“She said YES” - When Tony Stewart got engaged to Pennelope Jimenez, years before marriage with Leah Pruett

In November 2017, three-time NASCAR Cup Series champion Tony Stewart surprised his then-girlfriend Pennelope Jimenez with an engagement ring. Stewart shared the exciting news on social media to celebrate the moment, although their relationship eventually ended. The former driver is now married to drag racing star Leah Pruett.

Tony Stewart began his NASCAR career in the Truck Series in 1996. Stewart navigated his way up to the Winston Cup Series after securing 11 race wins and 41 top-ten finishes in the Busch Series. In a career span of 18 years, Stewart secured three championship titles, 49 race wins, over 300 top-ten finishes, and 15 pole positions. His final appearance in the Cup Series was in the Ford EcoBoost 400 at Homestead-Miami in 2016, where he finished in P11.

The former champion and Penelope Jiminez got engaged on Thanksgiving Day in November 2017, and Stewart announced the news on his X (formerly Twitter) account. Sharing a picture of what looked like Jiminez wearing a ring, Stewart wrote,

"She said YES!"

Stewart and his fiancee were often seen together during race events. However, they did not end up being wedded. The reason for their separation was never publically declared. Later, Stewart met NHRA start Leah Pruett, and the couple recently announced that they are expecting their first child in November.

In racing matters, Tony Stewart's co-owned Cup Series team Stewart Haas Racing announced its closure at the end of the 2024 season. Despite the team's closure, their #14 driver Chase Briscoe secured a spot in the playoffs after winning the final regular season race at Darlington. However, he could not make it through to the Round of 8.

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Tony Stewart's sole championship driver Chase Briscoe reflects on elimination from playoffs amid SHR's exit

Chase Briscoe secured his berth in the 2024 playoffs after winning the Cook Out 400 at Darlington Raceway. This gave hope to SHR that it could have a last hurrah before exiting the sport. Unfortunately, Tony Stewart's start driver's playoff journey ended at the Bank of America ROVAL 400 at Charlotte this past weekend.

Following the end of the race, Briscoe expressed his feelings on not making it to the next round. He said (via NBC Sports),

"Yeah, it's tough right, to have all the momentum that we had and have it come to an end, it's definitely unfortunate. But yeah, wish we could have kept going for it[...]We knew I think as a team even going into it that this was going to be the one round, that if we get through this round, we really felt like we could get to the final four, but obviously wasn't able to get through this round."

HMS driver Kyle Larson secured the 6th victory for the #5 team this season and is looking good to secure his second Cup Series title. Meanwhile, Briscoe is joined on the sidelines by Austin Cindric, Daniel Suarez, and Alex Bowman. Bowman had initially advanced to the Round of 8 but failed the post-race inspection and was thus eliminated.