"The only disappointment I have": When Roger Penske spoke about failed Indy 500 talks with Tony Stewart

Roger Penske-owned Team Penske has won the Indy 500 a whopping 20 times and is the most successful team in the series. Despite such achievements being able to lure anyone, former IndyCar and NASCAR driver Tony Stewart declined the offer every time, which remains the only disappointment in the 87-year-old's elusive career.

After initial success in karting, Stewart switched to the open-wheel racing scene and simultaneously took part in stock car races. Though he started racing in the Indy Racing League, his love for NASCAR soon started to grow and after his 2001 Indy 500 attempt, he jumped ships to the stock car racing scene entirely.

There Tony Stewart won three championships but his excellence behind the wheel did not go unnoticed by Roger Penske. The automotive tycoon offered Stewart to get behind the wheel of an IndyCar again and finally triumph in the event that had eluded him for long.

However, he rejected the offer, which has remained Roger Penske's only disappointment as he explained in an interview in 2016.

"The only disappointment I have is that he never took me up on a ride at Indy. ... He is a true racer, true grit, and he tells it as it is," Penske recalled [via FOX Sports].

While an offer from Roger Penske himself was tempting, Tony Stewart had his reasons for declining the chance to race in the Indy 500.

---

Tony Stewart revealed the reason for not taking the opportunity presented by Roger Penske

Tony Stewart during qualifying for the Ford Performance Nationals at The Strip at Las Vegas Motor Speedway - Source: Imagn

Stewart's love for NASCAR had urged him to switch to the stock car racing scene entirely. Moreover, this required some sacrifices to be made that the 53-year-old was aware of.

This included giving up on the dream of racing again in the Indy 500 when Roger Penske came calling, as he explained in an interview in 2012. He said:

"The hard part for me was you make that decision when you sign up to do (NASCAR). The decision you make, you have to come to peace with yourself with saying `I'm not going to do this.' That was my childhood dream anyway. It was hard knowing when I signed that (NASCAR) contract that I was writing off the opportunity to go race at Indy." [via ESPN]

Tony Stewart further added:

"Even though it was hard to watch opening day of practice at Indianapolis, I'm enjoying what I'm doing, too, and this is what I want to do at the end of the day. It makes you want 30-hour days and 400-day years and we always want to do more than what we're capable of doing, but the reality is you have to pick at some point and choose your career path. This is what I've done."

On the other hand, Tony Stewart has achieved a lot in NASCAR. He is a four-time champion in the premier class, including two titles as a driver, one as a driver/owner, and one as an owner.

Stewart is also the only driver to have won the championship through a tiebreak in NASCAR history and is a NASCAR Hall of Fame member since 2020.