“I want to be there so bad”: When Tony Stewart candidly spoke about his yearning for winning the Indy 500

Tony Stewart conquered nearly every racing series he raced in, not only as a driver but also as a team owner. But there was one event that the IndyCar and NASCAR legend couldn't crack - the Indy 500.

In 1995, Stewart began his racing career by racing in IndyCar and NASCAR simultaneously, a year after winning USAC's triple crown. In his Indy 500 debut for Team Menard, the Indiana native started in pole position and led 44 laps before a mechanical failure led to a DNF.

In his second year in the open-wheel series, Stewart's performance improved considerably, and he won his maiden IndyCar championship. But once again, he failed to win the Indy 500 despite leading 64 laps of the race. This unfortunate run at the iconic event continued in the years to come, and he never emerged victorious in the "Greatest Spectacle in Racing." Consequently, he stopped racing in IndyCar in 2001 and shifted focus to NASCAR.

In 2012, however, fans of the "Smoke" temporarily rejoiced as Team Penske offered him a chance to race in the 2013 Indy 500. Even though his childhood dream of winning the race hadn't materialized, he declined the offer. In June 2012, Tony Stewart spoke about this unfulfilled dream with Autoweek.

"Trust me: Every May, I sit there and I want to be there so bad. It's still a goal I never got to achieve, as far as winning the Indy 500. The great thing is, I'm still just as much of a race fan when it comes to the Indy 500 as anybody. You still miss it, you still wish you could be a part of it but my career path went a different direction," Tony Stewart said.

After 2001, Stewart's entire focus shifted to the NASCAR Cup Series. He surpassed his IndyCar heroics in stock car racing to win four Cup Series titles - two as a driver (2002 and 2005), the third as a driver/owner of Stewart-Haas Racing in 2011, and the fourth as an owner in 2014.

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The Indy500 moment that Tony Stewart will "never forget"

AUTO: NOV 01 Tony Stewart at Ford Performance NHRA Nationals - Source: Getty

In 1999, Tony Stewart attempted the Double Duty by racing in the Indy500 and the Coca-Cola 600 on the same day. He failed by a mere 10 miles and was physically exhausted. But the fire to complete the job kept burning, leading to a successful 2001 Double Duty outing. He is the only driver to complete all 1100 miles in one day.

Yet, this mammoth achievement isn't Stewart's favorite Indy 500 moment. Instead, his debut at the race in 1997, which he secured with a speed of 233.1 mph, holds a special place in his heart. In 2016, he told the Daily Dayton News:

"The favorite moment is when I qualified for my first 500 in 1996. What made it more exciting was hearing (announcer Tom) Carnegie calling it. You can’t hear that in the car, but when I saw the video of him calling those four laps? Holy crap. That 10-mile run is something I’ll never forget."

In 2024, Stewart shut down Stewart-Haas Racing, citing the intense demand required to run a racing team.