The Rules of the Game: Ernest Levert Jr. helps launch Upper Cup Chess

The next edition of the twice-monthly game days is set to take place at the Olde Towne East coffee shop this Sunday

Andy Downing
Columbus Alive
Ernest Levert Jr. with The Royal Oak Initiative holds large 3D printed chess pieces created by IC3D Printers. Levert is trying to reach all people who play chess and bring the history and strategy of the ancient game to new players.  (Photo by Tim Johnson)

Ernest Levert Jr. said there are three rules for anyone who participates in the twice-monthly chess event he helped launch at Upper Cup in Olde Towne East in late 2020: 1) You need to know the name of your opponent; 2) Everybody needs to take an L, because if you’re not losing, you’re not trying; 3) You need to have fun and commit to growing.

“It’s all good vibes,” Levert said in a late December interview at Upper Cup, where the next chess day is set to take place on Sunday, Jan. 9 (events are held on the second and fourth Sundays of each month beginning at 3 p.m.). “That’s why I’m so big on saying you need to know the name of the person you’re playing, because obviously that rolls into, what’s your background? What do you like to do? We’re really building a lot of camaraderie and community through the game.”

The genial gameday mood Levert cultivates is reflective of the familial vibe the Parsons Avenue coffee shop projects at all times, coming across like a booze-free, caffeinated “Cheers." Twice during our interview, we paused so Levert could warmly greet a friend.

Levert said he started frequenting the shop five years ago, drawn by its inviting confines and the impromptu chess games that popped up both inside and in front of the store, where the lone outdoor table is inlaid with a chess board. “That attracts chess players, seeing people outside playing, people breaking their necks driving by,” Levert said.

So, in December 2019, Levert helped organize a more formalized chess tournament in the space, which attracted a dozen players and proved so successful that he launched the casual Sunday chess game in December 2020, following the initial wave of the ongoing pandemic. Initially created as a weekly event, Levert dialed it back to twice a month in June 2021, with the December event drawing so many folks that a board dotted every table in the cozy room.

“One of my biggest things is making a safe space for learning. A lot of folks steer away from the chess scene, and some people have been traumatized by the chess scene, because it can be so toxically competitive,” said Levert, who also created and heads up the Royal Oak Initiative, a mentoring nonprofit that embraces chess as a means of healing and building community. 

It’s also a more diverse scene than the whitewashed image sometimes associated with the game, which Levert intends to lean more heavily into this year, developing plans for both a documentary and a Black History Month tournament, which will include a visit from Maurice Ashley, the first African American to earn an International Grandmaster chess title. “We’re really rewriting the narrative and changing people’s perceptions of the game,” said Levert, who was born and raised in Dallas, Texas, and relocated to Columbus when he enrolled at Ohio State. “People often think of chess as this super quiet, studious, predominantly white [game], where folks sit in a room for seven hours. And I’m like, nah. That’s if you like vanilla bean ice cream, for sure. But there’s also pistachio.”

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Levert discovered chess in fourth grade, learning the game from his father, who has been playing since the 1970s. Initially, Levert was drawn to the game because it challenged him and gave him something to be good at, which helped to alleviate some of the social awkwardness he said he felt at the time. In middle school, Levert’s father bought him the software program Chessmaster, which the youngster credited with evolving his game even further. Additionally, the narrations on later editions from Joshua Waitzkin, whose early life served as the basis for the movie “Searching for Bobby Fischer,” deepened the life lessons Levert gleaned from the gameplay, with Waitzkin tying chess to various principles and philosophies that existed well beyond the board. 

“When we approach the chess board, it’s really a microcosm of our lives. It’s very easy to be myopic and focus on one area of the board and get blindsided and the bishop comes out of nowhere because you’re too hyper-focused. Some people focus too much on their careers or too much on their religion or too much on themselves and they end up neglecting other areas of their life,” Levert said. “For me, chess represents balance. I was actually playing someone the other day and they didn’t have their pieces set up correctly, so I set mine up and said, ‘Hey, you know, we’re in balance. We reflect each other.’”

Ernest Levert Jr. of the Royal Oak Initiative talks strategy with Nicole Makeda outside of Upper Cup Coffee on Parsons Avenue. The coffee shop is the location of weekly chess tournaments open to players of all abilities. (Photo by Tim Johnson)

There are also elements of self-discovery that surfaced naturally in learning the game, Levert said, crediting chess with helping him more deeply examine everything from his impulsiveness and timidity to his materialism. Over time, Levert has even started to notice the ways his approach to the board reflects his approach to daily life, describing himself as a cautious player who takes a slow and steady view of the game. 

“I have an engineering background, and I was raised by scientists, so everything is pretty methodical, very organized,” he said. “And I do think that has helped me be more patient about how I build things, leaning into community organizing and leaning into youth development. … Chess can be a very powerful metaphor for building community, where each piece represents an aspect that’s required, from consciousness to compassion to creativity, capital, culture and commitment.

"And one of the other lessons we talk about is delegation, right? You have to know the board, you have to know the pieces, and you have to delegate what you want them to do. And it’s cool planting that seed in these young people’s minds, like, you need to know the name of this piece, and you need to know its strengths and deploy it in the right way, because that’s leadership. And when you’re a good leader, people will want to follow you. People will want to work with you.”