Beyond the Board: Mentorship, Mastery, and a GSB Legacy

Miles Griffin '19 visited campus to share his story and his journey from the chess board in the Hockenbury library to the professional tournament circuit and his pursuit to be a National Master. His story began as a new ninth grade student at a school where he didn't know anyone else and didn't have a lot of friends.  A self-described introvert, Miles said, "the first month of my freshman year was a little tough because I was trying to find friends and others who were like-minded." That's where the game of chess comes into play. After learning the game at the age of seven and playing for fun, Miles found a space in the library where students could relax and play. It is around this library chess board that he met his "crew".  The three other players at the table became fast friends, teammates, and lifelong chess challengers who made each other better just by playing. 

This group of students became GSB’s "Chess Club" in 2015/16. The club went on to compete in state tournaments where they earned the invitation to travel to Florida for the National K-12 Chess Championship. In December of 2018 the team came home with a trophy awarding them a 2nd place finish overall. The team made up of Mitch Fishbein '19, Lucas Bernui '19, and Miles were now the runners up for the best 12th grade chess team in the country. 

After GSB, Miles studied abroad in Greece as part of Northeastern University's program and later transferred to Connecticut College, where he majored in Physics and Music Technology. Throughout college, chess remained a constant—he competed regularly and stayed close with his high school teammates.

Upon graduating from college, he joined the acoustic division of an engineering firm—starting as a six-month intern and quickly proving himself indispensable, earning a full-time role. Most recently, inspired by his former GSB classmate Mitch Fishbein, a National Chess Master, Miles took a bold step: a leave of absence to pursue mastery in chess. It’s a move that reflects his commitment to growth, self-discovery, and living with purpose—to serve, lead, and to become the best version of himself.

Miles is now traveling the country competing in chess tournaments in an effort to raise his ranking to the level of National Chess Master. To support this endeavor, Miles has also started his own chess instruction business; CHESSQUARES. Through his business he offers competitive rates and flexible scheduling, so students can master the game from the comfort of their own home. While it’s not required, Miles encourages students to learn with a friend—offering 25% off and a more engaging experience. Miles credits his own growth to a friendly rivalry with his high school classmate Lucas, where mutual support and competition kept the game fun and motivating. “Having someone at your level pushes you further,” he says. The 2-on-1 format benefits everyone: students pay less, enjoy the sessions more, and leave with a built-in sparring partner. For newcomers, starting with a friend can make learning chess feel more approachable—and more fun.

"My love for chess started here at Gill with a group of players who are still my closest friends to this day. Without Mr. Prevost’s support, Mr. Wendell approving our trip to Florida, and a Spring Unit taught by my friend and classmate Mitch's father, Alexander Fishbein, a Chess Grandmaster, I probably would not be here today. Gill encouraged me to follow my passion and gave me the space to go as far as I could."

For more information about Miles and his business, feel free to check out his website Chessquares.com.