The Flaggs’ old connection to NASCAR

Cooper Flagg’s parents, Kelly and Ralph, didn’t just watch NASCAR on television. They drove from Maine to New Hampshire Motor Speedway and camped out for race weekends. This was a regular thing, starting in 1999, and their driver was Tony Stewart, who had just made his Cup Series debut that same year. Stewart was loud, unfiltered, and fast.

So Cooper felt more than comfortable talking about his family’s NASCAR background during an interview at the track.

“I think obviously they are very into NASCAR, and they used to go to all the races when I was much younger, and I think before me as well,” Flagg said. “My parents used to go camp out for the week and enjoy the races.”

Cooper noted that things eventually slowed down.

“My parents both got really busy chasing me around and my other two brothers, so they’ve kind of been away from it for a little while,” he said.

He also revealed that his family idolized Stewart.

“I know growing up, Tony Stewart was the main one in our family that we all loved. I know my mom had a big crush on him.”

Hard to argue with the taste.

Tony Stewart’s versatile racing career left a lasting impression

Smoke has had a stellar career—three Cup Series championships and 49 wins. He won his very first Cup win at New Hampshire Motor Speedway in September 1999. Interestingly, the Flaggs had just started making their annual trip. Timing like that cements a fandom.

The 2011 championship is the one that people still talk about. With ten races left in the season, Stewart wasn’t even inside the top 10 in points. He won five races and went to Homestead tied with Carl Edwards on points, with the title coming down to a tiebreaker: most wins. Stewart had more. It was a comeback that didn’t seem possible until it was, and he did it as co-owner of Stewart-Haas Racing, a team he had built himself.

Before coming to NASCAR, Stewart had already won the 1997 IndyCar championship. Being a title winner in both series puts him on a short list. What made him different, though, was that even at the peak of his Cup career, he showed up to dirt tracks on off-weekends just because he wanted to race. No other driver at his level had done that. His nickname wasn’t merely branding; it was accurate.

NASCAR inducted Smoke into its Hall of Fame in 2020. He retired from Cup racing in 2016 and switched formats. Stewart moved into the NHRA Top Fuel competition and kept winning. On April 12, 2026, he picked up his third career Top Fuel win at the NHRA Winternationals in Pomona. Tony’s currently sitting fourth in the standings.