Chess as a Metaphor for Life

Rose’s fascination with chess often surfaces in how he describes his own journey. In interviews he has cited legendary world champion Bobby Fischer as an obsessive figure he admires, hinting at the kind of dedication he sees in both great athletes and great chess players. He explained that in chess, a comeback with fewer pieces requires “strategy, heart and skill”, implying that he reinvented his game with those same qualities. This vivid analogy – delivered with emotion after an NBA comeback – shows how deeply chess has influenced Rose’s perspective. Clearly, Rose doesn’t just play chess for fun; he often thinks in chess terms when evaluating strategy, teamwork, and personal growth.

From NBA to Freestyle Chess: Launching Chesstival

Rose’s engagement with chess evolved from a private hobby into a public venture when he decided to bring chess to a broader audience. In 2023, he announced the creation of Chesstival, a high-stakes chess festival timed alongside the NBA Summer League in Las Vegas. The concept was to merge chess with sports and pop culture, bringing new eyes to the game. Although the 2023 Chesstival event didn’t ultimately take place, it set the stage for Rose’s next chess endeavor: partnering with an innovative new chess enterprise.

In 2024, Derrick Rose joined forces with Freestyle Chess, an upstart chess organization co-founded by former chess World Champion Magnus Carlsen and entrepreneur Jan Henric Buettner. Rose became not only an investor in the league’s $20 million venture funding round, but also an active proponent of its vision. He saw Freestyle Chess as a chance to shake up the chess world.

“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,” Rose remarked, emphasizing his confidence in the project. In Rose’s view, traditional chess tournaments needed fresh energy and more reward for players’ dedication. “It’s only right that chess players get paid the right way and get seen the right way,” he explained in one interview, “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”.

Chesstival 2025 – NBA Stars Meet Chess Champions

With Rose on board, Freestyle Chess folded his earlier idea into the Grand Slam series. The marquee result is Chesstival 2025, an unprecedented pro-am chess showcase co-organized by Rose and the Freestyle Chess team. Slated for July 13, 2025 at the Wynn in Las Vegas, Chesstival is designed as a crossover event where Rose’s two worlds collide.

The format features current and former NBA players paired with elite chess grandmasters and collaborating. In addition, the NBA players will square off against each other in a blitz chess tournament to crown an “NBA Chess Champion,” trash-talking and competitive fire included.

Rose’s hope is that “Chesstival brings the energy of the court to the chessboard – redefining what a chess tournament can be”. The one-day festival boasts $50,000 in charity prize funds (courtesy of a partnership with Chess.com) and has attracted big names: apart from Rose himself, other NBA participants announced include Rajon Rondo, Tony Snell and many more. For the first time, a chess event will feature NBA personalities not just as spectators but as competitors, an idea born from Rose’s unique position in both sports.

“From Englewood to owning a chess league and a chess paradigm called Chesstival,” Rose proudly wrote, reflecting on how far he had come from Chicago’s South Side to this new role. By late 2024 when he parted ways with the Memphis Grizzlies, Rose was already referring to himself as “Commissioner Pooh” (after his childhood nickname) of his chess league, embracing the leadership role in this chess venture.

Commissioner Pooh El Dini Rose

As Derrick Rose delves deeper into the chess world, he’s developed a fun chess persona and has actively promoted the game on social media. In chess circles, Rose has adopted the tongue-in-cheek moniker “El Dini,” a play on the famous chess engine Houdini (and perhaps a nod to his own magician-like creativity on the court). Freestyle Chess’s social media accounts have leaned into this nickname: one promotional reel quipped: “Some use Stockfish, some Houdini, former NBA MVP Derrick Rose uses the Dini”. Rose himself signed an Instagram post as “Commissioner Pooh El Dini Rose”, cementing the alter ego.

Fans embrace his chess references. A clip of Rose playing chess on his phone during a Drake concert (see clip below) made the rounds online. On his personal accounts, Rose periodically shares chess puzzles, quotes, or stories, blending them with motivational messages. In one Instagram story in 2025, he mused about teamwork and honesty, implicitly comparing a strong support system to a “great team” in chess where every piece matters. Such posts show Rose evangelizing the lessons and culture of chess to his millions of followers.

Ready for the spotlight

Rose’s public embrace of chess has drawn positive attention from both sports and chess media. A GQ feature in 2024 discussed the growing “hidden” community of chess enthusiasts in the NBA – something Rose himself noted, calling chess popularity among players “kind of a cult… more of a hidden type of community”. By stepping into the spotlight as a chess ambassador, Rose has helped bring that community into the open. He stands as perhaps the most prominent NBA player to champion chess so directly, leveraging his fame to bridge the two worlds.

“We’re helping show that I’m more than a hooper,” Rose wrote in gratitude to his chess partners. Indeed, through Chesstival and Freestyle Chess, Derrick Rose has transformed from a basketball icon into an influential chess promoter. He envisions a future where chess is treated like a major sport – with energetic live events, celebrity appeal, and financial support for its players – and he’s actively working to make that vision a reality. As Rose says, “It’s time for a new paradigm!”, and he’s betting that chess is ready for its moment in the spotlight.