Tony Stewart’s reflection on his NASCAR career took a poignant turn following the closure of Stewart-Haas Racing at the end of last season, as he publicly acknowledged deep regret over not signing Kyle Larson. With the shuttering of the team’s NASCAR Cup Series operations—once home to drivers like Josh Berry, Noah Gragson, Chase Briscoe, and Ryan Preece—the motorsport community has been left to wonder whether Stewart’s biggest “what if” could have altered the team’s fate. As Stewart remained at the helm through 2023, mainly driven by Kevin Harvick’s ongoing commitment, his eventual step back became more pronounced after Harvick’s retirement and a slump in performance on the track.
The prospect of adding Kyle Larson to the roster generated strong debate among NASCAR insiders and fans alike. While there were discussions at Stewart-Haas Racing about pursuing Larson, who had proven his skill at Chip Ganassi Racing, no deal ultimately emerged. As questions grew louder about what might have saved the faltering team, noted NASCAR insider Freddie Kraft addressed the speculation directly, emphasizing that even a driver of Larson’s caliber might not have altered the organization’s outcome.
Kraft explained in a candid social media Q&A, echoing a sentiment felt throughout the paddock.
Before joining Hendrick Motorsports in 2021, Kyle Larson’s talent and versatility were already apparent, his adaptability across racing disciplines setting him apart. Stewart, well attuned to rising talent, saw in Larson a rare combination of speed, determination, and racecraft. Despite the missed opportunity, Rick Hendrick recognized Larson’s potential and signed him for the #5 car, a decision that quickly paid dividends. Larson not only adapted to his new surroundings but captured the Cup Series championship in his very first season, reinforcing perceptions of his unique capabilities.
The regret Tony Stewart continues to voice is firmly rooted in this context. Speaking to CBS Sports during Larson’s championship campaign, Stewart was frank.
This openness highlights both Stewart’s admiration for Larson and the weight of circumstances that surrounded the team’s decline.
While Kyle Larson has since carved out a legacy with Hendrick Motorsports, chasing double-duty milestones and currently sitting second in the Cup Series standings with two victories, Tony Stewart’s reflection remains a telling chapter in NASCAR history. The story serves as a reminder that, in motorsports, even the mightiest talents cannot always reverse a team’s fortunes single-handedly. Stewart’s regret underscores the complexity and unpredictability of racing, while pointing to the rare impact a driver like Kyle Larson can have on the sport, regardless of organizational challenges.
