It's one thing that the NBA world didn't get to see Derrick Rose play at his highest level for a long time. But what makes his injury-plagued career even harder to come to terms with is how widely regarded he is as one of the most genuine and well-liked players of his generation.
Richard Hamilton once shared a story about his former Chicago Bulls teammate that only reinforces the notion.
Appearing on the "All The Smoke" podcast in 2020, Hamilton recalled when the 2011 MVP landed a lifetime deal with Adidas that could potentially pay him $250 million around the same time he inked a lucrative extension with the Bulls. Despite all that money, Rose was unsure how to spend it.
"He just signed a $250 million deal with Adidas, another $150 million from the Bulls. He got $400 million at 23 years old. And I looked at him in the locker room and said, 'Bro, do you know you just signed for $400 million?' And he like, 'What you mean?' He don't even know the impact of that," Hamilton said of Rose
"I told his brother, Reggie, after the game, 'Yo, congratulations.' He was like, 'Rip, my brother don't even know what just happened. He called me and asked me the other day is it okay if he buys a Bentley.' I said, 'What?' How many dude do you know that just made $400 million that will call his big bro and like, 'Yo, is it cool for me to buy a Bentley?' That just tells you what type of dude he is," Rip continued.
Crunching the numbers
Hamilton may have embellished his story a bit. Or maybe he overestimated the value of Rose's agreement with Adidas and his contract extension with the Bulls in 2011.
The former first overall pick actually inked a five-year, $94.8 million deal with Chicago, while reports at the time indicated his contract with Adidas was worth a little less than $200 million. So, Rip was off by $100 million. Well, Rose could still have bought multiple units of Bentley with the money he was about to earn if he had wanted to. That would have run contrary to his humble nature, though.
Interestingly, Rose wasn't even supposed to be eligible for such a sizeable extension with the franchise from the Windy City.
However, the 2011 NBA Collective Bargaining Agreement included the " Derrick Rose Rule," which allowed players coming off their rookie contracts to sign for 30 percent of the salary cap as long as they had been voted to start in two All-Star Games, named to an All-NBA Team twice, or win MVP. The clause was named after him because he was the only player to have qualified for such a contract at the time.
When asked about the rule in late 2024, the Chicago native didn't even talk about his personal gain. Instead, he viewed it as a way for his peers to get paid . Perhaps that ties into his selfless characteristic, which impressed Hamilton and many others in the NBA.
From superstar to role player
It's a shame Rose's prime lasted for only a few years. The silver lining was that his fans still got to see him suit up until 2024, even if most of those seasons saw him battle myriad injuries and go from a superstar to a journeyman.
We can only imagine how many hearts the University of Memphis product could have broken had the injury curse bypassed him. As Hamilton also said, Rose was probably the most talented player he had ever been teammates with. That's saying a lot, considering Rip played alongside the likes of Chauncey Billups , Rasheed Wallace, Ben Wallace and a Washington Wizards-era Michael Jordan.
Still, Rose was more than fortunate to have played as long as he did. Other would-be superstars didn't have that privilege because of the impact of their injuries on their bodies. Hopefully, he is reaping the fruits of his labor — maybe a couple more Bentleys? — now that he is retired.
This story was originally published by Basketball Network on May 2, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.

