Retirement clearly hasn’t slowed Derrick Rose down one bit. The Bulls legend has been everywhere—kicking it with fans, teaming up with brands, and now, pouring his heart into something totally unexpected: chess. Yep, D-Rose is deep into the game these days, and not just casually. He’s all in, working on a chess tournament of his own and giving it everything he’s got. And guess what? While we’re all waiting to see what he’s cooking up, he just linked up with the five-time world chess champion at a chess festival. Talk about making moves, literally.
“Chess taught me patience, vision, and how to stay calm under pressure. I want kids who grow up like I did to have access to that,” Derrick Rose once said—and maybe that was his real secret weapon on the court all along. But Rose isn’t just all about basketball. He’s deeply into chess, too. So much so, he once played a game on his phone during a Drake concert. Yup, his wife Alaina once shared a story of him fully locked in on his phone mid-show, deep in a chess game. Rose later laughed it off, saying he only played during a break because he was that bored. That same quiet obsession has now turned into something bigger—Chesstival, a pro-am chess tournament where NBA stars team up with elite players for fast-paced, high-stakes battles.
The Chicago Bulls recently posted some pretty epic photos from Chesstival—Derrick Rose and Magnus Carlsen playing chess against India’s Vidit Santosh Gujrathi and the NBA’s Jeremiah Robinson-Earl in Las Vegas. The caption read: “Find D-Rose at the chessboard @drose & @MagnusCarlsen hosted NBA hoopers & world-class chess player at Chesstival here in Vegas!”—which sounded perfect… until you looked a little closer. Because yes, they tagged the wrong Magnus Carlsen. Instead of the five-time world chess champion, they tagged a meme page with the same name. A small slip? Maybe. But when the world’s greatest chess player is part of your post, that’s not the move you want to blunder.
The game itself is wild. It’s in the “Head & Hand” format, and here’s how it works: NBA players team up with chess masters, where the player acts as the “Hand” (making the moves on the board), and the master is the “Head” (calling the shots). So yes, Derrick Rose is physically moving the pieces while Magnus Carlsen whispers strategy behind the scenes. It’s a knockout format, starting with a 10-minute game and no added time—if it’s tied, they jump straight into even faster, high-pressure tiebreakers.
It turns out NBA players didn’t just randomly show up to Chesstival. The Bulls legend once spilled the tea: there’s actually a secret little chess club vibe in the league. “It’s kind of a cult type thing. People whisper about it,” he told Stephen Noah. “It’s never where I say, ‘I play chess.’ It’s a thing where it’s like, ‘Hey, I play.’ ‘Oh s—, you play too?’ It’s a whisper.” During his time with the Grizzlies, he even carried two boards around, casually challenging teammates like it were part of his pregame. And that chessboard in his retirement post? Was not just a decor; it’s part of who he is and what he has brought into life—Chesstival.
Derrick Rose is turning ‘Chesstival’ into the coolest crossover in sports
Back in 2023, Rose announced Chesstival, a high-stakes chess-meets-hoops festival designed to run alongside the NBA Summer League in Las Vegas. The idea? To bring chess into the mainstream by mixing it with sports and pop culture. That first version didn’t quite happen, but it laid the groundwork for something even bigger. By 2024, Rose teamed up with Freestyle Chess, an innovative chess league co-founded by Magnus Carlsen and entrepreneur Jan Henric Buettner. Not only did Rose become an investor in their $20 million funding round, but he also became a true partner in its mission. “It’s only right that chess players get paid the right way and get seen the right way,” Rose said. “That’s one of the reasons why I have joined Freestyle Chess and Magnus Carlsen… we have the same approach and the same common goal, and that’s to put the eyes on the game.”
Now, Chesstival 2025 is finally here—and it’s going big. The one-day event takes place July 13 at the Wynn Las Vegas, just before the third leg of the 2025 Freestyle Chess Grand Slam Tour kicks off in the city. It’s being held at the elegant Lafite Ballroom and will feature NBA stars, chess grandmasters, and plenty of special guests. The event features two major competitions in one day. First, NBA stars will pair up with elite chess players for a Head & Hand team format, where the NBA player moves the pieces and the pro gives instructions, all for a $25,000 prize. Then, things heat up with an exclusive Blitz tournament, where NBA players face off against each other—trash talk included—for the title of “NBA Chess Champion” and another $25,000 in prize money. That’s $50K on the line, all going to charity, with help from partner Chess.com.
And if you’re wondering how serious Rose is about this, just hear it from him: “I really believe Chesstival is one of the biggest paradigm shifts, along with Freestyle Chess, that the chess world has ever seen, and I think they’re going to help grow the game.” What started as his personal way to “prevent dementia or Alzheimer’s” is now a full-blown cultural crossover. With NBA stars like Rajon Rondo and Tony Snell already on board, and names like Gukesh Dommaraju and Hikaru Nakamura lighting up the chess side, this isn’t just a fun side gig anymore. “Chesstival brings the energy of the court to the chessboard—redefining what a chess tournament can be,” Rose said. And honestly? He’s not wrong.
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