Money will always matter in the NBA. Any player who claims otherwise either has enough tucked away or is lying through their teeth. One player who made enough in his brief nine-year NBA career was Brandon Jennings .
An explosive 6'1" guard who the Milwaukee Bucks picked 10th in the first round of the 2009 NBA Draft, Jennings showed a lot of potential in his first four seasons, averaging 17.0 points and even scoring a whopping 55 points in a single game during his rookie year. Impressed by his scoring chops and fearlessness, the Bucks tried to make Brandon an offer to become one of the Bucks' cornerstones.
According to Jennings, that's where things got muddy: he claimed his agent at the time, Bill Duffy, didn't clue him in, which eventually led to him being traded away from the Bucks and playing for four different teams over the next five years.
As someone who had to scratch and claw his way to earn a spot in the NBA, Jennings was looking to get the bag and secure financial stability. He believed that moment had finally arrived after playing well in his first four seasons in Milwaukee. Unfortunately for the lefty guard, Duffy received a substantial offer from the Bucks but didn't relay it to his client.
"That's the reason why I left my agent, Bill Duffy. At the time, he didn't tell me Milwaukee had offered me a four-year, $40 million contract. He never told me. So at the beginning of that year, Milwaukee offered me four years, $40 million. My agent didn't tell me," Jennings recalled .
"What happened was, John Hammond, the GM at the time, mentioned it to my Under Armour rep. He said, 'Can you believe this kid didn't take four years, $40 million?'" he narrated. "I was like, 'What?' I had no idea they had even made that offer."
Unbeknownst to him, Duffy had been angling for Jennings to receive a max offer from the Bucks. What made the situation worse and especially painful was the fact that his own mother knew about these developments yet never told him about them.
"My agent came back and said, 'Yeah, I don't think four years, $40 million is it. We should go for the max.' My mom and my agent were both pushing for the max," Jennings remembered. "It kind of messed up my relationship with my mom, too, because it felt like they were doing things behind my back, and I didn't even know. By the time I found out, it was too late to sign."
In July 2013, Jennings was traded to the Detroit Pistons and received a three-year deal worth more than $25 million. However, the experience undoubtedly left a bitter taste in his mouth, especially since he never wanted to leave Milwaukee in the first place.
"That whole experience helped me and hurt me at the same time. But that's just part of the game," he stressed.
Jennings entered the NBA at age 20. So, it was completely understandable that he didn't know much about the business. Unfortunately, those whom Brandon trusted to guide him through the entire process ended up keeping him in the dark, leaving him with a pain that not even a hefty contract could fix.
This story was originally published by Basketball Network on Aug 5, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.
