Derrick Rose never planned on becoming a chess player. As a kid in Englewood, his hands were more familiar with dice than with rooks and pawns. The streets taught him survival, quick decision-making, and the art of calculated risks. The skills that later shaped his game on the court. But now, years later, the former MVP is shifting gears. In a recent Instagram post, Rose reflected on his journey from rolling dice in Chicago to moving chess pieces in Germany. A poetic metaphor? Maybe. But for Rose, it’s proof that life, much like chess, is about making the right moves at the right time

In a recent Instagram story, Rose shared a glimpse into this mindset. He posted a photo of cards, dice, and chess pieces, accompanied by a caption that read, “I started with grabbing those dice first, but now I’m pushing those chess pieces. From Englewood to Germany.” The post was a nostalgic trip down memory lane, a reminder of where he came from and how far he’s come. 

 Rose has carried his skills worldwide, from playing dice in the streets of Englewood to maybe checkmating chess greats in Europe. More importantly, though, he has brought his tale with him. He has come to represent hope by demonstrating that you can always change your course, regardless of where you begin. Starting in Germany!

From gambling on the street to chasing checkmates: Derrick Roses’ journey

But here’s where things get interesting: Derrick Rose has long been a chess aficionado. He has often talked about how the game sharpened his mental approach and changed his perspectives toward life. In January, during an interview with SLAM, he said, “I’ve also been playing a lot of chess and hopefully somewhere down the line within the next couple of weeks, I’ll ink a chess deal [and] you’ll be hearing about it pretty soon” 

The deal in question is his very own, Chesstival.  This event is set to take place at Resorts World in Las Vegas during the NBA Summer League. While not much has been made public about the event, the website notes that it’ll include ” top athletes, musicians, and other notable chess aficionados.” Your guess is as good as mine when you think of the potential participants. But the event is truly groundbreaking once you consider it is D-Rose who is spearheading it!

Jan 4, 2025; Chicago, Illinois, USA; Chicago Bulls and New York Knicks former player Derrick Rose speaks during a press conference answers questions. Rose will be honored at halftime in a game between the Chicago Bulls and the New York Knicks at United Center. Mandatory Credit: David Banks-Imagn ImagesThe buzz is certainly building as fans have begun speculating who the potential participants might be. His not-so-cryptic story on Instagram didn’t help either. But one thing’s for sure: Rose is stepping into unchartered territory. But he’s done that before when he was drafted No. 1 overall by the Bulls.

In chess, just like in life, every move matters. Derrick Rose understands that better than most. He has experienced both checkmates and comeback victories, on and off the court. Whether he sits across from a grandmaster or invites Travis Scott for a bout of the “royal game” remains to be seen. But his approach to life remains the same: keep moving forward, one calculated step at a time