Growing up in one of the roughest neighborhoods of Chicago was not easy for Derrick Rose and his family. Pooh did what he could to survive and bring his family out of that situation. Basketball was the way out. But while he was a young kid in the Chicago Southside, he wanted to help his family with just a few extra bucks. Yet to keep his pro sports future secure, he had to keep it safe. He opened up about his youth as a ‘hustler’ to Zach Randolph and Tony Allen.

Allen, a fellow Chicago native, related to D-Rose’s background when he asked how he navigated the tough situation he grew up in. In those times he relied on his brothers to stay focused. When he worked out too late in the gym, his mother picked him up so young Derrick was not walking in unsafe parts by himself. However, Rose ventured into those areas for extra cash.

“I learned how to shoot die in that park…” Rose told the hosts and narrated how that got him into trouble. “One of the scariest days ever, because my brother caught me, you know what I’m saying.” 

He didn’t name which of his older brothers found him but gave a hint. “At the time I really didn’t care… because that n—- was selling dr-gs anyway.” It could be Alan Rose who was arrested in 2002 on dr-g related charges.

Rose was picked first overall by his hometown team. But years before that, he was defiant against his brother. “I’m like, this is the cleanest way I can hustle right now.” Other than dice, Rose also said he was selling the shoes he was given among other side hustles. And it was the youngest of the Rose family’s way of helping them out.

Derrick Rose did everything for his family

For his entire public life, Derrick Rose has been vocal about his mission to get his family out of the Englewood neighborhood. Earning millions in the NBA did that, but he was trying long before he got to the league.

Being caught by his brother was not going to stop young Derrick Rose. He told his brother that he’d have to “deal with it” because he was not involved in substances and violence. “[I’m] just trying to find ways to go back to my mom like, ‘Hey, here you go 20.'” 

He was thrifty about it too. He’d give his mom only half of the earnings to invest the rest back into the hustle and would occasionally take the money he gave to her too.

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This wouldn’t be contentious for the Rose brothers. Dwayne, Reggie, Allan, and Derrick always had each other’s backs. In a documentary, Reggie said that Alan’s history nearly derailed his NBA career but Pooh told the Bulls not to pick him if they weren’t going to accept his brother.

“The good, the bad, the ugly, me and my family, my brothers, know that no matter what, we got each other’s back,” Rose said in 2019 and still sticks by it.