BOSTON – Nearly a decade ago, Jaylen Brown sat face-to-face with Lawyer Times.
Times, a lifelong postal service worker (and competitive chess player) from Roxbury, was in the middle of launching an educational chess program for students when he got connected to Brown through a mutual contact: the pastor of the Boston Celtics.
The idea of the Future Master Chess Academy – an academy aimed at supporting undeserved youth across Massachusetts – was something that Brown, who has long loved chess, was thrilled to learn more about.
Brown was a young player on the Celtics, Times was a lifelong Bostonian and a diehard fan of the team, and the conversation was thoroughly enjoyable.
“We talked about our missions and our vision – and they aligned,” Times recalled. “He wants young people, especially from underrepresented communities, to use their minds, not just to be thought of as athletes.”
There were no definitive next steps, but it was clear that the two men saw eye-to-eye. Neither knew it at the time, but a critical seed was planted.
Fast forward 8 years, and Jaylen Brown (alongside Jrue and Lauren Holiday) invested $100,000 into the Future Masters Chess Academy through Boston XChange, an incubator he launched last fall to uplift entrepreneurs from underserved communities.
The investment elevated the chess academy so much so that Times was able to retire from his job at the U.S. Post Office after 40 years.
“I’m doing this full-time now,” Times tells me.
How the collaboration between Jaylen Brown and Lawyer Times came to fruition
On a hot June day in the outdoor gardens of the Museum of Fine Arts, I sat across Lawyer Times, separated only by a chessboard. Times recounted how he first fell in love with chess – and how years later, that love allowed him to connect with the Celtics star.
The now-elite chess player grew up in Roxbury in the 1970s in “one of the poorest communities in Boston” and learned to play the game at just five years old.
“My brother, who was nine, was teaching my sister,” Times said. “And that’s how I learned – just by watching. And we played every day. We would play just like the NBA Finals: best of seven. It was so competitive. It was so enjoyable. And I had a great family.”
Thirty years later – and more than 1000 miles south in Marietta, Georgia – Jaylen Brown learned to play the game of chess, too.
Brown was taught by his grandfather, Willie, and, just like Times, he instantly fell in love with the game, devouring book after book about chess, joining his school’s chess club, and competing in local tournaments. (This year, Willie was featured in a David Yurman commercial, playing chess against his grandson).
At Brown’s Bridge camp – an education camp at MIT that his 7uice foundation hosts every summer – we discussed his love for chess, which he credits for making him a better basketball player.
“I wish more people asked me about my chess experience growing up,” Brown told me.
It’s something Brown has brought up on numerous occasions – most recently, in an appearance on Hot Ones a few months after he won Finals MVP.
“One of the best things about my life is that I learned the game of chess,” he said then. “Depending on what gambit, what trap, or what style of play, you’re thinking about the end in the beginning. In life, I like to encourage more to do the same – think about the beginning in the end. What is your mission? What is your purpose? What do you want your legacy to be?”
“You start to play the game based upon how you want to finish it.”
But, Brown also faced some pushback when he first learned the game, as he recounted to Times when they first met.
“[Jaylen] went into a chess club, and he was told that he really didn’t belong there when he was a young person,” Times said. “But every kid belongs behind a chessboard, we believe.”
Brown told me his passion for chess was ultimately interrupted by his booming basketball career. As a middle schooler, he balanced basketball and football practices with chess club, but at a certain point, managing it all became untenable, and chess fell to the wayside.
“I really had some talent for it… Maybe if I were to stick with it, I could have been a really, really good chess player,” Brown told me. “Like really, really good. A lot of people around me wanted me to spend more time and devote more energy to my chess career. But basketball just dominated my life.”
Nearly a decade later, Jaylen Brown’s love for chess became an investment in Boston
Brown’s middle school chess club is only the beginning of the story. In 2024, just a few months removed from his first-ever NBA championship, he launched Boston XChange, an incubator aimed at supporting underrepresented entrepreneurs and creators by providing them with monetary grants ($100,000 a piece), mentorship, and other resources. The XChange partnered with the Jrue and Lauren Holiday Foundation to support ten Boston-based initiatives in its inaugural year.
Lawyer Times, who had been building up the Future Master Chess Academy since his first conversation with Brown, immediately got to work on a Boston XChange application.
“I knew I was a good fit, based upon my conversation with him, but I was just hoping that it would all come together,” Times said. “And it did. We were selected – one of 10, out of 1000s of applications. And I’m sure the fact that we’re an education-based program using chess to help young ones develop their minds caught the program’s attention – and we got the spot.”
That was nearly a year ago.
Since then, the Academy has taken off – now responsible for training hundreds of students in chess from across Massachusetts. It has in-person branches in Ashland and Burlington, as well as a quickly expanding virtual academy centered around making the game as accessible as possible.
“The funding has just been phenomenal – one hundred thousand dollars,” Times said, seemingly still in disbelief. “And the mentorship, I believe, is even more valuable because we’re getting mentorship from Harvard, MIT, Suffolk. And they stay with us. They really are promoting us.”
Angela Times, Lawyer’s wife, said that part of the goal has been to make sure that the Academy is not reliant on just the initial grant.
“They made us think about our business structure and make sure all the ducks are in a row business-wise, from financials to marketing, teaching us how to network, so that way we can be sustainable,” she said.
The funding allowed Lawyer and Angela to recruit many new kids into the academy. It typically costs $1,000 to support a student’s annual chess education.
“That will give them mentorship within our program,” Lawyer Times said. “It will give them a tournament or two a month. And, it will get them materials to study the game.”
The year has come with several pinch-me moments for Lawyer Times
Jaylen Brown hosted the Future Master Chess Academy – alongside the nine other Boston XChange grant recipients – for an intimate dinner at his apartment last season. They sat at family-style tables, and the Holidays and Brown spent all evening getting to know each of the entrepreneurs on a personal level.
“It was phenomenal – just being right there, talking to him once again, talking about our mission,” Times said. “His mind is so next level. And he was telling me about how this is an opportunity right now to really change the narrative in so many ways.”
Brown views chess as an opportunity to hone life skills. He applies the principles of chess to the game of basketball, too, often describing the task of figuring out how to guard other opposing teams’ best scorers as a “game of chess.”
That’s why now, years removed from his chess career, he’s still passionate about getting kids involved in chess. The Future Masters Chess Academy has been a vehicle for allowing others to appreciate the game that’s meant so much, and drawing lessons from the board and applying them to life.
“I like the role that chess can play in developing young minds – getting them to think ahead and think about what’s next,” Brown said. “You’re training your brain – it’s a game, but you’re exercising your brain to think.”
For Times, the partnership with Boston XChange has been career-altering. It’s also been really gratifying – because as a lifelong Bostonian, he really loves the Celtics star.
“I’ve followed Jaylen Brown every day since he’s been here,” he said. “I’m that big of a fan.”
