Brad Keselowski’s run-ins with the Chicago Street Race have been a wild ride of grit and bad breaks. In 2023’s inaugural Grant Park 220, Keselowski rolled off 20th in his No. 6 RFK Racing Ford and finished a frustrating 24th. Heavy rain, tight corners, and a flurry of cautions made the race a chaotic mess, and Keselowski never found his groove. “It was a chaotic afternoon,” his team noted, a polite way of saying the street course chewed up their strategy and spit it out.  But in 2024’s Grant Park 165, Keselowski showed some fight.

He qualified 10th, but an unapproved pre-race tweak forced him to the back of the pack. Then rain cut the race to just 58 laps. Still, he clawed his way to 18th, a testament to RFK’s resilience and his growing knack for navigating Chicago’s tricky layout. But 2025? That proved to be a whole different beast. A freak pile-up on Lap 4 snuffed out any hope of a breakthrough, leaving Keselowski shaking his head at his rotten luck.

Brad Keselowski suffers yet again

The chaos started when Carson Hocevar clipped Turn 11’s inside curve, bouncing off the outside wall and twisting back across the track. Austin Dillon, Daniel Suárez, Todd Gilliland, Will Brown, and Riley Herbst got caught in the seven-car mess, with Keselowski’s No. 6 taking a brutal hit straight into the back bumper of Dillon that snapped his left-front suspension. A red flag halted the race to untangle the wreckage, but for Keselowski, it was game over. His spotter’s heads-up couldn’t save him, as there was simply no escape.

After the Lap 4 disaster at the 2025 Grant Park 165, Brad Keselowski was honest: “Wrong spot, wrong time,” Keselowski said, a four-word admission that sums up his season so far with RFK Racing. The veteran 2012 Cup Series Champion now sits 28th on the playoff points grid, 136 points away from the cut line as his hopes dwindle. This wreck also marked his 5th DNF of the season!

Keselowski continued, explaining what happened in that multi-car wreck, “The 77 [Carson Hocevar] wrecked and blocked the track and I was gonna get stopped, not to hit him or if I was going to be very light, then like three cars came in from behind and blasted us, so it broke the left front suspension of the car. It’s a shame we never got a chance to show what we had, thought we were pretty good, but that’s just how it goes.”

Another point to note is that the spotter’s visibility was a key talking point heading into the races. NASCAR insiders and drivers alike noted that the change in the spotter’s stand, along with blind spots, would make this race chaotic to call. However, Keselowski admitted that his spotter, TJ Majors, did a good job. He added, “Actually, my spotter did tell me he did a good job; he called out the wreck, but there was nowhere to go.”

That pile-up was a gut punch. Keselowski and RFK Racing came in hot off a strong second-place run in Atlanta, feeling good about their setup. But Chicago’s tight streets and Hocevar’s Turn 11 mishap put them in the wrong place at the worst moment. But for now, Brad Keselowski has to balance his misery as a driver with his ambitions as a team owner, because, off the track, Keselowski’s got bigger fish to fry.

RFK Racing’s leadership hunt

RFK Racing’s president, Steve Newmark, is stepping down after 15 years to join UNC athletics as Executive Associate Athletic Director in Chapel Hill, starting August 15. Newmark’s exit leaves a big hole for a team that’s been inconsistent in 2025. However, ever since the All-Star race, Keselowski, Chris Buescher, and Ryan Preece have been bringing the heat, with Keselowski’s Atlanta runner-up finish showing RFK’s playoff potential.

However, they’re on the hunt for a new leader to keep the momentum rolling. Brad Keselowski stayed cool about it, telling the media, “We are still kind of working through, we are not in a rush, we’re in such a great spot. We all have our major contracts locked up with the drivers, crew chiefs, and most of our people… We feel really good about taking our time and kind of seeing what comes to us.”

RFK’s got stability key contracts are locked in, and the team’s in a strong place with Buescher, Keselowski, and Preece all chasing wins to secure playoff spots. The Grant Park 165 was a bust, but with another road course coming up in Sonoma, Keselowski’s banking on RFK’s depth to carry them forward. They’re not rushing the leadership search, confident they’ll find the right fit to keep pushing for that checkered flag.