For Todd Gilliland, It’s Risk Versus Reward To The Max On The Streets Of Chicago

Photo by Mark J. Rebilas/Imagn Images

By Dennis Krause

With the first two attempts plagued by rain, the NASCAR Cup Series heads to Chicago this weekend hoping that the third time is a charm as far as the weather is concerned.

Todd Gilliland, driver of the No. 34 Front Row Motorsports Ford Mustang Dark Horse, scored a seventh-place finish on the 2.2-mile Chicago Street Course last year and is looking forward to a, hopefully, dry race this year.

“First off, I’m excited to go back to Chicago. It’s definitely a really fun place, a fun city to hang out and all that. I’m looking forward to going back there. Myself, I don’t necessarily mind the rain. We’ve ran well there in the past there, but on the flip side of it I’m ready for Chicago to have a weekend go as planned and hope the fans can experience all of that fun stuff behind the scenes. I think the whole experience would be much smoother without rain and I’m hoping that for the fans for sure.”

Photo by Jared C. Tilton/Getty Images

With its tight confines, the Chicago Street Course lends itself to plenty beating and banging. But according to Gilliland, balancing aggression will be key to surviving the 75-lap race.

“I think Chicago is probably the biggest risk vs. reward racetrack that we go to because being aggressive doesn’t really pay off there. Whether it’s getting as close as you can to the apexes, which are all walls, using up all the exit room, but on the flip side of it the risk of it is massive because you’re not gonna run off and get stuck in gravel or hit a curb. You’re gonna hit a wall or a tire barrier, so it’s definitely about managing all that stuff. There’s a time and a place to put it all on the line, but you have to finish the race. The toe links and suspension and all that stuff has to be intact, so that’s the main goal and definitely balancing aggression is big.”

According to Gilliland, racing the Chicago Street Course is like playing chicken with yourself compared to other tracks where a driver can get underneath another driver and move them up the track to make a pass.

“Here, you’re not gonna get away with it. If you go in there side-by-side, even if you’re the guy trying to make a pass and you make a mistake going into a 90-degree corner, if you lock up the inside tire, you could easily stuff yourself and the guy you’re trying to pass in the tire barrier. You just really, really have to balance it – risk versus reward. 

“It’s definitely a tougher place to pass,” Gilliland said. “There are obviously a lot of really good braking zones, but it’s almost like playing a game of chicken with yourself. I feel like as a driver you have a good idea of where the grip is at and the balance and what you’re able to do, whether it’s braking or taking the corner or whatever, but you definitely have to push yourself right to that limit, if not past, to make a pass. It’s definitely not the most comfortable, but it’s risk versus reward to the max at Chicago.”

Photo courtesy of HHP/Jacey Norgaard

The 25-year-old second generation driver doesn’t have a road racing background. However, Gilliland has honed his skills turning left and right through his on-track experience as well as in the simulator.

“For me, I don’t know. I think it’s just been more so race experience. I never grew up go-karting or anything like that. I’ve always ran ovals my whole life. I remember my first road course race in the K&N Series not too long ago, but on the other side of it, since I’ve been in the Cup Series I’ve had a couple of go-karts and been out to the go-kart track a little bit. 

“At the same time, it’s not necessarily the same,” Gilliland added. “I’ve run a ton of laps on the simulator. I think that is probably the biggest thing that I focused on. I feel like just about every driver at the Cup Series level, after three laps at a road course, you’re gonna be fairly close and in the ballpark. For me, just one thing I’ve tried to focus on and be as good as I can at is that first lap. Having a good idea of brake markers, running so many laps on the sim that you know the course like the back of your hand. Stuff like that. The field evens out very, very quickly, but that’s what I’ve been working on myself is hitting the track and being at my best right away.”

Going back to Chicago for the third time, Gilliland says extra film study isn’t necessarily all that important.

“To me, line-wise Chicago is pretty self explanatory because it’s a lot of 90-degree corners. You want to be as far out on entry, you get to the apex as late as you can and then get a straight shot down the next straightaway to most likely another 90-degree corner. Like I said, line-wise it’s not that hard, but a different technique and stuff that we see at a street course with the roughness, the braking and the apex. Like I said, how you angle into them and all that stuff. We’re looking at all of it, for sure.”

Gilliland will drive the Gillo’s Pickles Ford Mustang Dark Horse at Chicago.

One particular challenge the Chicago Street Course presents is that the cars will be pitting the opposite way, with the driver side on the far side of the pit wall. Gilliland believes that setup, along with the tight pit boxes, can open the door to making mistakes.

“I would say, in general, the biggest issue people see is guys turning into the pit boxes too early because also at a lot of these places the pit boxes aren’t real big. I don’t know if it’s a NASCAR thing. When they’re on the left side, they’re more normal for our size of cars, where like at COTA the pit boxes are very small and then Chicago, I don’t remember them to be very big, so you turn in and kind of clip that fourth box. That’s a penalty, whether in or out. 

“Another random thing about the right side pit road is usually they give me a water bottle, tear off, every pit stop because my window is right there and they can give me a water bottle while they’re changing the right side tires, come around and then the guy is out of the way, whereas at Chicago my interior guy would have to run all the way around the car and kind of be in the way and it just wouldn’t work out, so I have to do a little bit different setup on the water bottle and all that stuff. Then at Chicago specifically it’s pretty tight around that last corner to actually get into pit road, so you just have to be smart about making sure that if you’re gonna pit, you get to pit road and then also the pit road light was a little tough to see last year, so all of those things. 

“It’s easy to make mistakes. You have to be on top of your game.”

As Gilliland says, it’s risk versus reward to the max.


Dennis Krause has spent decades covering all forms of motorsports, including over 40 Indianapolis 500s, with stints at WIBA Radio, PIT PASS - Radio’s Premier Motorsports Magazine and Motorsports Minute. Follow him on X @DennisKrause500 or motorsportsminute.bluesky.social or motorsportsminute on Threads or MotorsportsMinute+ on Facebook.

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