. For years, Cuba’s connection to the outside world via the internet has been miserably limited and terribly expensive. Now the government sells one-hour internet cards for 2 Cuban pesos, which are snatched up by entrepreneurial locals and scalped with a 50 percent markup. Cellphones were once rare; now they are as ubiquitous in Havana as any other major city. (When the Rolling Stones played the largest concert in Cuban history just after Obama left last year, what amazed me more than the estimated 500,000 people in attendance was how the audience experienced the event: behind a phalanx of iPhones. Just like everywhere else.) Wi-Fi locations all over the city are filled with clusters of young Cubans nodding off into the glow of their phones. Of the 30 friends I made who were around my age during my first trip to the island in 2000, only five of them remain in Cuba. The rest started new lives in Miami, Spain, Austria, Canada, and elsewhere. While pawns are the most vulnerable piece on the chessboard, they are also the only piece capable of transforming into something entirely new, provided they make the perilous journey across the board.
I drop off my things and catch a cab down to the Malecón, Havana’s famous boardwalk, where Fernando is waiting to join me at the Capablanca Chess Club (just down the hill from the Hotel Tryp Habana Libre, where the first Capablanca Memorial was played in 1962). When I climb out of the cab, a wave crashes over the seawall and splashes a bicycle taxi carrying two tourists in the backseat. I greet Fernando, who’s carrying a chessboard under his arm, and he tells me he’s arranged a meeting with José Antonio Hedman, one of the professional players who works with children at the club. “Do you know where the money came from for the first Capablanca Memorial tournament?” Fernando asks.
“Che Guevara raised the money. Later on, he regularly played against visiting grandmasters. Even Bobby Fischer. Che’s father took him to a tournament when he was a boy growing up in Buenos Aires, and he saw Capablanca playing. That’s where he first got addicted to chess and also where he first learned about the country where Capablanca came from. Che and the Cuban government invested huge amounts of money to support the game.”
Standing before the entrance of the club, it’s clear that those investments weren’t aimed at ostentatiousness. There’s a large row of pink-framed windows nestled into a cream-colored cement exterior, the paint chipped and peeling from the salty sea breeze. Next to the front door, “CLUB CAPABLANCA” rests above a plaque commemorating the centennial of Capablanca’s birth. The club itself has been in operation for almost a century.
Inside, the mint green walls are mostly bare, save for a schedule of lessons and events and a green-and-white magnetic chessboard hung behind an office desk. Aside from the two club managers’ desks pushed up against one wall and a row of tables emblazoned with eight chessboards on the other side of the room, the club is filled only with sunlight. Somehow the place feels a bit like an abandoned church. Inspecting the green-and-white squares on the wooden boards, I slide my index finger inside the grooves worn from excessive use.
Fernando and I sit opposite Hedman, a painted board between us. “Life in Cuba,” he explains, “is about solving challenging problems. The skills chess offers help us a great deal on and off the board.”
Chess is taught in nearly all Cuban elementary and high schools, and in 2003, universities began offering chess degrees. A year later, with 13,000 players taking on 500 chess masters, Cuba broke the world record for the largest simultaneous chess exhibition in history. In 2008, Cuban grandmaster Leinier Domínguez won the World Blitz Championship. While Domínguez is a long way from rivaling Capablanca’s accomplishments, he’s hovered around the top 20 of the world’s best chess players for some time.
This didn’t happen by accident. After Castro banned professional sports in 1962, huge resources were devoted to making Cuba a global powerhouse in baseball, boxing, and chess. The symbolic value of triumph in these fields during the Cold War paid huge dividends. Cuba went on to dominate Olympic boxing and international baseball, and, for an island of only 11 million people, Cuba has so far produced an astounding 43 chess grandmasters.
Hedman invites Fernando and me to an upcoming exhibition at the Meliá Cohiba Hotel. Some of the children Hedman has worked with at the club, he tells us, are eager to glimpse their chess heroes. Domínguez might even be in attendance.
When I spot Fernando’s taxi approaching the Meliá Cohiba the morning of the exhibition, the driver is frantically trying to dodge a patchwork of sea puddles. Fernando hops out and sniffs around the hotel for the exhibition, but nothing advertises it, so he asks the security guards inside for help. They suggest we ask the front desk. No luck there either. A different security guard approaches and advises us to try the Hotel Riviera next door. Nobody at the Riviera has any clue what we’re talking about, so we’re back to square one in the lobby of the Meliá Cohiba. “Cuba neo,” Fernando moans. Only in Cuba. Just then Hedman taps me on the shoulder.
“You made it,” he says, smiling. “There is good news and bad news I have for you. Domínguez will not be here this morning. However, one of our best gran maestros will be here, Lázaro Bruzón.”
A crowd of equal parts children and adults gathers around the restaurant next to the hotel entrance, and at 8:30 a.m., we’re let inside a surreal room furnished with jukeboxes, 1950s American convertibles, and aging Cessna planes. Dozens of tables surround a stage with a screen hanging over a main chess table—the centerpiece on display.
Hedman approaches with Bruzón, still boyish at 34, at his side. After shaking hands, Bruzón explains he learned chess from a neighbor when he was 7. By 9, he’d devoted his life to the game, and the Cuban government recognized a prodigy in its midst. At 18, he won the World Junior Chess Championship, but now, 16 years later, he explains that he is cutting back on international tournaments. He’s receding from a life perpetually in the orbit of chess, a confession that is accompanied by a mix of mournfulness and relief. “I am immensely proud to have represented my country around the world,” he tells me.
There’s an ease about Bruzón’s demeanor that leaves an impression on me. It’s a stark contrast to the lingering tension and friction felt by elite Cuban athletes in other sports. “Have any of the top Cuban chess players left the island?” I ask Fernando after Bruzón excuses himself.
“None that I know of,” he says. “Chess players who devote their lives to chess probably live much more comfortably here than they would in a different system.”
Which makes sense. I’ve interviewed some of Cuba’s finest boxers and baseball players. In many cases, they’ve rejected the vast fortunes that come with leaving the island and crossing 90 miles to compete in the U.S. While none openly regret their decision, they lead lives much like double-exposed photographs, always wondering how they would have fared if they had left. Over the last 10 years, Cuban baseball and boxing have been gutted by international poaching. But not chess. On top of having their needs looked after, chess players in Cuba are seen as something between an athlete and an artist. They might be more appreciated and respected here than anywhere else.
After turning the matter over, Fernando puts his hand on my shoulder. “We admire la lucha [“the struggle”] as much on the chessboard as we do in the boxing ring. Our lives here have always been a struggle, and approaching that struggle with the courage of a boxer or the cunning and intelligence of a chess player is something that commands our respect. The same rules apply in a boxing ring or on the chessboard or growing up in our crazy system: resolver. Many places around the world are confronted with the same thing. They just don’t have our sense of style.”
After the exhibition concludes, kids still hunched over chess tables, Fernando tucks his chessboard under his arm and suggests we go to Cojímar, 10 miles east of Havana, where he grew up and first learned to play. We catch a taxi on the Malecón and head toward the lighthouse. Just before we plunge into the shadowy-yellow glow inside the eastbound tunnel out of Havana, I watch as fishermen cast their lines toward Miami and a gigantic cruise ship enters the harbor.
When we emerge on the other side, very little civilization remains. We close in on a spooky unguarded tollbooth, beyond it only palm trees and giant street lights outstretched like a diver’s arms before takeoff. We pass a stagnant-looking stadium built for the Pan American Games 25 years ago, a paint-chipped mural of Che staring out from inside of what looks like the upside-down ribcage of Jonah’s whale. Soon after, Fernando taps the driver’s shoulder from the backseat and we walk the rest of the way into his village.
As we wind through the outskirts of Cojímar, the sea comes into view and we spot the long wooden pier that was once home to Ernest Hemingway’s boat, Pilar. Near the pier is the Torreón de Cojímar, a battered fort built in 1649 to protect Havana.
A bus of tourists pulls in to visit La Terraza, Hemingway’s favorite local restaurant, but Fernando’s spot is a laid-back rooftop restaurant on a nearby backstreet, perched above a Dalí-like set of stairs. When we arrive, a local boy is posted in front of the stairs, holding a varnished wooden object the size of a sunglasses case. He holds out the box and asks in English if I’ve ever seen a “romance box” before. I shake my head, and he smirks and seamlessly pulls it apart, holding out both halves of the box with his arms spread wide. He brings the pieces back together and effortlessly repeats the gesture once more. “I’ll give you 30 seconds with it,” he tells me. “If you can open the box, it’s yours to give to the one you love. If you cannot open it, then you must pay me 10 pesos to keep it.” He quickly opens and shuts the box again with a blurring sleight of hand. “See how easy it is?”
I glance over at Fernando, but he’s too busy staring at the boy to offer any counsel. So, gullibly yet determinedly, I play the sucker. “¡Vamos!” he says, staring at his watch. I feverishly work the thing over like a Rubik’s Cube until the boy hollers, “¡Tiempo! Diez pesos por favor.” I absentmindedly hand the box to Fernando and fish my pockets for the boy’s fee. When I fork it over, the boy is no longer paying attention to me. He’s staring at Fernando, who is calmly repeating the boy’s opening and closing demonstration.
“How?” I gasp.
“I had the same job here when I was his age,” Fernando says. “But”—and he suddenly switches over to Spanish—“when I saw a girl I loved at first sight, I asked her for something more if she couldn’t solve the romance box in 30 seconds.”
“What?” I ask.
“I asked her to go on a date with me. But first I wrote a secret message and put it inside the box. When she couldn’t open the box, we went on our first date and I gave her the box as a gift.”
“What did you write in the note?” the boy asks. His swagger has left him.
“I asked her to marry me.” He laughs and passes me the box, freeing up his hands to dig through his pockets for a black and a white chess piece. He holds them in his clenched fists and motions for me to tap one, but the boy interrupts.
“What happened to the girl?” he implores.
Fernando ignores the question and grunts for me to choose a fist. I do, and Fernando holds out a white queen in his palm.
“Did you ever see the girl again?” the boy asks deliriously.
“Of course I did. I saw her this morning, when I cooked breakfast for her and our daughter.” Fernando turns and winks at me. “Resolver.”
(Editor’s note: An earlier version of this story said José Raúl Capablanca won every world championship from 1921 to 1927, when in fact he just held the title for those six years. We regret the error.)