In 2008, Brandon Jennings made headlines. He was one of the first American players to skip college and play professionally for the Lottomatica Roma in Italy. The gamble paid off when Milwaukee drafted him 10th overall in 2009. He immediately proved his worth by dropping 55 points in just his seventh NBA game. For a few exciting years, Jennings looked like the future of the point guard position. But everything changed in 2015 when he suffered a devastating Achilles injury. Though he tried to fight back through stints with several teams. Detroit, New York, China, and the G League, and even overseas. But he was never the same player again.

The once-promising star was forced to retire in 2018 at just 29 years old, a heartbreakingly early end to what should have been a spectacular career. However, Brandon Jennings managed to keep his spirit intact. Even though he faced personal and financial struggles post-retirement. Without wasting any time, he founded TUFF CROWD in 2018 in Woodland Hills, California. It’s a clothing brand that reflects Jennings’ journey.

In 2023, TUFF CROWD collaborated with Stephen Curry’s Curry Brand. This partnership also led to the refurbishment of Rowley Park Gym in Gardena, California, Jennings’ childhood court, highlighting their commitment to community engagement. However, he wasn’t alone through the brand’s launch and later journey. Brandon Jennings has built strong relationships with several A-listers who helped him throughout. On VladTV’s Youtube channel, he recently acknowledged these people, and among these people was a name no one expected!

“Um Khloe Kardashian, you know I was around them early and she was the one that helped me with my bio and tell me to go out there and tell everybody you know this is your brand.” This one was especially striking because of their complicated history. Brandon Jennings and Khloe Kardashian reportedly dated for a brief period of time. The two were having a dinner date on a weekend at Nobu in Malibu.  Although they were with some friends including Khloe’s close friend Malika Haqq, an eyewitness told Media Takeout that Khloe and Brandon looked like more than just friends, reports aceshowbiz.com.

Brandon Jennings was also the common friend that set up Khloe Kardashian with Tristan Thompson in 2016. Even though Tristan Thompson cheated on Khloe Kardashian later, the reality star didn’t seem to hold it against the cupid who set them up. This shows sheer maturity on both of their parts and proves that some bonds have the power to withstand complicated moments.

Brandon Jennings’ bittersweet truth

Brandon Jennings’ career trajectory changed forever on January 24, 2015, when he collapsed to the floor with a torn Achilles. The injury didn’t just derail his season, it altered the course of his NBA journey. Jennings opened up on VladTV “I would’ve been an All-Star for sure if I didn’t tear my Achilles,” there was a lingering frustration evident in his voice. At the time of the injury, he was in peak form, averaging 20.9 points and 7.9 assists that month for a Pistons team that had won 12 of their last 15 games.

The six-month rehab that followed became a battle not just for his body, but for his basketball identity. “I feel like with the injury, that’s when the chaos started happening outside of my career,” he admitted, acknowledging how the setback triggered professional instability. After being traded from Detroit to Orlando, he had hopes of a one-year deal in New York. “I think after the Knicks, I knew like my time was done.” Brandon Jennings confessed about that disappointing season where the anticipated superteam with Melo and D-Rose failed to prove it.

His voice carried the weight of unfulfilled potential as he described the gradual realization that his NBA window was closing. “Once I got to Wizards, I was just holding on.” The final chapters saw him return briefly to Milwaukee before finishing his professional career overseas. Yet amidst the career turbulence, Jennings found unexpected joy. “That was the best experience of my life,” he said of his time playing in China. “But the only good thing that came out of it? I still got to play with my dream team, the Knicks.” That was after all, one silver lining he will always cherish.