Derrick Rose Chesstival Freestyle rousing success!
Three years ago, former NBA star Derrick Rose had an idea to host a chess tournament featuring NBA players in Las Vegas. He billed it as a “Chesstival” with a high-stakes prize fund. The idea drew similarities to Maurice Ashley’s Millionaire franchise, which had a first prize of $100,000.
Video by Freestyle Chess
Rose, who retired in 2024, was the league’s Most Valuable Player in 2011, leading the Chicago Bulls to 62 wins and dazzling crowds with his athleticism and high-flying dunks. Now, he moves on to a new chapter in his life, a challenge in the game of chess.
The tournament was delayed, but as fortune would have it, Rose was able to team with German entrepreneur Jan Henric Buettner and Freestyle Chess to host his dream tournament and attract yet another segment of chess players. Rose, who has been profiled for his “chess obsession,” was aptly paired with Magnus Carlsen for the Freestyle event.
Video by Freestyle Chess
Chess is very popular amongst NBA players, but the challenge here was that each NBA player would be teamed up with a Grandmaster to play Freestyle Chess, a form of chess where the backrow pieces are randomized.
This must’ve been a new experience for the NBA players, but it was certainly an entertaining event. Bear in mind, this was a freestyle event, which means that the athletes may have been uncomfortable adjusting to a different arrangement of pieces. There was some consolation in that the Grandmaster could assist by calling out a piece to move. This came into play when Tony Snell almost missed hanging a rook and mate.
Snell would go on to win that game against Quinten Post/Tania Sachdev and ended up in the final against NBA champion Grant Williams and the legendary Judit Polgar. This was a well-played game and appeared to be headed for a draw. Snell, who was known primarily as a three-point shooter and a defensive presence in the NBA, erred by trading minor pieces into a lost pawn ending gifting Williams/Polgar the title. Caruana could be heard telling Snell that if he just moved the knight around, “they couldn’t do anything.”
Freestyle Blitz
There was also a blitz tournament featuring NBA players, which was won by Quinten Post, who scored 4.5/5. The Dutch 7-footer gave up his only draw against Grant Williams on a stalemate while a queen up! Nevertheless, his performance was good enough to earn $25,000 for his charity, Reading Partners.
Expanding Demographics
This tournament, featuring NBA players, is the latest effort to reach an untapped market in American chess. Boston Celtics player Jaylen Brown was in the news talking about his experience as a chess enthusiast.
Years ago, there was a playoff promotion showing NBA stars playing chess. It featured players like Kobe Bryant, LeBron James, Dwight Howard, Kevin Garnett, Paul Pierce, Dwyane Wade, Chauncey Billups, Brandon Roy, and Joe Johnson. While the players were not actually playing chess, the video was impressive and perhaps shed light on the parallels between chess and basketball.
The country has been riding a wave of activity spurred by COVID-era activities. Players like Hikaru Nakamura gave chess meaningful exposure by creating interest through his online streaming platforms. Others developed streaming platforms including including NFL players like John Urschel. In fact, there was a tournament featuring NFL players back in 2022.
It has been known for a long time that entertainers, including hip-hop personalities, have had a strong following in the game of chess. The most notable names are RZA and GZA of the Wu Tang Clan, who have an entire album dedicated to chess themes.
.jpg)
What does all of this mean? This means there is an entire segment of chess enthusiasts that have not been tapped yet. There has also been the HBCU initiative to attract more Black college students to chess. There is great potential for membership growth in U.S. Chess provided there is a more creative approach taken.
There has been no strategic marketing plan to analyze how to target underserved segments. With a sport in need of sponsorship, these celebrities draw considerable attention and can certainly attract marketing dollars to chess.
It is unclear what inspired Derrick Rose to host such a tournament. Although the world’s best were competing in the main Freestyle Tour event, hopefully, there will be another Chesstival next year. Perhaps we will see a clash of NBA versus NFL players! Super Bowl Champion Jalen Hurts is reportedly an avid player. Let’s get it on!
Freestyle Grand Slam Tour: https://www.freestyle-chess.com/
Chess.com (Levin): https://www.chess.com/news/view/williams-post-win-2025-chesstival
Derrick Rose Highlights