Every NBA player arrives at the professional stage from a unique background. For some, the road is paved with support and guidance from both parents, providing a foundation of stability that eases their path to success. For others, their journey is defined by hardships and responsibilities far beyond their years.
Brandon Jennings is a poignant example of the latter. So much so that Jennings recently revealed how he held deep resentment for players like Jrue Holiday and DeMar DeRozan while growing up, simply because of the privilege of being in two-parent households, a luxury that Jennings never experienced.
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Jennings on envying Holiday and DeRozan
The trajectory of Brandon’s life changed when he was just three years old. His father initially separated himself from his mother, and a few years later, took his own life. Unsurprisingly, this left Jennings’ family not only grieving but also struggling financially. As a result, by the age of 11, the former Milwaukee Bucks point guard began contributing to household expenses, handing his mother money for rent.
Put simply, at an age when most children are shielded from life’s difficulties and made to focus on their craft, Jennings was forced to bear responsibilities that accelerated his maturity.
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In a recent interview with Tee Morant, Jennings shared the depth of his personal struggles, admitting to bluntly envying his peers who were protected by the steady presence of both their parents. Beyond the financial support, Jennings recognized the emotional comfort that comes from having two pillars of guidance — a comfort he never experienced, just dreamed of.
“The reason why I wanted to be so much better than them is that I envied them because they had both parents. I’m coming to the gym at a young age, and I’m seeing Jrue Holiday with both his parents, Demar DeRozan, Larry Drew and Malcolm Lee, and it made me really envy them,” the shifty lefty said. “I knew that at the end of the day, they’re going home to both parents with the tools and everything, and I got to figure out where’s my next meal or I got to play in this AAU tournament.”
Jennings did his best to carve out a career in the NBA
When looking at his career trajectory, Jennings’ accomplishments may appear modest compared to the league’s brightest stars. Across nine seasons, he averaged double-digit scoring in six. Moreover, he did not earn an All-NBA or All-Star selection, nor did he become the defining face of a franchise. Ultimately, by the age of 29, his NBA career had concluded.
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However, to assess his journey purely by accolades would be incomplete. During those nine seasons, Jennings earned an estimated $40.3 million in career contracts. For someone who once worked as a child to support his mother, this achievement stands as a powerful testament to resilience. Although Jennings’ prime years did not cement him among the elite players of his era, his story is one of profound triumph.
So, it does seem safe to state that success in Jennings’ case can never be measured by achievements; instead, one needs to appreciate the perseverance he showed to hold himself together in the NBA for nearly a decade.
This story was originally reported by Basketball Network on Aug 25, 2025, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.