Derrick Rose knows heartbreak. From his MVP run in 2011 to the injuries that altered his prime, he has lived through highs and lows on the court. Yet, according to Rose, no loss in basketball compares to how defeated he feels after losing a game of chess.

Rose explained that while he can brush off a tough night in the NBA, dropping a chess match lingers in a way he can’t fully explain. “It’s heartbreaking when you do lose in person,” he told CNN Sports. “Losing in chess is a lot harder than losing in basketball. It’s crazy for me to say that, but I feel like chess is more intimate, I don’t know why. With my friends, whenever I lose early on, or whenever I lose a game, it just gets to me.”

Bridging two worlds

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Rose has gone beyond playing chess casually. Earlier this year, he joined forces with Magnus Carlsen’s Freestyle Chess to host a unique crossover event in Las Vegas called Chesstival. The tournament paired NBA players with grandmasters in a “Head & Hand” format, where the pro chess players called the piece and the basketball stars chose the move. Golden State forward Quinten Post and Charlotte’s Grant Williams were among those who tested their wits alongside some of the world’s best.

Rose himself competed and said he plans to organize similar events in the future. For him, it is more than a side hobby. Chess became a serious pursuit during his playing career, something he admits at times consumed too much of his energy. Even so, he has no regrets. Instead, he credits the game with giving him perspective on choices, patience, and resilience.

“It taught me that every move counts and every choice is an option, and within every option, you have to make a decision,” Rose reflected. He added that the joy comes not just in winning, but in bouncing back. “The fun thing about it is getting your a-s kicked and coming back to the board and having a totally different scheme or style of play. I feel like over the years, I was just moving the pieces, but now I’m able to set up a gambit, or set up a trap. It taught me a lot, and I’m very, very fortunate that I found the game early on in my career.”

From MVP to mentor, Rose’s love for chess reveals another side of his competitive drive. On the hardwood or the board, he plays with passion, and the lessons follow him wherever he goes.