From Carondelet Park to National Podiums: The Rise of Junior Cyclist Maddox Simmons

For 60 grueling minutes, Maddox Simmons relentlessly chased his championship.

His legs pumped furiously as he repeatedly sprinted up Kanawha Boulevard alongside Haddad Riverfront Park in downtown Charleston, West Virginia, then made successive hard rights on Court Street, then Lee Street, and then Summers Street, before a sharp left on Quarrier Street, a right on Hale Street, and another one back to Kanawha.

Over and over, Simmons repeated this one-mile loop on June 17, competing with more than 75 of the country’s best riders in the junior men’s division (17- and 18-year-olds) of the 2026 US Criterium National Championship. He avoided dream-crushing crashes all around him, weathered pushes from equally determined riders, and found himself in the lead group as the last lap played out.

Simmons is from Glen Carbon, Illinois, and is a member of the Chaney Windows and Doors/Big Shark racing team based in St. Louis. He finished third at the 2025 edition of the Criterium National Championship, and an eventful year of challenges and successes had only steeled his resolve when the 2026 race came around on June 17, coincidentally his 18th birthday. He wanted to win, full stop.

But crit racing can be cruel. A year’s worth of motivated training and an hour’s worth of max effort was undone with a moment’s worth of hesitation. Not hesitation by Simmons, but by the rider between him and lead racer Gregory Debenedetti as they made the last turn, from Hale to Kanawha.

“I was third wheel, and I thought as soon as we went through that turn that I was going to win the race,” Simmons says. “But the kid in the front started sprinting, and the kid in between us let the gap go, so when I started sprinting, there was probably a seven-bike-length gap. It was just that second of hesitation.”

Simmons’s strength is sprinting, accelerating quickly over short stretches, and the finish-line photo shows he got agonizingly close to erasing that gap. His front tire is even with Debenedetti’s seat as they cross. Another 30 meters, maybe, and he would have had it?

“Just another 10 meters, honestly, and I could have had him,” Simmons says. “That’s what lost the race. I should have known to go around (the rider in second).”

***

STILL, THE BIG picture matters here. Simmons is an up-and-coming rider with immense potential, and the Charleston race was a learning experience that can help him get better in the future. Simmons — and those in his corner — are determined to make sure that’s the case.

Owen Gillott, who has been racing competitively since he was a kid in Australia, is a teammate of Simmons’ on the Chaney team. He was in Charleston, helping Simmons prepare and rooting him on during the race.

 

“He’s got a good enough sprint that he almost won it anyway, and the positive thing you can take away from that is everyone who watched it, they looked and went, ‘Maddox could have won that bike race,’” Gillott says.

“The reason he didn’t is twofold. He lost the race because the guy in front of him lost it for him. But if Maddox had taken that wheel and gotten in front of him before that corner, he would have won the bike race.”

Simmons has plenty of wins and podiums on his resume, including several trips to the top step in 2025: the American Criterium Cup Junior Cup, St. Louis’ Gateway Cup Juniors, the Swamp Classic Juniors, and the Tour of America’s Dairyland Juniors. It’s easy to see the potential for bigger and better things for Simmons.

Gillott, 31, definitely sees it. He’s looking to pass on the wisdom and lessons he’s learned over more than two decades of racing around the world.

“I know I’m not as good as I was 10 years ago, so I’m looking for the next generation to help take the next step, and I think Maddox is definitely one of those kids,” says Gillott, who lives in Austin, Texas, and sees a ton of racers.

“He has something special. He does have an insane talent. He’s got an incredible, powerful sprint. If I could do the numbers that he’s doing when I was his age, it might have been a completely different story for me.”

Simmons is just starting to learn the mental side, says Gillott. But he’s headed in the right direction.

“When he gets to 22, I think it’s going to be an absolute lethal combination,” says Gillott. “And he’s going to be cleaning up a lot of bike races.”

***

GILLOTT HAS BEEN where Simmons hopes to go someday: racing professionally full-time in Europe. Simmons is almost there. In fact, coming off a few successful years working with John Singleton at Indiana Cycling Development, Simmons was planning to join a team in Italy in 2026.

“Last year I got to race in Belgium and Italy,” Simmons says. “I met the team while I was over there and raced against them a few times. When I went back home to the US, I kind of realized I really wanted to live in Europe and do this for the rest of my life.

“That was the whole goal, so I just emailed everyone I could, and they responded. They were pretty happy to work with me, and I got a spot on that team.”

 

Simmons was one of only a handful of American kids to get a European contract as a junior. But those plans got derailed.

In February of this year, Simmons was racing in Arizona. It was a new race for him, and he got caught up in a little crash.

“I broke my elbow, and just kind of fell out of love with racing for a little bit,” says Simmons. “I talked to my parents and made the decision that I wouldn’t go to Italy. I joined the Chaney team that month and just started loving it again.”

The ups and downs have been challenging. It’s a good thing for Simmons that he has his parents, John Simmons and Meah Malkowski.

“My family is incredible,” he says. “I have great parents. I can’t do anything without them. I mean, they give me everything. I don’t work, I just train. They send me to Europe, and they pay for everything. Without them, I’m nothing, so having them in my life is just a blessing. I cannot ask for anything more.”

The goal of racing full-time in Europe is inching closer to reality. After nationals, members of the Italian team got back in touch with Simmons, complimenting him on the race. Simmons took the opportunity to see if they had any race openings for him.

“They said they did, so we’re going to figure something out,” he says. “Hopefully I’ll get back over there this year and get a result.”

One of the things Gillott has tried to do for Simmons is share his experiences in Europe. He was there in his early 20s, and the challenges were not limited to what happened on the bikes on that continent, where racing is a way of life for so many.

“I spent two years there and then realized that I couldn’t hack it and came back, but I think he’s definitely got potential,” Gillott says. “He’s not a climber, but there’s a ton of sort of classic racing that he would be really good at. I think he’s just got to find the right team environment to get there, and that’s hard to do as a junior. European teams are very cutthroat. It’s a different environment.”

Racing in Europe means being an outsider, starting with the language. Gillott was on a French team despite not speaking French. His only teammate who spoke English was an Irish guy — who also spoke French.

“I really only had one person that I could talk to,” says Gillott, “and half the time he was chatting with everyone else in French.”

***

MAKING IT IN Europe will be challenging. Simmons has never been afraid of a challenge, though.

He got his first road bike at 13 and competed in his first races soon after: the Vann Knight Tuesday Night World Championship Criterium Series in St. Louis’ Carondelet Park.

“It’s a really fun race that got me into cycling and taught me how to handle my bike and how to race,” Simmons says. “At first I wasn’t the best, but I just kept going back because I loved it so much.”

 

For those who have watched Simmons from his early days on a bike, it’s been kind of amazing to see his growth. Mike Weiss, the owner of Big Shark Bicycle Company, was there for those first days at Carondelet Park. Simmons would compete in the B Series races, but it wasn’t long before he was angling to find his way into the A Series runs, a serious step up in competition.

“You might be doing well in the B Series, but when you go to the A, you got to level up. And at first, generally, it’s just about survival,” Weiss says. “Maddox was definitely kind of cold forging. Like, you hit yourself hard enough times, and you’re going to harden up, right? He’s definitely been that kid who puts himself in stressful situations, and he’s clearly adapting.”

Not just adapting, but thriving.

“When you’re young, you really don’t know what’s under the hood, and nor do we when we’re watching a young kid get better,” Weiss says. “I actually thought for the longest time, ‘This kid’s just too aggressive, and he’s too confident.’ Because he was always wanting to put himself in the line of fire. But now that he’s racing at a professional level, I guess his experiment has worked.”

Weiss organized a local race this past spring in St. Ann. Simmons was the youngest kid in the race, yet he still won it.

“He won emphatically, and it seemed like he won it without any effort,” Weiss says. “He’s beginning to develop the physiology of a professional athlete. You can just tell that his body is turning into lean, powerful muscle.”

It is a rather rapid ascent, going from starting his career at Carondelet Park at 13 to potentially calling Europe home at 18.

“To have the ramp-up he’s had, that’s what is surprising to me,” Gillott says. “I started in under-9s, and I’ve been doing this my whole life. He started only a few years ago, and he’s already at the point that he’s getting second at nationals. He’s getting podiums at national-level racing.”

Gillott points out another big factor working in Simmons’ favor: genetics. Simmons’ mom is a runner, and his dad is a powerlifter.

“He’s got an insanely good physiology, which allows him to be competitive,” says Gillott. “His mom has excellent cardio. His dad is strong as an ox. So Maddox kind of got the best combination of fast-twitch muscle fibers and endurance. He’s just going to get better and better.”

Author: Ryan Fagan is a contributor to Terrain.

Top image: Maddox Simmons in Lafayette Square, one of four stops on his Gateway Cup racing schedule this September 4-7. (Reiss Wegman)