Ty Dillon’s longshot bid to win NASCAR’s inaugural In-Season Challenge remains alive and well, with two of five races in the books. The same is true for the Kaulig Racing driver’s colorful post-race soundbites.
After creating quite the buzz by mocking Denny Hamlin after Round One of the In-Season Challenge, Dillon was back at it again after Round Two this past weekend at the Chicago Street Course.
The newest butt of Dillon’s jokes? That would be Brad Keselowski, whom Dillon toppled to make it to the upcoming third round of the NASCAR In-Season Challenge bracket.
Ty Dillon Has Become A Comedian, Thanks To Some Initial Inspiration From Denny Hamlin
As the last seed in the original 32-driver In-Season Challenge bracket, Ty Dillon started out as the underdog of all underdogs. In other words, virtually no one thought he would survive even the first round.
But much to the delight of Dillon and a large chunk of NASCAR fans, he took down top-seeded Denny Hamlin in the opener. Dillon did so by finishing eighth at Atlanta while Hamlin — hampered by his involvement in a multi-car accident — finished 31st.
During his post-race TV interview, Dillon couldn’t help but revel in the reality that he’d just eliminated the three-time Daytona 500 winner as an In-Season Challenge participant.
“All you Denny fans out there: I just knocked your favorite driver out,” a grinning Dillon said.
Ty Dillon vs. The World? 😂 pic.twitter.com/4oZizO9LsG
— FOX: NASCAR (@NASCARONFOX) June 29, 2025
The playful jab was Dillon’s not-so-subtle way of needling Hamlin and his supporters by paraphrasing a line that Hamlin loves to recycle after winning races.
While Dillon’s Hamlin quip lost some of its punch after Hamlin told his podcast listeners that he actually “loved” it, Dillon was not done playfully disparaging higher-seeded drivers.
Next up: 2012 NASCAR Cup Series champion Brad Keselowski.
What Did Ty Dillon Say About Brad Keselowski After Latest In-Season Challenge Upset?
Going head-to-head with 17th-seeded Brad Keselowski in Round Two of the In-Season Challenge, Ty Dillon had little reason for optimism.
After all, Keselowski is a former Cup Series champion and 36-time Cup Series race winner. Dillon, meanwhile, has never pulled into Victory Lane in over 250 starts at NASCAR’s highest level.
Yet, just like at Atlanta, Dillon did the virtually unthinkable at the 12-turn Chicago Street Course. With a 20th-place finish, Dillon eliminated Keselowski — who limped home 37th after being caught up in an early crash triggered by Carson Hocevar.
Later, Dillon was understandably ecstatic after defeating one of NASCAR’s elite drivers for the second week in a row.
“We survived and advanced!” Dillon exclaimed during his TV interview. “This No. 10 Kaulig Racing Chevrolet team is just a tough team. We never quit. We don’t even know how to. I’m just so proud of Kaulig Racing and our No. 10 team.”
Then came the punchline.
“I knew in a basketball city (Chicago), going up against Brad in a game of knockout, I was going to have a good chance,” Dillon said, once again sporting a wide smile.
We got that reference, @tydillon. 😂 pic.twitter.com/5b8vTkazwa
— NASCAR (@NASCAR) July 7, 2025
Now, with just eight drivers still a part of the NASCAR In-Season Challenge, which pays a $1 million cash prize to win, Dillon will face eighth-seeded Alex Bowman on Sunday at Sonoma Raceway.
Will Dillon continue his bracket-busting ways this weekend? At this point, betting against him may not be the wisest idea.
“We’re just going to keep working hard, put pressure on who we’re facing next and see if we can keep it rolling,” Dillon said.