Every few years toward the back half of the 2010s and early part of the 2020s, it seemed that there were rumors of 1996-1997 Indy Racing League champion and three-time NASCAR Cup Series champion Tony Stewart making a return to the Indy 500, or at least having been offered a ride to compete. He even commented on the possibility several times.
Stewart is one of five drivers to attempt the Memorial Day Double: IndyCar's Indy 500 at Indianapolis Motor Speedway and then the Cup Series' Coca-Cola 600 at Charlotte Motor Speedway on the same day. He is the only driver to fly from Indy to Charlotte and complete all 1,100 miles on the same day, doing so in 2001 with finishes of sixth and third place, respectively.
Even after stepping away from Cup Series competition after the 2016 season, the Columbus, Indiana native has competed in a number of different forms of racing, so he has never truly retired. He ran all three seasons of the Superstar Racing Experience that he helped to start from 2021 to 2023, and he still competes in NHRA drag racing.
Stewart left NASCAR completely after the 2024 season, with Stewart-Haas Racing shutting down before fellow co-owner Gene Haas opted to remain in the Cup Series and Xfinity Series with Haas Factory Team.
But despite Stewart being as disconnected as he has arguably ever been from NASCAR, he was recently linked to a return to the sport.
Kaulig Racing plan to run a "Free Agent Program" in their fifth truck during Ram Trucks' first season back in the Truck Series, and Stewart's name has been mentioned as a possibility for what would be his first NASCAR start on any level in a decade.
He did not comment on the rumor, but the team have done nothing to stop the speculation with several big announcements likely looming as they look to fill that truck for all 25 races in 2026. Stewart has not competed in a Truck Series race since 2005.
As we've discussed, however, it's not the first time Stewart has been linked to what would be a sensational – and unlikely – return.
The Indy 500 rumors, however, never came to fruition.
"Unfortunately, I feel like that ship has sailed," Stewart admitted to Beyond the Flag during an interview in 2021. "It’s hard to try to revive an IndyCar career at the age of 50."
Stewart is now 54 years old, so while four-time Indy 500 winner Helio Castroneves might still be doing it (and remaining competitive) at 50, that ship has indeed sailed for "Smoke".
"Twenty years ago, it was a little easier to come in there and drive those cars on a one-off deal, but the fields are so strong, and the details of being fast in those cars and the little details you have to do to be good all day long in those, you can’t just show up and do a one-off race and expect to win the race or to have a shot to win," he admitted in that discussion from four years ago.
Stewart competed in the "Greatest Spectacle in Racing" five times and finished in a career-high fifth place in his second attempt in 1997. He made two front row starts in 1996 and 1997, doing so from the pole position in 1996 after Scott Brayton was killed in a practice crash after qualifying on pole.
"I’ve run it enough times, and to just do it and make the race and be a part of it isn’t enough for me," he continued. "Been there, done that, bought that t-shirt and all that. But the only way I would do it is if I felt like I had a legitimate shot to win the race, and I don’t think I can put together a scenario and a program to get myself in that situation."
However, don't think for one second that he didn't enjoy being back at the track for the 105th running of the race in May 2021 with four-time winner A.J. Foyt.
"Man, that is like taking a kid to a candy store, to sit there and go to one of the greatest races in the world, to be there with your all-time hero," Stewart said. "I don’t know how it could be better than that, other than if we would have won the race and got to stand in victory lane together. That’s the only thing that would have made that day any better.
"But to spend the day with A.J., to bounce around between the pit boxes, the car that I was actually the co-owner of was the No. 1 car [driven by J.R. Hildebrand], but sitting on that No. 14 box with him, and then during the pit sequences, we were off on laps enough that I could be there for the pit stop for the No. 14 car, unplug my headset, run down to the No. 1 car, be there in time for that pit stop, and be able to get updated on both strategies for those two cars."
Castroneves won that race to become the fourth four-time winner in Indy 500 history, joining Foyt, Al Unser, and Rick Mears.
"It was a fun day," Stewart concluded. "And like I said, how do you not have fun hanging out with somebody like A.J. Foyt the whole day at one of the greatest races of the year, at an event that he was a four-time winner of and that he is most known for?"
Stewart returned to the Indy 500 in 2025 as a member of the Fox's coverage team. But while a Truck Series return might well be on the cards, it probably goes without saying at this point that we should not expect him back in an Indy Car for what would be the first time in a quarter of a century – and the comeback of a lifetime.