Brandon Jennings Reveals He Had 0 Faith in Beating Derrick Rose in Chicago Despite His HS Coach’s Optimism

Brandon Jennings’ NBA career was rather underwhelming compared to his run in high school, where he was the #1 ranked prospect in his recruitment class and was touted to be a lottery pick in the 2009 NBA draft. In his junior year, he and his Oak Hill Academy Warriors, the best high school team in the country, lost only one of their 42 games. That sole loss was to Derrick Rose’s Simeon Career Academy.

Jennings knew their fate as soon as he saw it on the schedule, they had to face D-Rose in his home city of Chicago. It was definitely mission impossible from the jump despite what his coach said.

During an appearance on the All The Smoke podcast, the 35-year-old reminisced about his time at Oak Hill and claimed that transferring to the program in his junior year was one of the best decisions of his life. He then talked about the 2006-07 season, where they finished 41-1. When Matt Barnes asked if he remembered that one fated loss, Jennings said,

“That was against Derrick Rose. That was a game I was like, ‘Why would you schedule it?’ Coach [Steve] Smith being coach Smith, he was like, ‘We are going to go to Chicago and beat Derrick Rose.’ And I’m like, ‘There’s no way. There’s just no way.'”

The game, which aired on ESPN, finished in a narrow 78-75 win for Simeon Career Academy. Jennings scored 19 points in the fourth quarter, but it was wasn’t enough to overcome Rose’s masterful display.

The Chicago native finished the game with 28 points, nine assists, and eight rebounds, to lead his school to a remarkable victory against the top-ranked team in the nation. It was a devastating result for the undefeated Oak Hill and Jennings, who burst into tears on the bench during the game’s final few seconds.

The star guards would face off several more times in the NBA as opponents, but also had a brief battle as teammates.

Jennings and Rose competed for the starting job in New York

In the 2016 offseason, the Knicks traded for Rose, signed Jennings on a one-year deal and planned on letting them compete for the starting point guard role. The former Bulls star won the job, but the latter felt the competition between the two was good for his career. In an interview with the Knicks’ YouTube channel, he said,

“This camp, I had a lot to prove. I had a chip on my shoulder and I was actually going against someone (Rose) who was starting over me and actually I felt was better. So it made me go in and compete. Just wanted it more.”

Despite playing 58 games and starting 11, Jennings asked the Knicks to release him. They adhered to his wishes and he joined the Wizards as a free agent on a short-term deal.