Grandmaster Maurice Ashley on the Magic of Chess, The Art of Trash-Talking, Must-Read Biographies, and More (#449)

“Once you get to the top of the mountain, you look around, and you get your chance to look. And now what? You’ve got a nice view. That’s great. How long can you stay on the mountain? You need another mountain.”

— Grandmaster Maurice Ashley

Maurice Ashley (@MauriceAshley) made history in 1999 when he became the first African-American chess Grandmaster. He is a three-time national championship coach, author of Chess for Success: Using an Old Game to Build New Strengths in Children and Teens, ESPN commentator, iPhone app designer, puzzle inventor, and motivational speaker.

Maurice is well known for providing dynamic live tournament coverage of world-class chess competitions and matches. His high-energy, unapologetic, and irreverent commentary combines Brooklyn street smarts with professional ESPN-style sports analysis. He has covered every class of elite event, including the World Chess Championships, the US Chess Championships, the Grand Chess Tour, and the legendary “man vs. machine” matches between Garry Kasparov and IBM’s Deep Blue.

Traveling the world as an ardent spokesperson for the many character-building effects of chess, Maurice consults with universities, schools, chess clubs, executives, and celebrities on how chess principles and strategies can be applied to improve business practices and assist with personal growth. Maurice also acts as a master of ceremonies and inspirational speaker at business conferences and high-class chess events.

Maurice has received multiple community service awards from city governments, universities, and community groups for his work. In recognition of his immense contribution to the game, he was inducted into the US Chess Hall of Fame in 2016 and the Brooklyn Technical High School Hall of Fame in 2018.

Please enjoy!

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#449: Grandmaster Maurice Ashley on the Magic of Chess, The Art of Trash Talking, Must-Read Biographies, and More


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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with our mutual friend Josh Waitzkin? Have a listen to our most recent conversation in which we discussed his own relationship with Maurice, approaches to learning, the benefits of being a beginner, why feedback loops are game-changers, unorthodox skill acquisition, and much more.

#412: Josh Waitzkin on Beginner’s Mind, Self-Actualization, and Advice from Your Future Self



  • Connect with Maurice Ashley:

Website | Twitter | Facebook | Instagram


  • The Maurice Ashley origin story. [06:59]
  • Competition runs strong in the Ashley family. [09:55]
  • Why did Maurice’s family make the move to the US from Jamaica? Why did it involve a separation from their mother for 10 years, and what was it like to finally be reunited? [12:02]
  • What neighborhood in the US became home, and how did chess enter the picture for young Maurice? [15:29]
  • How a library book and a worthy opponent changed the way Maurice thought about chess. [18:17]
  • What was the Black Bear School? [19:58]
  • Blitz chess vs. classical chess. [23:25]
  • The Maurice Ashley guide to trash-talking. [25:46]
  • As the youngest member of the Black Bear School, what did Maurice see as the biggest setback keeping his older peers from truly excelling, and how did he evolve after “graduating” from their ranks? [30:18]
  • How did the atmosphere of a venerable chess club compare to what Maurice had, up to that point, been used to? [32:53]
  • Frustrated along the way on his quest to become a Grandmaster, what did Maurice learn from Tiger Woods that kept him in the game? [33:45]
  • At this time, how did Maurice’s frustration and depression around getting stuck in a rut transmute into the inspiration he needed to emerge from that rut? [36:04]
  • How does someone become a Master, Grandmaster, or any title in between? [39:29]
  • After teaching, commentating, and writing, how did Maurice get back into training shape to pursue his Grandmaster goal — and what technological advantage did he have in 1997 that he didn’t have in his Black Bear School days? [42:30]
  • How does Maurice suggest building mental and physical stamina for high-level chess (and why might you be hard-pressed to find a top-level player who could be considered overweight)? [47:00]
  • How does Maurice tie the disciplines of aikido and chess together? [50:38]
  • How did the experience of finally achieving the coveted Grandmaster title hit Maurice? What was the view like from the top of that mountain, and where could he possibly go after that? [53:31]
  • How does Maurice get kids hooked on chess, what does he get out of teaching, and what have been his most memorable teams? [57:02]
  • Why has chess remained popular for 1,500 years –and even seems to be increasing in popularity in the age of COVID-19? [58:31]
  • What would Maurice suggest to a relative chess beginner who doesn’t necessarily aspire to be a Grandmaster, but just wants to become competent at the game? [1:01:37]
  • Using puzzles to expand your repertoire and confidence. [1:03:38]
  • Recommended reading (for chess and general inspiration). [1:05:49]
  • How Maurice is processing the social unrest of 2020. [1:13:29]
  • How would Maurice hope to offset the tyranny of the majority in a way that makes America more just and equitable for all Americans — not just most Americans? [1:19:29]
  • As someone who’s spent time as an educator, where does Maurice feel our current educational models are most woefully lacking? [1:24:40]
  • How nonprofits DonorsChoose and QuestBridge are trying to help provide resources to teachers and students in underserved communities — now even more in need during the COVID-19 pandemic. [1:29:49]
  • Maurice expands on books he was kind enough to mention in Tribe of Mentors as having an impact on him. [1:33:02]
  • On being flexible, embracing uncertainty, and living out of a suitcase (though the timing might not be ideal). [1:39:50]
  • Maurice has never been afraid to say “I don’t know.” So where does salsa dancing, telenovelas, and Pluto fit into all of this? [1:42:09]
  • Parting thoughts and talking trash. [1:49:18]