Emotion welled up for Chris Windom as he climbed from his race car at I-55 Federated Auto Parts Raceway Park.
All the hard work. All the countless hours. All the hundreds of races in a Winged Sprint Car without a win. The commitment had finally paid off.
Trips to Victory Lane came often for Windom in the early portion of his career. The Canton, IL native mastered the Non-Wing ranks and became one of only eight USAC Triple Crown champions.
But in the early 2020s, Windom pivoted his focus to Wing Sprint Cars. The race cars may be fundamentally the same, but strapping a pair of wings on one creates an entirely different beast. For Windom, it was like starting from square one.
“To be honest, it’s almost kind of like learning how to drive a race car again,” Windom said. “You have so many habits, for me at least, in a Non-Wing car that you develop, and they just really don’t transition into a Wing car as far as the aero and just the way you make moves and passes and the way lines change so fast. The list can go on and on and on.”
Windom wound up hitting the road with the All Star Circuit of Champions (ASCoC) in 2022 with Hayward Motorsports. The year brought a handful of highlights, but it was primarily a season of struggles and learning. He didn’t set unrealistic goals. He knew it would be a tough transition. But even with keeping his expectations in check, going from being a nightly contender to the occasional top five isn’t easy mentally for any racer. The swap to wings brought plenty of bumps and bruises but also fueled Windom’s competitive fire.
“I think it was even tougher than what I thought as far as the expectations were,” Windom admitted. “So, I can’t say it was fun those first few years going in and knowing I probably don’t have a chance to win the night. We were just trying to learn, and that’s not something I’ve really had to deal with for the last 10 or 15 years. So, it’s definitely tough, but at the same time it makes me want to go even more almost because I want to keep doing it until I’m successful at it. That’s just the mentality I have.”
Motivated by an unwavering desire to get to the top, Windom got to work. Eventually, his efforts led him to an opportunity in 2025 with Sides Motorsports on the World of Outlaws NOS Energy Drink Sprint Car Series tour. Even though he’s reached the sport’s biggest stage, there was still plenty to learn as his rookie campaign sent him to several new tracks with a team that doesn’t operate on the same level of budget as some of their competition. Like an NFL quarterback, Windom spent plenty of his weeks watching film.
“My first year on the Outlaw tour last year, I went back every week before we would go somewhere and watched the year prior from Qualifying to Heat Race to Feature just because I hadn’t been to a lot of those racetracks,” Windom explained.
Fast forward to August, and the 35-year-old finally broke through. Windom led all 40 laps of the Night Before the Ironman and put the Sides Motorsports NOS Energy Drink No. 7S in Victory Lane.
Not only was it a special first triumph for Windom, but it also put Jason Sides back in World of Outlaws Victory Lane for the first time in a decade. It hasn’t been the easiest road for “Double Down” as injuries forced him out of the seat and onto the wrenches in 2022, the same year Windom’s wing journey began. But both Windom and Sides remained committed to their efforts, united along the way, and beat the best Sprint Car drivers in the world.
“I don’t know if it really sunk in the first day or two because we had to go back and race the next night and then drive all night to get to Knoxville,” Windom said. “But I think it set in a little more the first night we got to Knoxville and saw everybody and how many people came up and congratulated me or Jason or both of us at the same time. You see how many people are really in your corner or cheering for you.”
The victory also made Windom part of a very exclusive club. Before his I-55 score, only Tony Stewart could claim to be a USAC Triple Crown champion and a World of Outlaws Feature winner. That group grew to two, a meaningful moment for a man who spent time driving for Stewart.
“That honestly was really special to see,” Windom said of sharing ground with “Smoke.” “I don’t necessarily keep up on stats on everyone or myself for that matter. I haven’t had any great stats to look at the last year or two, so to see something like that come up, that’s pretty special because Tony was someone I always looked up to racing. I actually was fortunate enough to drive his Non-Wing car for a while and always had a good relationship with him, and he’s obviously one of the best race car drivers that’s ever come about.”
One win is nice, but Windom’s hunger isn’t satisfied. This is a driver that’s accustomed to competing for victories on a nightly basis and going after championships. Like any successful racer, one accomplishment feeds the desire for the next.
“That’s just the kind of mentality I had when I set out to do this, that I wasn’t going to quit until we won an Outlaw race or were successful at it,” Windom said. “And I don’t mean I’m quitting now by any means. I’m just saying that we would get super frustrated and have been super frustrated, but it’s just the competitive drive in me, I guess. I’m not going to quit at this until I figure out how to make it work.”
Windom continues the 2026 World of Outlaws NOS Energy Drink Sprint Car campaign with Sides Motorsports this weekend in Minnesota at Ogilvie Raceway on Friday, Aug. 21 and Jackson Motorplex on Saturday, Aug. 22. For tickets, CLICK HERE.
Where can you watch every World of Outlaws race? Live on DIRTVision.
Where can you see the World of Outlaws in 2026? Click to see the full schedule.