There’s beauty in connecting the dots of a journey and returning home to where it all began. For Derrick Rose, a Chicago native, the tough love of his city shaped him into one of the most generational talents basketball had ever seen.

From his days as a highly recruited player at Simeon Career Academy in Chicago to leading the University of Memphis to an NCAA record for wins (38–2) in a single season under coach John Calipari, Rose’s rise was electrifying. Drafted first overall by his hometown Chicago Bulls in the 2008 NBA Draft, he was named NBA Rookie of the Year in 2009 and became the youngest MVP in league history in 2011 at just 22 years old. Rose spent eight memorable seasons with the Bulls, etching his name into Chicago’s sports history.

He went on to spend seven additional years in the NBA, playing for five different franchises. Yet, as the saying goes, there's no place like home. Derrick Rose remained Chicago's beloved son.

Yet, focusing solely on Rose’s on-court greatness would miss the heart of his story. Hollywood couldn’t do justice to his journey—it’s too raw, too real. Like his name, Derrick Rose has bloomed against the odds, rising from the concrete. Now, at 36, his story offers timeless lessons on leadership, grit, and the art of giving back.

Last week was special—not just for Rose and his family but for the Chicago Bulls organization and the city itself. Amid the Chicago windy winter, Rose returned to the city that raised him, and Chicago turned out for him. He curated a one-day floral pop-up, hosted a basketball court activation at Clybourn Park, and learned Saturday morning that the Chicago Bulls plan to retire his No. 1 jersey next season. This honor places him among franchise legends Jerry Sloan, Bob Love, Scottie Pippen and Michael Jordan.

Hours later, the Bulls hosted Rose, his family and former teammates at the United Center during their game against the New York Knicks. Both teams wore shirts honoring him, and the Derrick Rose Atrium Experience debuted, showcasing memorabilia from his remarkable career.

This weekend was more than a celebration of Derrick Rose—it was a masterclass in leadership and life. Here are a few lessons his journey and this special experience offers us:

Authentic leadership is about being real, not perfect. It’s about standing in truth—the good, the bad, the messy, the ugly—and finding grace, beauty and perspective to share our light during and after the storm.

Great leaders connect the past with the present to shape the future, never losing sight of where they came from because it’s the essence of who they are. Derrick Rose’s journey reminds us to find moments to return and reconnect with our roots—physically, mentally, spiritually or emotionally.

Rose is proud of his city, and his city is proud of him. His journey inspires us to bloom where we’re planted, rising from our own concrete and leaving behind roses—roses from the heart, filled with love, wisdom, courage, truth and a path for others to follow and be inspired by.

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