Not only does that emotional night at Lakeside stand as Stewart’s final victory, but it was one of few races his wife, Jenn, and three kids were able to attend this year.
“It was closure for me at that point,” Stewart said. “To even have the opportunity to get in that car was pretty slim, and then to go out and win, it was just a really cool moment. For myself, [my wife] Jenn, and the kids.”
While the first win of 2020 at Williams Grove was a moment where Stewart proved he could still win at the highest form of sprint car racing, in case suitors for 2021 were taking notice, the final one on Oct. 16 had a much different feel.
By October, Stewart had come to terms 2020 would be his final year as a driver. He had reached the final agreements of acquiring Port City with Rudeen, a process that started when Stewart began expressing anxieties about his future to longtime friend Andy Hillenburg.
“Why don’t you buy Port City?” Hillenburg posed to Stewart, who never even knew Port City, the very place he grew up, was for sale.
“Once I figured out this was for sale and there was a good possibility I was going to get it, I never really struggled with telling myself, ‘This is it,’” Stewart said. “That was another thing that made me think this is the right time and it’s meant to be.”
Things evolved rather quickly for Stewart, who was ready to walk away from it all after the 2019 season. He had been let go from Kyle Larson Racing after one win in 2018 and then let go again, this time from CJB Motorsports, with another one-win effort.
Then, he slowly proved to himself and everyone who doubted he still had it. More importantly, he found enjoyment in racing again.
“I needed that,” Stewart said.
By the tail end of summer, once he proved he could still do it, that incentive carried little weight, because even if Stewart would find another full-time ride, it’d likely be good for only two or three years. That’s when Port City made sense.
“This is going to be something I can do for the next 20 years,” Stewart said.
For those next 20 (or so) years, Stewart’s track duties will include coordinating events and grating clay. First, he will have to learn how to actually use a grater and the science behind how to prep a racetrack.
However, that won’t come before he gets to finally move his family back home and enjoy more time as a dad.
Stewart will leave driving 19th all-time on the World of Outlaws win list at 36 victories. He is also thankful to leave healthy and with a purpose.
There will likely be no more opportunities in a race car for Stewart to maximize again, but there will be plenty of relationships to be handled with care along the way at Port City, particularly within the next generation of racing talent.
“It’s as much [relationship-building] as it is performing on the race track,” Stewart said. “It’s something the younger generation has to be told and taught. I’m looking forward to being a small part and trying to help them learn that side of it too.
“I’m excited about all of it.”