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Did You Notice?: The Last Million-Dollar Moment of the NASCAR Dillon Brothers?

Did You Notice? … Ty Dillon is in position to win $1 million this Sunday (July 27) as the winner of the NASCAR Cup Series In-Season Challenge.

All he’ll need to do is finish ahead of Ty Gibbs in the Brickyard 400 and he’ll get the money, even if Dillon runs 38th and Gibbs winds up 39th.

That 38th-place finish could wind up the biggest accomplishment of Dillon’s career. At 33 years old?

It could also be his last.

So much was expected of Ty and older brother Austin Dillon when they entered the NASCAR scene over a decade ago. It’s hard to believe it’s been 12 years since the Dillon brothers enjoyed the peak of their stock car success.

Austin, just two years after winning the NASCAR Craftsman Truck Series championship, won the NASCAR Xfinity Series title despite not winning a single race (he was able to win one moonlighting in the Truck Series that year). Ty was excelling over in Trucks, scoring two victories on intermediate ovals (Kentucky Speedway, Texas Motor Speedway) while finishing runner-up to Matt Crafton for the season championship.

It’s hard to believe now, considering how Ty’s career has gone, but he topped that series in laps led (501) for the season. Both drivers were rewarded for their hard work; Austin moved to Cup, returning Dale Earnhardt’s iconic No. 3 to Cup Series competition while Ty stepped into Xfinity. The future of Richard Childress Racing was bright, with his grandsons prepared to take the mantle and propel the company forward after the departure of Kevin Harvick.

There’s just one small problem: it never happened.

The two Dillon brothers have grown up to combine for 695 Cup starts. Heading into this weekend’s Brickyard 400, they have totaled just 515 laps led in their entire Cup careers — just barely more than the 501 Ty racked up that fateful season over in the Truck Series.

Both men have struggled under the weight of lofty expectations. As month-long slumps turned into years, they’ve become the poster children for family nepotism in the sport: a famous connection keeping them in rides other people would have lost long ago.

At least Austin has a Daytona 500 win to his credit: last-lap contact with Aric Almirola propelled him to the front of the field in 2018. That’s not the only victory that’s spurred controversy. A triumph at Richmond Raceway last August was achieved in overtime by knocking first Joey Logano, then Denny Hamlin out of the way en route to the finish line.

Drivers reacted viciously to the move — a shocking upset turned simply upsetting for all involved. Dillon entered the weekend hundreds of points behind the cut line for the playoffs and needed a victory to qualify. Ultimately, NASCAR let him keep the win but removed the postseason eligibility that came with it.

His reputation? It hasn’t been the same. Almost a year later, Dillon has yet to score another Cup Series finish better than seventh.

At least the elder Dillon has some Cup victories to speak of: five, to be exact. Ty has yet to reach five career top-five finishes despite nearly a decade racing at the sport’s highest level.

Part of that was Ty never getting an opportunity behind the wheel of a RCR Chevrolet. Instead, upon his ascension to Cup, Dillon was first shipped to Germain Racing, a satellite operation that was one of the sport’s few remaining single-car teams. The resources appeared a step below the main team, which itself was struggling to remain a borderline playoff contender.

The Germain/Ty Dillon partnership showed promise in year one, raising the average finish of the car to 20.7 from 25.6 a year prior. But by the end of 2018, that number had fallen back to 24.1, right in the range of where previous driver Casey Mears had kept it most of the decade.

By 2021, GEICO had bolted, Dillon was out of a full-time ride and struggling with mental health. In an emotional podcast in March of that year, he indicated his time driving in NASCAR might be over, saying simply, “I quit today.”

Frontstretch was one of many who chronicled his mental health journey back, wrapping up that fall with a full-time deal to return to the Cup Series with Petty GMS Motorsports, which has since gone on to become Legacy Motor Club. As Dillon told our Daniel McFadin after a year spent away from failed expectations, “Now, my motivation is just pure love of the sport.”

But a more upbeat Dillon, at peace with the prospect of never having his career quite pan out like it should, hasn’t turned into better results. His current gig at Kaulig Racing marks the fourth different team he’s driven for the past four seasons: Petty GMS, Spire Motorsports, Rackley WAR in Trucks and Kaulig. He has yet to produce a single top-five finish among them.

Dillon, in fact, has come to the table for this million-dollar finale posting no finish better than eighth during the In-Season Challenge. An eighth-place finish at Atlanta Motor Speedway, his best result in nearly five years, was enough to knock out Hamlin as the 32nd and final Cinderella seed. Runs of 20th, 17th and 20th ever since would be average on a normal Sunday; they’ve just been enough in this head-to-head format where a bad day from your competitor sends you through.

Now, Dillon faces a miraculous ending: the one (and perhaps the only?) In-Season Challenge Winner in the sport’s history. It’s also a near full-circle moment: Dillon’s only Xfinity Series win came at Indianapolis Motor Speedway back in 2014, easily the most prestigious victory in his NASCAR career.

The million dollars will be quite an achievement. It also won’t obscure an awkward reality of another tough year. Dillon sits 30th in the standings, an almost-impossible 163 points behind the cut line with five races left. He’s got 83 fewer points than Kaulig teammate AJ Allmendinger and has led only eight laps on the year.

Only 16 points above him sits his brother, Austin, 28th in the standings with the same number of laps led (eight). After a third straight top 10 at Texas Motor Speedway in May — his only ones of the year — the elder Dillon’s gone nearly three months without one. Meanwhile, RCR prospects Jesse Love and Austin Hill are busy winning races and challenging for the NXS title; Hill himself scored the first top 10 of his Cup career at Chicago’s street course earlier this month.

But it’s the Dillons who hold all the cards: relatives, relative success in the corporate boardroom and the desire to keep racing with rich men’s blessings. They hoped, all these years, they’d find a way to break through and actually prove themselves worthy of NASCAR superstardom.

In the end, they’ll earn a consolation prize: ending their careers as two very rich men. It’s too bad fans don’t prize the value of athletes; they value the success that’s supposed to get them there.

Sound like the theme of another NASCAR flop this summer? Turns out the In-Season Challenge and Ty Dillon aren’t so dissimilar after all.

Did You Notice? … Quick hits before taking off …

  • With 15 races left in the year, Ryan Preece’s average finish stands at 17.1. That’s nearly four positions better than his previous career high (20.8). Also consider one of his RFK Racing teammates, Brad Keselowski, has had arguably the worst season of his career, and I feel Preece deserves more credit. It’s an expansion team that has overachieved and sits with the potential to earn one of the sport’s more unlikely playoff bids in recent history.
  • Denny Hamlin enters this crown jewel race at Indy hot at the right time. Dover Motor Speedway’s race winner has had so much heartbreak at the Brickyard: the 2020 crash, the contact with Chase Briscoe on the road course the following year and another DNF in 2024. If a track ever owed a driver one … it feels like Denny’s due.

Follow Tom Bowles on X at @NASCARBowles

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Tom Bowles
Majority Owner and Editor in Chief at Frontstretch

The author of Did You Notice? (Wednesdays) Tom spends his time overseeing Frontstretch’s 40+ staff members as its majority owner and Editor-in-Chief. Based outside Philadelphia, Bowles is a two-time Emmy winner in NASCAR television and has worked in racing production with FOX, TNT, and ESPN while appearing on-air for SIRIUS XM Radio and FOX Sports 1's former show, the Crowd Goes Wild. He most recently consulted with SRX Racing, helping manage cutting-edge technology and graphics that appeared on their CBS broadcasts during 2021 and 2022.

You can find Tom’s writing here, at CBSSports.com and Athlonsports.com, where he’s been an editorial consultant for the annual racing magazine for 15 years.

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