Tony Stewart’s reflection on his NASCAR career took a poignant turn following the closure of Stewart-Haas Racing’s Cup Series operations. He publicly expressed deep regret over not signing Kyle Larson, a decision he considers one of the biggest missed opportunities of his professional life. Stewart-Haas Racing, once home to drivers such as Josh Berry, Noah Gragson, Chase Briscoe, and Ryan Preece, struggled in recent years, especially after Kevin Harvick’s retirement, which led to the eventual shutdown of the team’s Cup Series efforts.

The prospect of adding Kyle Larson to Stewart-Haas Racing was a topic of much speculation. Larson, known for his exceptional talent and versatility across racing disciplines, had been pursued but never signed by Stewart’s team. Despite Larson’s proven skill at Chip Ganassi Racing, and later his success with Hendrick Motorsports, no deal materialized with Stewart-Haas. NASCAR insider Freddie Kraft addressed this speculation, emphasizing that even a driver of Larson’s caliber might not have been enough to save the struggling organization.

Before joining Hendrick Motorsports in 2021, Larson had already demonstrated his rare combination of speed, determination, and racecraft. Stewart recognized Larson’s potential early on, describing him as a “unicorn” driver. When Hendrick Motorsports signed Larson, the move quickly paid off: Larson won the NASCAR Cup Series championship in his first season with the team, validating Stewart’s regret over missing the chance to bring him aboard.

Tony Stewart openly admitted his regret during interviews, including one with CBS Sports during Larson’s championship run. Stewart’s reflection highlights both his admiration for Larson’s talent and the unfortunate circumstances that prevented Larson from joining Stewart-Haas Racing. While Larson has since built a remarkable legacy with Hendrick Motorsports-currently sitting second in the Cup Series standings with multiple wins-Stewart’s regret remains a significant chapter in NASCAR history.

This story underscores the complexity of motorsports, where even the addition of a top-tier driver like Kyle Larson cannot always reverse a team’s fortunes. Stewart’s experience serves as a reminder of the unpredictable nature of racing and the profound impact a driver of Larson’s caliber can have on the sport, despite organizational challenges.