NBA players are often warned by those who came before them that their toughest decisions won’t always happen on the court. Despite the league having one of the highest average salaries among sports leagues worldwide, financial decisions can still be make-or-break for some players.
For Derrick Rose, who is starting his business career post-NBA, one of the biggest missed decisions of his life came off the court, involving fast food. Speaking on Forbes’ The Enterprise Zone, Rose shared a business opportunity he saw coming before most people did. It was the rapid expansion of the fast food chain Chick-fil-A into major northern markets.
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“I had a chance to bring Chick-fil-A to Chicago. I could’ve been the first to bring Chick-fil-A to Chicago,” Rose said.
Rose saw Chick-fil-A’s potential before Chicago did
Rose‘s connection to Chick-fil-A began during his college years at Memphis, where the brand was always embedded in Southern culture. So when Rose made the jump to the NBA after being drafted by the Chicago Bulls first overall in the 2009 Draft, there was something missing in the South Side part of the city.
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At the time, Chick-fil-A had no presence in the city and it wasn’t until 2010 that its first restaurant opened in northeastern Illinois. But the fact remained that one of Chicago’s most diverse and iconic areas had yet to see a one.
Rose first recognized the opportunity to build the first Chick-fil-A restaurant in downtown Chicago near the end of his career with the Memphis Grizzlies. Unfortunately, his financial advisor didn’t quite understand what Rose wanted to do.
“I told my financial advisor at the time that there was not one there. It was right after I got done playing, and it was one in Memphis. I was a huge Chick-fil-A fan in Memphis,” he recalled.
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“I told my advisor what was going on and what was going on down south. She ain’t understand,” he added. “A year or two years after that, Chick-fil-A was downtown Chicago, and now it’s like a lot around the block.”
The opportunity eventually went away after Chick-fil-A opened its first store on the South Side in December 2025. Since then, multiple Chick-fil-A locations have been scattered across Chicago and its surrounding areas.
The expansion validated what Rose had sensed — that downtown Chicago was ready to have one of the country’s cheapest yet high-quality fast-food chains. The missed opportunity is also a costly one for Rose, as Chick-fil-A has consistently ranked among the highest-grossing fast-food chains in the United States, despite being closed on Sundays.
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Rose is branching out his business portfolio
Despite the missed opportunity with Chick-fil-A, Rose has remained active in other business ventures since retiring from the NBA. He has actively diversified his portfolio while continuing to emphasize community-focused projects in the city he embraced.
The most notable of Rose’s business ventures has been his own flower shop in Chicago, aptly named Rose’s Flower Shop, which offers weekly flower deliveries and engages with the local community. Aside from his flower business, Rose also plans to be more involved in real estate with the 1901 Project, which is backed by an estimated $7 billion in investment and aims to transform residential and commercial spaces on the city’s West Side.
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Not to mention Rose’s various endorsement deals and other investments. He has transformed his basketball fame into an emerging business career. What’s evident in Rose’s missed and completed business ventures is that he has remained passionate about repaying the love he received from his hometown.
Related: “I was a dumb player at the time” – Derrick Rose never missed the feeling of being MVP
This story was originally published by Basketball Network on Feb 15, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.