Before tying the knot with NHRA star Leah Pruett, NASCAR Hall of Famer Tony Stewart made headlines with a whirlwind engagement to former Playboy model Pennelope Jimenez. The three-time Cup Series champion proposed on Thanksgiving Day 2017, sharing the news with a jubilant social media post. Though the relationship dissolved, the moment remains a colorful chapter in Stewart’s off-track legacy.
Now married to Pruett and raising their first child, Stewart’s past engagement offers a glimpse into the racing legend’s life beyond the asphalt.
Tony Stewart’s Playful Proposal to Pennelope Jimenez
Stewart’s 2017 engagement was symbolically bold. The then-46-year-old racer tweeted a photo of Jimenez’s diamond ring with the caption: “She said YES!” Fans and peers flooded replies with congratulations, unaware the pairing would fizzle within two years.
Jimenez, Playmate of the Month for March 2003 for Playboy, had dabbled in acting and modeling since the early 2000s. Her credits included a harem girl role in The Scorpion King and appearances on The Price Is Right. The San Diego native’s relationship with Stewart blossomed after his 2016 NASCAR retirement, with the couple often spotted at events like NASCAR’s Champion’s Week in Las Vegas.
But beneath the glitz, cracks emerged. Their last public photo together surfaced in October 2018, and by 2019, Stewart had moved on. Neither disclosed the split’s cause, leaving fans to speculate.
From Playboy Model to Drag Racer: Stewart’s Journey to Leah Pruett
Stewart found lasting love in the drag racing world. He began dating Leah Pruett in 2020, bonding over shared motorsport passion. Their 2021 engagement, marked by a massive emerald-cut ring, led to a low-key wedding, and now raising their first child, Dominic James Stewart.
Pruett, a Top Fuel dragster veteran, stepped back from racing in 2024 to focus on motherhood. Stewart humorously honored her absence at a team dinner by holding a cutout of her, captioning the moment: “Even when @LeahPruett_TF isn’t here, she’s still here.”
The NASCAR legend’s romantic pivot mirrored his career evolution. Weeks ago, Stewart won his first NHRA Top Fuel race, becoming the 999th unique winner in series history. Reflecting on the victory, he drew parallels to his 2009 NASCAR All-Star Race triumph, and said,
“It was not about me. It was not about me proving to all the naysayers that I was going to fail with Stewart-Haas. … It was way deeper than that. It was about the guys and the people that we had put together and the people we had kept from Haas Racing, and what it meant to all of us. That’s exactly what Sunday turned into as well (after his NHRA win).”
For Stewart, life’s checkered flags now include fatherhood and drag racing glory. But for fans, his engagement to Jimenez remains a nostalgic footnote, proof that even legends embrace detours on the road to happiness.