Chicago’s Grant Park 165 was more than just another unpredictable street race; it was a proving ground for NASCAR’s boldest new experiment: the In-Season Challenge. This head-to-head, bracket-style tournament has upended the traditional points grind, forcing drivers to focus on direct elimination battles each week. The city’s tight corners and unforgiving barriers amplified the pressure, with every lap threatening to end someone’s million-dollar dream.

As teams rolled into Chicago, all eyes were on the underdog story emerging from the bottom of the bracket, a story that had already sent shockwaves through the sport. Kaulig Racing’s Ty Dillon, the No. 32 seed and widely dismissed as a first-round casualty, had already pulled off the tournament’s biggest upset in Atlanta. Now, as the field prepared for another round of showdowns, Dillon’s run and his growing reputation for post-race trolling became the talk.

From Hamlin’s heartbreak to trolling Keselowski, Ty Dillon is on a roll

Ty Dillon’s journey through the In-Season Challenge has been nothing but incredible. Entering as the lowest seed, Dillon first stunned the garage by eliminating No. 1 seed Denny Hamlin at Atlanta’s Echo Park Speedway. A massive wreck on Lap 69 took out Hamlin and 22 other cars, while Dillon steered clear and finished eighth, his best run of the season at just the right time. Dillon wasted no time making it personal, declaring in his post-race interview, “Hey Denny fans, I knocked out your favorite driver,” a line that quickly went viral and set the tone for his bracket persona.

It was a line that Hamlin used multiple times in his career as he donned NASCAR’s black hat. Reflecting on that moment, Dillon admitted, “It was planned when I knew he was eliminated… I just wanted to lean into it a little bit. ” Even Denny Hamlin took the smack talk in lightly, telling fans on his Actions Detrimental podcast, “Give him his moment, people. He beat me,” and emphasizing that the banter is part of what the In-Season Challenge is meant to create fun rivalries and memorable moments.

In Chicago, Dillon faced RFK Racing owner/driver Brad Keselowski in another head-to-head duel. The street course’s chaos played perfectly into Dillon’s strategy: “We’re going to do our best… to put pressure on him. This is a place that, if you feel like you can pressure people, they can make mistakes”. That pressure paid off almost immediately, as Keselowski was swept into a Lap 4 crash sparked by Carson Hocevar, ending his day early. Dillon survived to finish 20th, advancing to the third round and keeping his bracket dream alive.

Ty Dillon on moving past Brad Keselowski in the In-Season Tournament, posted on X, “I knew in a basketball city, going up against Brad in a game of knockout, I was going to have a good chance.” Dillon clearly has a sharp sense of humor here, as he referenced an iconic embarrassing clip of Brad Keselowski shooting hoops!

Chicago is undoubtedly a basketball city, with the legendary 6x NBA Champion Chicago Bulls calling it their home. Fittingly, Dillon brought up a video from 15 years ago when Brad Keselowski was a part of Penske Racing in 2010. The video shows Keselowski taking part in a basketball skills challenge while wearing a shirt and jeans, and his hooping skills leave very little to be desired. From air-balling 4 free throw attempts and missing point-blank layups, it was a horror show from Brad K, and Dillon chose the perfect jibe for his In-Season Challenge rival.

Dillon also added in interviews, “I told everyone, don’t sleep on the 32. Now Brad knows how Denny felt.” Fans quickly picked up on the banter, with some joking that Dillon was living rent-free in the heads of the bracket favorites. His willingness to poke fun at his higher-seeded rivals both in interviews and online has made him a fan favorite and the bracket’s most talked-about disruptor. Dillon’s blend of opportunistic racing and sharp trolling has turned each matchup into must-watch drama, and his bracket run has become the defining storyline of this year’s In-Season Challenge.

How the head-to-head format is changing NASCAR

Dillon’s antics and upsets have rippled through the Cup garage, changing how drivers approach each race and interact with each other. Brad Keselowski, frustrated after his early Chicago exit, summed up the brutal nature of bracket racing: “Wrong spot, wrong time. The #77  [Carson Hocevar] wrecked and blocked the track. I was going to get stopped to not hit him, or if I was going to, it was going to be light, then like three cars came from behind and blasted us”.

Other drivers have acknowledged how the Challenge’s format is raising the stakes and bringing out new sides of their personalities. Denny Hamlin, after being eliminated by Dillon, said, “When drivers lean into some kind of entertainment part of our roles, it opens up doors for us, other guys to show some of our personality”. This sentiment is echoed across the paddock, as the direct elimination structure forces drivers to race aggressively and react candidly on the track and in the media.

As the In-Season Challenge heads to Sonoma, Ty Dillon’s bracket run and trolling have become the defining storyline. The Chicago round didn’t just decide who advanced; it showcased how NASCAR’s new format is amplifying rivalries, fueling fan engagement, and giving unexpected stars like Dillon a chance to shine and stir the pot. What did you think of Ty Dillon’s antics? Let us know in the comments!