Grandmaster

James Canty spent years competing in chess tournaments all over the country—from McDonald’s matches to national tournaments, hustling wins wherever he could. The next goal? Becoming a Grandmaster.

WORDS BY DAVID HILL
ILLUSTRATION BY PATRICK LEGER
VICTORYJOURNAL.COM

When James Canty enters the McDonald’s on Chicago’s South Side, nobody takes notice. Perhaps that’s because most of the dozen or so men sitting in the restaurant are concentrating on chess boards, furiously slapping the buttons on their game clocks. Perhaps it’s because Canty, wrapped in tattoos and sporting a hoodie and snapback, doesn’t seem that out of place among these chess players, almost all of them older Black men. Perhaps it’s because Canty doesn’t want anyone to notice him. As he walks past Sedrick Prude, aka “Big Pawn,” who told him about this spot, Canty takes great pains not to make eye contact, or reveal any hint that they might know each other. It isn’t hard since they only met yesterday, across the board from one another at the 2016 US Amateur Team Championship North.

An older man sitting alone at a chess board asks Canty, “You want to play?”

“For money?” Canty says, feigning ignorance.

“Yeah we can play for money. How much?

“Not more than $20. I don’t usually play for money,” he lies. “$20 is fine. Let’s go.”

Canty sits down and adjusts his pieces. After a couple hours and a handful of games against multiple players, he stands up to leave, nearly $300 richer than when he arrived. The regulars begin to realize they’ve been hustled when one player speaks up: “Let’s play five to one for a hundred.”

Five to one means the player would have five minutes total to make all of his moves, while Canty would only have one. It’s a huge handicap for Canty, but he quickly agrees—they shake on it. Canty hits the button on his clock to start the game. He plays at a dizzying pace, zipping pieces back and forth in a combination of lightning-fast calculation and sheer muscle memory.

And just like that, it’s over. Canty wins with time to spare.

“Who are you?” his opponent asks. It’s a question Canty himself has spent years trying to figure out.

James Canty III was born in 1992 in Detroit, Michigan. His father, James Canty Jr., was an avid chess player, having picked up an appreciation for the game, like so many men before him, while in prison. Eight-year-old “Jimmy” picked up the game right away and was able to beat his dad within a year.

Canty attended Bates Academy, a public primary school in Detroit for gifted students. His father encouraged him to join the school chess team where he could study under Detroit chess legend Harold Steen. Canty’s first year was a bust—he wasn’t yet good enough to earn a spot on the school’s team. He was only nine, and many of the top players were already in middle school, but Canty still felt slighted. His father had little patience for his son’s moping. One morning before school his father woke him up early and set up the board. “We’ll play every day,” his dad told him, “until you’re the best on the team.” The following year Jimmy was first board on the Bates Academy team at the national tournament in Tucson, Arizona. Canty played in the under-1250 division, the largest division since most scholastic players are rated under 1000. He went undefeated and was awarded the national championship.

Canty remained the top player at Bates through eighth grade, helping his team win tournaments all over the country. He ascended to expert level before the end of his sophomore year. In 2008 Harold Steen passed away; the next year, when Canty was a senior, he won the inaugural Harold Steen Memorial Cup, a title that put his rating over 2200 and made him one of the youngest black players ever to achieve the rank of Master. His dream was to become the second African-American player to become a Grandmaster.

The leap from Master to Grandmaster is vast. It took Maurice Ashley, the only other African-American to do it, 14 years. And once Canty graduated from high school, he found the world of competitive chess to be far less hospitable than it had been for him as a student. He no longer had the financial support of a scholastic program to travel to qualifying events, and open chess tournaments, which are almost always won by Grandmasters, typically have prize pools under $5,000—barely enough to cover travel expenses for most players. There are no corporate sponsorships in chess, no professional contracts, no big-money prize pools to chase. If Canty wanted to become a Grandmaster, he was going to have to do it on his own dime. His family didn’t have much money, and his college prospects were slim. So he joined the Air Force.

The US Armed Forces holds its own chess tournament every year, but Canty, despite being the highest-ranked chess player in the US Armed Forces when he enlisted, was not given permission by his unit to enter the event. He kept his head down and worked hard, doing technical work while stationed in Atlanta. After leaving the military he stuck around and pursued another passion: hip-hop.

“I wanted money, and there was no money in chess,” Canty says. “The only way I saw to get rich was entertainment.” In high school he made beats and freestyled, but in Atlanta it wasn’t so easy to navigate between the worlds of chess and rap. “I had a lot of connections on the music side,” he explains. “My community didn’t really get the chess thing, though. It wasn’t cool to them.” So Jimmy Canty, young chess prodigy, became Canty Cash, mixtape rapper. He rarely played chess at all anymore. At 21 years old, Canty hadn’t played any serious chess in almost two years. His dream of becoming the next African-American Grandmaster was fading fast.

One February night in 2014, Canty found himself in Woodruff Park in downtown Atlanta, which is “not the kind of place you’d want to bring your family,” he says. But Woodruff Park is home to a chess community, where people gather at all hours to play speed chess, often for money. On this particular night Canty decided to sit down and join them. He beat everyone in the park. Frank Johnson, a tournament player and chess coach from Atlanta, recognized Canty. Johnson pulled him aside.

“What are you doing? Why aren’t you playing tournaments anymore?”

“I’m taking a break.” Canty replied. He told Johnson that he couldn’t afford to play chess at a high level anymore. Johnson told Canty he couldn’t afford not to. “You need to check out this Millionaire Chess thing,” Johnson told him. “You could win it.”

Millionaire Chess is the brainchild of Grandmaster Maurice Ashley and Amy Lee, a Canadian entrepreneur who met Ashley at a leadership seminar. The Millionaire has a $1,000 entry fee (far higher than even the World Open’s entry fee of $350) and a prize pool of $1,000,000— double the previous record for a chess tournament prize pool. Ashley and Lee are trying to raise the profile of the game, attract sponsors, and create some excitement. Like Canty, Ashley had struggled with making a living in chess after he became a Grandmaster at the age of 33. The Millionaire, held in Las Vegas, is an attempt to inject some adrenaline into the heart of a dying game.

Canty looked at the prize structure and his eyes bugged out—this was real money, life-changing cash. And Canty saw that he had a legitimate shot at getting a chunk of it.

He set up a GoFundMe page to raise the entry fee and travel expenses, and used social media to solicit donations. The only thing left to do was to practice—the tournament was in eight months.

Canty borrowed some chess books from Johnson. He sold his Xbox and TV. “It hurt, but I had to do it. I can have chess or I can have fun. If I want to win this money, I can’t have both.” Like the summer before fifth grade with his father, he dug in and did nothing but study.

Canty showed up in Vegas in October 2014 an anonymous, unrated player in the open division, 10 years removed from his scholastic national championship. He lost his first round. In his second round he was paired up against Ylon Schwartz, an International Master who’s made over a million dollars in poker tournaments. Schwartz, after arriving a half-hour late to the match, sized Canty up as an unrated amateur. Canty quickly realized that Schwartz had played him to a draw.

“Do you want a draw?” Canty asked.

“No, let’s play.” Schwartz replied, annoyed. The game continued, and eventually ended in a draw. Schwartz seemed surprised. “Who are you? What is your rating?” Schwartz asked.

“Well I used to be a Master,” Canty said.

“If I knew that I’d have taken the draw!” The two men met again later in the tournament; Canty defeated him.

Canty won three of his next five games. The next day, as he boarded his plane back to Atlanta $20,000 richer, he had an epiphany. “I’m in the top one or two percent of chess players in the whole world,” he thought. “I have a chance to make history.” Canty recommitted himself to the goal he set when he was in high school. He would make Grandmaster.

At the end of 2015, Canty moved back to Detroit. He called Grandmaster Roman Dzindzichashvili, the author of one of his favorite chess books, and asked if he would be his coach. “He looks kind of like Ron Jeremy,” Canty says, “but he’s cool. He calls other Grandmasters soft.” Dzindzichashvili is a former Soviet Union champion, and despite having won two US championships, in the 1980s and ’90s Dzindzichashvili made his living hustling chess in Washington Square Park. Now a renowned teacher, his services don’t come cheap. Canty used his tournament winnings to pay for instruction from Dzindzichashvili—but only after buying a new Xbox and TV.

Today Canty uses every penny he makes to travel to tournaments. And because his rating is back up to Master level, he often is invited to play in events for free in hopes that it will attract other entrants. In Detroit, Canty has become a celebrated hometown hero. Local kids are excited to play against him, in the same way he was excited to play Harold Steen. He’s even been asked for his autograph. It’s important to Canty to be a role model for young Black players. Almost as important as it is to not be recognized by the older players at this South Side McDonald’s, out here on the road, hustling up train fare back home.

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