It didn’t take long for Sunday’s NASCAR Chicago Street Race to produce yet another mid-season Challenge disaster, the kind that’s become all too familiar lately—just ask Brad Keselowski.
A week after Denny Hamlin’s Atlanta misfortune upended the bracket, this time it was Keselowski’s turn to watch his Challenge hopes get pancaked, courtesy of the concrete canyons of Chicago.
The chaos erupted barely four laps in, coming out of Turn 11. Carson Hocevar pinballed off both walls like a stray shopping cart in a Walmart parking lot, then spun across the straightaway, blocking much of the track. What followed was a scene ripped straight from the pages of “What Could Possibly Go Wrong?”
Keselowski, with no time to react, slammed into the mess, followed by Todd Gilliland, Austin Dillon, Will Brown, and Riley Herbst. A multi-car pileup on a narrow street course? Who could’ve seen that coming?
With the track effectively turned into a metal scrapyard and the barriers in need of serious repair, NASCAR threw the red flag. By that point, Keselowski had climbed out of his wounded No. 6 Ford and popped the hood for a quick glance—not that there was much to see other than shattered playoff hopes.
“I didn’t see it until the last second,” Keselowski admitted. “I slowed down and I actually felt I was gonna get stopped, and then I just kind of got ran over from behind. It’s just a narrow street course and sometimes there’s nowhere to go.”
It was a harsh end to what had been a promising day—and yet another headache for those trying to predict how this Challenge bracket will shake out.
Austin Dillon’s afternoon also ended in that same heap of frustration, the No. 3 Chevrolet suffering enough damage to knock him out before the race even got going properly.
“Disappointing day,” Dillon said bluntly. “We qualified 10th and thought we’d be a contender today. A car spun in front of us on the first lap and it ended our day before we could even get it started. It’s a shame, and I’m just at a loss for words at this point.”
But perhaps the most remarkable twist came not from the wreckage, but from the standings. With Keselowski’s exit, Ty Dillon—the 32nd-seed underdog who knocked out Denny Hamlin last week—advances to the next round. Yes, really.
Dillon, who most fans didn’t even pencil into their mid-season brackets, continues his Cinderella run thanks to the wreckage left behind by NASCAR’s latest street course experiment.
Another week, another bracket shattered. If this keeps up, by the time the Challenge is over, your best bet for predicting it might just be throwing darts at a wall… or bouncing them off the inside of Turn 11.
Greg was a writer for DriveTribe supporting Amazon's The Grand Tour and has been published in major publications across the country including the Los Angeles Times, the Cleveland Plain Dealer and the Atlanta Journal-Constitution. He was also a contributor to Chicken Soup for the NASCAR Soul, published in 2010, and the Christmas edition in 2016. He wrote as the NASCAR, Formula 1, Auto Reviews and National Veterans Affairs Examiner for Examiner.com and has appeared on Fox News. He holds a BS degree in communications, and a Masters degree in psychology. He is currently the weekend Motorsports Editor for Autoweek and a regular contributor to Forbes.
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