Tony Stewart Gets Brutally Honest on His Biggest Racing Regret

NASCAR drivers chase glory on the track, battling for podiums and trophies with grins that light up victory lane. Yet behind those moments, regrets can simmer, even for legends like Tony Stewart, whose three Cup Series championships and 49 wins still leave room for unfinished business. This echoes sentiments from Jamie McMurray, who, seven years after retiring with seven Cup victories, admitted, “My biggest regret in racing is not enjoying it.” Such reflections highlight how past misses linger long after the checkered flag.

As the owner of Eldora Speedway since 2004, Stewart’s ties to dirt racing run deep, amplifying those what-ifs in a career packed with triumphs. The historic venue, home to massive events drawing huge crowds, serves as a constant reminder of paths not taken. With Stewart’s history in midget, sprint, and IndyCar championships, his dirt roots add layers to these unspoken regrets. But as an Eldora boss, those weights hit harder, begging the question of what tops his list.

Tony Stewart’s World 100 heartache revealed

In a recent FloRacing interview ahead of the 2025 World 100 at Eldora Speedway with Dylan Welch, Tony Stewart got candid about a lingering thorn in his storied career: “It’s pretty damn high, in all honesty. I mean, especially when you own the racetrack, but it’s, yeah, you know, I never, you know, I led the dream, and Scott Bloomquist and I had one of the best duels at a dream that I’ve ever seen, but yeah, the world, the only time, the first, I remember the first time I came to the World 100, we were literally parked by Earl’s house because there were, I think, 212 entries or something.”

This admission underscores his biggest regret: never qualifying for the World 100, the crown jewel of dirt late model racing held annually at Eldora since 1971. Tony Stewart‘s background in dirt racing dates back to his early days, winning USAC titles in midget, sprint, and Silver Crown cars by 1995.

Stewart elaborated on the event’s grueling nature, noting, “And back then, it was when they had two rounds of single-lap qualifying. And you want to talk about intense qualifying sessions, but yeah, it was I who got to run a non-qualified feature. That was as close as I got. So I didn’t even get to the program to run a heat race.” The World 100’s format, with its massive fields, often over 200 entries, as Stewart recalled, and split qualifying, makes it one of the toughest to crack, drawing the largest gathering of dirt late models globally.

His closest brush came in attempts where he only reached a non-qualifier race, a far cry from his Dirt Late Model Dream battles, like the epic duel with Scott Bloomquist, where he led laps but fell short of victory. Owning Eldora since purchasing it from Earl Baltes in 2004 added irony, as the track he stewards hosts this elusive prize.

The regret stems from Stewart’s deep dirt passion, where he excelled elsewhere, like winning the Prelude to the Dream three times between 2006 and 2009 at Eldora. The 54-year-old wrapped up by affirming its difficulty. “But it’s cool, and it just shows that, you know, the World 100, by far, I feel like, is one of the hardest races to make for sure.”

This honesty ties back to his 1997 Indicate championship and NASCAR dominance, but the World 100’s qualifying wall, demanding precision in a field of elite drivers, left him on the outside, a story of near-misses for the Hall of Famer.

Regrets like Stewart’s show racing’s emotional layers, but they’re just part and parcel of it. Jamie McMurray’s recent revelations echo similar hindsight, offering lessons for fans and drivers alike.

McMurray opens up in career reflections

Jamie McMurray, seven years removed from his 2018 full-time retirement, shared a wish to rethink his path on Kevin Harvick’s Happy Hour podcast. “I wish I could do everything backwards. And what I mean by that is I wish I could have done TV first because if I could have, when I went back to my career, I would have handled things completely differently, whether it was interviews or what I found value in or seeing the other side of it,” he said.

This stems from his FOX Sports role since 2019, where analyzing races revealed the media pressures he faced as a driver with 583 Cup starts and 63 top-fives. His 2002 Charlotte breakthrough as a substitute for Sterling Marlin kicked off intense expectations, shifting focus from enjoyment to performance.

He pinpointed the core issue: “My biggest regret in racing is not enjoying it.” Substantiated by the high-stakes blame game in racing, where team errors hit hard with “your name on the door,” this regret links to seasons like 2011-12’s 72 starts without wins amid Ganassi changes. McMurray’s karting start in 1983 was fun-driven, but professional demands, like his 2003 Rookie of the Year, turned it grind-heavy. His 2010 Daytona 500 and Brickyard 400 triumphs brought highs, yet later years, including 20th in 2018, fueled frustration before his broadcasting shift offered clarity.

These insights add value for current drivers, urging balance amid pressure. McMurray’s 2024 commentary, like Bristol breakdowns on setups, shows how hindsight informs his work, resonating with figures like Kyle Busch. His career is a blend of highs and regrets, encouraging him to savor the ride, especially as he joined CW Sports in 2025.