Imagine landing a multimillion-dollar NBA contract as a young athlete from a humble background. What do you do next? For many, like Dwyane Wade, who left college to join the NBA at 21, the immediate move is to take care of family and change their circumstances. But not everyone handles it well. The same fate would have followed Charles Barkley if not Grant Hill’s mother had sound advice on this, advice that someone like Brandon Jennings could have used to avoid the pitfalls he faced in his career.

Jennings recently opened up about his struggles on Above The Rim with DH 12, reflecting on how his family and friends pushed him to a breaking point. When asked how NBA money affected his life, Jennings admitted, “I had to walk away from the game too because of family and friends… it got too much about money.” For Jennings, basketball was his escape—his therapy. But when the game became a job, he noticed people viewing him as a walking ATM. “It kind of gets depressing,” he said, clearly worn down by the weight of expectations.

Jennings didn’t hold back on the toll it took, saying, “No matter who you are, you don’t want to be looked at as a cash cow.” His advice to avoid this trap? “Stay spiritual… keep the right people around you.”

Jennings earned over $40 million in his nine-year NBA career, but his net worth today is estimated at just $16 million. It seems if Jennings had someone like Grant Hill’s mother in his life, things could be different. Why? Speaking on Club Shay Shay, Chuck recollected during the 1996 Olympics Grant Hill’s parents visiting them. As per Barkley, they wanted to leave for work after a couple of games. And he tried convincing them they didn’t have to since Grant had signed a $100 million contract. But Hill’s mom advised him, “Do not start taking care of family and friends.”

Chuck further explained her advice, mentioning that she told him once he undertakes financial care of people, it becomes a never-ending cycle. And the first time he will say no to someone, that relationship will be over. Later, Barkley himself noticed it: “People I had been giving money to, the first time I told them, no, they like, no, no, we’re not friends anymore. That was a tough and painful lesson,” he said on the podcast.

Chuck’s charity ventures and Jennings’ regret

However, because of this advice, Charles Barkley hasn’t shied away from helping others financially. Since 1995, the Charles Barkley Foundation has supported various causes. In 2022, Barkley pledged to donate $1 million to Spelman College, influenced by the impact it had on his business partner’s daughter. Barkley shared his motivation, stating, “John has been a great mentor… and with his daughter doing great things at Spelman, I told him, ‘Why not there?’” Beyond Spelman, Barkley’s generosity also extends to a $5 million donation for students of color at his alma mater, Auburn University.

For Brandon Jennings, though, financial management has been a tough road. On the Gil’s Arena podcast, he admitted that one of his biggest regrets was spending his first NBA paycheck on buying his mom a house. While it was a well-intentioned gesture, Jennings now wishes he had thought more about his own future.

“That doesn’t mean I don’t love my mom,” Jennings explained. “But it’s like, woah, you can get hurt next year… and I made people comfortable too early.” The former NBA star further reflected on how not having a father figure played into his choices, noting, “I’m also the reason why I’m here.”