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Retirement appears to be treating two of the best point guards of the late 2000s and early 2010s, with former MVP Derrick Rose and two-time NBA champion Rajon Rondo enjoying their lives outside the hardwood. In fact, the two floor generals appear to be branching out into new interests — with the two dipping their toes in the sport of chess while in Las Vegas amid the 2025 NBA Summer League in Sin City.
Two of the greatest chess grandmasters of all-time, Magnus Carlsen and Hikaru Nakamura, hosted a chess competition named “Chesstival” — with Rose and Rondo being two of the highest-profile participants in the said event. The format used for the competition is “freestyle chess”, where the back rank pieces are randomly arranged. There are two rules that must be followed, however. The king must start in between the two rooks, while the two bishops must start on opposite-colored squares. Other than that, the positioning of the pieces is randomized.
Former NBA stars Derrick Rose and Rajon Rondo are competing in the “Chesstival” tournament in Las Vegas with grandmasters Magnus Carlsen and Hikaru Nakamura @chesscom pic.twitter.com/742E7oLtYb
— Ben Golliver (@BenGolliver) July 13, 2025
There is not much surprise that Rondo, who is most famous for his stints with the Boston Celtics and Los Angeles Lakers, was a participant in this event. Rondo admitted on an episode of Jeff Teague's Club 520 Podcast that he used to play chess prior to ballgames later on in his career.
Rondo is also one of the smartest NBA players of all-time, calling out plays before they happen and manipulating defenses to create openings even his teammates sometimes aren't aware of.
Meanwhile, Rose lowkey has been playing chess for a long time, although he's only been more vocal about this interest of his since he decided to retire in 2024. The former MVP with the Chicago Bulls has long been planning to join or even host a chess tournament, and now, he has gotten his wish.
Derrick Rose and Rajon Rondo enjoy life after basketball
Father Time may sap even the most legendary athletes of their speed and leaping ability, but as the old adage goes, with age comes wisdom. This appears to be the case for both Rose and Rondo, who are looking to stretch their strategic brains to the limits by continuing to expand their horizons in this post-retirement endeavor.
Both became savvy locker-room presences towards the end of their basketball careers, but now, they will put those brains of theirs to the test on the chessboard. Retirement doesn't have to be all glitz and glamour; it can also be peaceful and quiet, as both Rose and Rondo are showing.
