Checkmate.
The famed collection of permanent chessboards nestled in a corner of New York City’s Washington Square Park is where tourists go when they want to see what it’s like to lose to a pro. That’s how things go for most people who pay to sit down and play, but it wasn’t the case for Maurice Ashley.
The Jamaica-born chess pro became the game’s first black International Grandmaster back in 1999, which is apparently far enough in the past that his opponent — who immediately recognizes the name at the end of the video — doesn’t realize what he’s walking into when Ashley sits down to play. Their trash talk-heavy game goes quickly and, unsurprisingly, turns in Ashley’s favor by the end. He even catches his opponent trying to cheat at one point.
As Ashley writes in his YouTube video share of this outtake from The Tim Ferriss Experiment, “I was schooled by the best hustlers back in the day! This was actually in Washington Square Park where the late great Vinnie Livermore used to beat my ass at that same table!”
