East Oakland’s Gambit: Playing on the Town’s BIPOC Chess Team

Me warming up for our simul against GM Maurice Ashley

The grand ballroom silenced as the double doors opened to the Northern California Regional Chess Championship in 2005. As we walked to our seats for the first round of competition, one thing was clear: we were the only team comprised of BIPOC chess players. That did not faze us though; Big Buddy prepared us for this moment. This is a story on my time playing on Charles Windsor’s Windsor East Bay Chess Academy (WEBCA), the only competitive Black-founded chess club in Oakland at the time, and the lessons he taught me about what it takes to compete in spaces where not many people look like me or shared my background.

What spurred me to reflect on this moment was actually a Netflix show, The Queen’s Gambit, that one of my best friends recommended to me. Knowing that chess is a big part of my life, Matt suggested I watch the show. Unbeknownst to him, I had developed a very traumatic relationship with chess over the years and would shy away from even thinking about it. However, The Queen’s Gambit was a great show, and actually gave me some therapeutic energy to revisit memories from when I was training on the WEBCA team. More importantly, the show also gave me some closure and healing from the sudden loss of my own Mr. Shaibel – the janitor who originally introduced Beth Harmon, the show’s protagonist, to chess. The loss of my coach Charles Windsor abruptly ended my time playing competitively.

My coach, Charles Windsor

Charles Windsor, or as my team called him “Big Buddy”, was the kind of coach that believed in the heights of my potential much more than my eleven year old self did. Big Buddy was the kind of coach that would have me dig deeper into my mind when I thought I had dug so deep into myself already. I felt his confidence exude and envelope around me while I played the game. Looking back, I appreciate and often wonder where that self-assuredness and confidence came from: was it from his upbringing at Morehouse, or when he became a doctor, or was it when he retired and decided to spend countless days of the week lugging suitcases of chess boards and clocks to kids around Oakland? Wherever it came from, the confidence was exactly what I needed to feel comfortable competing with kids from more affluent teams.

My teammates playing against Grandmaster (GM) Maurice Ashley

Big Buddy always taught us to conduct ourselves on the chess board with a strong sense of cordiality, sportsmanship, and seriousness. Always shake hands with the opponent, say “good luck”, and tap your clock. We were also never allowed to resign a game; even if we made a serious blunder in the game that was sure to make us lose, we always had to play to the end to a checkmate. “How are you sure your opponent will not make a blunder that you can take advantage of?” would be Big Buddy’s common refrain. After the game: always shake hands, say “good game”, sign the tournament results, and reset the board.

We used to play two times a week in person and were encouraged to play a couple hours a day and study from books on our own. On Mondays, we would play at school, and on Fridays we got to meet up at the local Round Table and play rated games while eating pizza. Like Beth Harmon’s character, an intimate connection with the game developed into a sort of home for me and refuge from what the world was going through following the 9/11 attacks in 2001.

Grandmaster (GM) Maurice Ashley giving a speech at our simul

My oldest sister’s partner at the time also satiated my appetite for chess literature and knowledge by gifting me chess books that same Christmas. Together with Big Buddy’s extensive collection, I devoured every book: Pandolfini, Fischer, King’s Indian, middle game theory, any book I could find published by Everyman Chess Co., and my favorite, queen’s pawn opening theory. I played thousands of games on an old online community called the Internet Chess Club, where masters gathered to teach and play. This routine felt like home, giving me a world that was so grokkable, in which I felt like I finally belonged. Our chess academy even invited Maurice Ashley, the first black Chess grandmaster, to come play a simul and talk to us about his experiences playing at the upper echelons of the chess world.

“It’s an entire world of just 64 squares. I feel safe in it. I can control it, I can dominate it. And it’s predictable. So, if I get hurt, I only have myself to blame.”

– Beth Harmon

I can attest to the intensity of Netflix’s depictions of competitive chess. I have never before seen the sheer competitiveness of the game succinctly captured on film like the way that show did. It feels so extremely satisfying to see a sport that I love be portrayed in such a validating way. There is a way about the game that captivates players, devours every synapse in their neural network, and welcomes them into a focused and addicted state of flow. I would highly recommend the series.

Northern California Regional Chess Championships 2005, I am on the right

There is not a day that goes by that I do not think of what Mr. Windsor taught me. Big Buddy gave me the best lesson of all – which was to always believe in myself. That lesson has been an immensely powerful tool in guiding me whenever I have found myself to be the only low-income or Southeast Asian kid in places of academia, politics, or industry where I had never previously seen people of my background occupy. Though he passed in 2004, we continued to play the game and even went to that Northern California Regional tournament later in 2005 as a whole team. I ended up placing 3rd for 9th grade at that tournament.

My friend Danny Tan and I representing Skyline High School in Sacramento

After our chess academy stopped meeting, I decided to create my own chess club. In 10th grade, I applied for a grant from the US Chess Federation to create the Skyline High School Chess Club with my friend Danny. There, I taught the same lessons, books, and strategies that Big Buddy taught me to a dedicated group of my friends. We even sent a team to the Sacramento Chess Championships and won first place! At the end of high school, the Windsor East Bay Chess Academy surprised me with a sizable scholarship, which I was able to use to procure my first MacBook Pro that I used all throughout college.

My chess class at our Buddhist temple

For the past few years, I have been teaching chess at my Vietnamese Buddhist temple’s youth group in Hayward. Due to our beliefs, we have to modify our wording a bit though – for example, we prefer to say we “captured” a piece instead of saying we “killed” a piece. Nevertheless, I feel like I look at my students with the same eyes of confidence as Big Buddy: that though we may be children of refugees, we can be just as good as wealthy players from SF, Berkeley, or Palo Alto. Just having a coach in the room that believes in the heights of our aptitude can mean everything to a young third culture kid who is still discovering the depths of their own potential.