GM Maurice Ashley, the first Black grandmaster in history, said he fulfilled a lifelong dream when he appeared on The Oprah Podcast, sitting down virtually with Oprah Winfrey for a conversation about chess, impact, and hidden potential.
Few grandmasters have drawn as much attention beyond the chess world as Ashley. Since making history in 1999, he has become one of the game’s most recognizable ambassadors, both as a celebrated commentator and as an advocate for chess as a tool for personal growth.
In 2024, Ashley released Move: Life Lessons On and Off the Chessboard, a book exploring the principles chess has instilled in his life, which went on to reach Amazon’s bestseller list. Having previously appeared on CBS Mornings, the interview with Oprah Winfrey was a huge personal moment.
The episode centered on a new book by renowned organizational psychologist and professor Adam Grant, whose prologue highlights Ashley’s work with young chess players in Harlem, New York.
The grandmaster was introduced by Grant, who spoke at length about the prologue of his book, which spotlighted the Raging Rooks, a group of Harlem children who, under Ashley’s guidance, rose from being widely underestimated to becoming national champions.
“It’s an extraordinary story on so many levels,” Grant said. “It’s a great underdog story, Oprah. But that’s not the part that resonates most with me. What resonates with me is their secret weapon: their coach, Maurice Ashley.”
Asked by Winfrey what first made him fall in love with the game, Ashley responded passionately, “Chess is magical. It really just is,” he said.
Chess is magical. It really just is.
—Maurice Ashley
“It’s been around for 1,500 years. The pieces themselves are epic and mythical: kings, queens, bishops, knights, rooks, pawns. It’s a reflection of a world long gone, with this historic and mythical quality. And then there’s the complexity of it. It’s a puzzle inside an enigma, one you try to solve but never fully do,” he added.
“For me as someone who was always after puzzles and trying to solve crossword puzzles or sudoku, or you name it, chess became that thing I could never solve.”
What does Ashley consider the most fundamental lesson chess can offer, Winfrey asked.
“Chess is a game of metaphors,” Ashley responded. “It’s not just about checkmating people. It’s about growth, about respecting the journey, and the character-building qualities you gain along the way. One of the biggest lessons is listening to your opponent. Your opponent is your greatest teacher. When they’re whipping you on the chessboard, you’re getting lessons in real time. And that’s what you take from those lessons, the mistakes you make, the games you lose. That makes you grow and gives you resilience and helps you face adversity.”
One of the biggest lessons is listening to your opponent.
—Maurice Ashley
Now 59, Ashley is increasingly focused on legacy and impact. In 2024, Ashley established the Maurice Ashley Chess Fellowship, aimed at nurturing young chess talent from underserved communities across the United States.
“These were kids many people underestimated, who had potential few believed in,” Ashley said of the Raging Rooks. “But talent, discipline, belief, and hard work changed everything.”
Ashley reflected on the experience with Winfrey in a post on his LinkedIn page: “When I became a grandmaster in 1999, there was one person I wanted to talk to more than anyone, and that was Oprah Winfrey. For whatever reason, that interview never happened, and to be honest, I always had a nagging itch that felt like unfinished business. Incredibly, 26 years later, it finally happened,” he wrote.
One moment during the interview stood out in particular “Seeing Oprah hold up my book for the cameras was a surreal, almost fairy-tale-like moment, having watched her do the same for other authors over the years. It confirmed for me how far I had actually come,” Ashley said.
Seeing Oprah hold up my book for the cameras was a surreal, almost fairy-tale-like moment. (…)
—Maurice Ashley
