LEBANON, Pa.: Chris Windom was starting to get a little anxious about his winged Sprint Car plans heading into the upcoming 2025 season.

Heading into the 2024 season, Windom inked a deal to run the Tony Vermeer No. 55 on the highly competitive High Limit Racing circuit. It was as tall order for only his third season in winged racing.

The team struggled, and things were dragging through the offseason with no firm plans in place. On Friday, it was announced that the 33-year-old driver and Vermeer had parted ways. A couple of hours later, the Indiana ace had a deal in place with Jason Sides and Sides Motorsports to run the World of Outlaws NOS Energy Drink Sprint Car Series next season.

We caught up with Windom via phone and discussed a variety of topics, including his 24-hour turnaround, struggling the first three seasons, social media, and running with the Outlaws in 2025.

SCU: The split with Vermeer has been rumored for quite some time. When did this happen, and how did you end up pairing with Jason Sides and Sides Motorsports?

CW: It was actually last night. The last 24 hours have been hectic for me. To start with, Jason reached out to me a couple of weeks ago, probably around the time Landon was out of the car and asked me if I had committed yet. I said, ‘I’m not sure yet. I haven’t heard anything.’ As you know, most people have their deals done by the middle of November for the following year, and I let November go by and didn’t hear anything. I talk to Clinton Boyles quite a bit — we have a good relationship — and he hadn’t heard one way or the other. It got to the end of November, and I reached out and said, ‘Hey, we’ve got to get on a call to get our plans and schedule worked out for next year.’ Another week went by, and we are damn near the middle of December. I got on a call yesterday, and we still couldn’t get a definite answer on plans for next year, so it kind of put me in a spot to where … nobody said one way or the other. I know everybody loves to use the term, ‘Mutually parting ways,’ but I would say it came to that as much as it could. I can’t wait until 2025 to figure out my plans, so I reached back out to Jason, and he was completely onboard and excited for it. We’re going to do the Outlaw deal, and I feel good being able to bring NOS to his team to help those guys out a little bit. Those guys have been on the road for a lot of years and have a lot of experience, so I’m excited about it.

SCU: Going to the World of Outlaws … is that something you saw yourself doing this year, or really at all in your future?

CW: No, I didn’t. It wasn’t totally out of the question. Even with Vermeer, we kicked around Outlaws or High Limit, but, no, I can’t say I saw myself there. It’s pretty cool to say you are going to be able to do the Outlaw tour, and it’s something I always looked up to even being a non-wing racer. It’s the pinnacle of dirt racing, and it’s pretty cool.

SCU: This has been a difficult three years in winged racing, and you’ve taken some heat on social media and various podcasts for your performance. You are a reserved guy, so how do you deal with that?

CW: At the end of the day, it pissed me off a lot more the first year than it has the last couple of years. Look, anybody on social media gets dragged through the dirt. I don’t care who you are. It’s the nature of it, and that’s just how people are on there. Honestly, I try to read as little as possible at this point. I have full confidence in myself. I know I can drive a racecar whether it has a wing on it or not, and I just feel like I need to get settled into a situation to find that success. Unfortunately, it’s been different circumstances every year. The first year was with Hayward … no one planned to split up, and it just came to that because of financial reasons. Then, we went and ran the 4-Car, and I feel we got better, but ultimately, I jumped in with the All Stars and went right to High Limit. You know how tough the competition in High Limit was, and not only was it my first year on a tour of that caliber with that many good cars, it was the same with Clinton and the whole team. It didn’t go how we planned. I’m not trying to act like we were great, by any means, but I still have full confidence that I can be successful doing this given the right situation. To answer your question, I pay as little attention to it as possible.

SCU: What is the biggest thing you have to overcome and improve on to make this work and progress as a winged driver?

CW: Initially, I would say a lot of it, especially on big tracks, is aggression level, dirty air and how to put yourself in a good position. Not make a wrong move and give up two laps and then need to try and make it up again. It’s more of a chess game in winged racing than it was in Midget and Non-Wing racing. You could drive right up on a guy’s bumper and drive by him in the next corner if you needed to. Winged racing is more timing and aggression, and that’s probably one thing I had to improve on and still need to improve on. Ultimately, it’s sticking it out with somebody for a couple of years to learn together and get better together. I’ve jumped in three different cars with three completely different teams with three different motors and three different crew chiefs … it sounds like you are making excuses, but that, definitely, matters in winged racing.

SCU: The star power with the World of Outlaws is the best in the sport. You are going to be competing against David Gravel, Carson Macedo, Donny Schatz, Buddy Kofoid, Sheldon … what are your expectations with this team and what do you hope to gain in 2025?

CW: The top seven-eight guys with the World of Outlaws are the toughest guys in the country. My goal is to be competing in that realm as soon as possible. I don’t think, by any stretch of the imagination, we should go out and win our first race together, but I feel confident enough in myself that if we can jell well … You know, I saw speed in their car a lot of different times last year. I think they set quick time in their first race at Volusia. Like I said earlier, if you can get the whole package together and settle into something, it can ultimately turn out good.