Miles Ahead – Aydan Bailey Makes Home State Stand at Sick Michigan Miles Presented by Driven Racing Oil to Earn First Drag and Drive Event Win!
When your father is one of the biggest names in drag and drive, it’s going to take something special to break out of his shadow. Aydan Bailey’s victory at Sick Michigan Miles 2026 presented by Driven Racing Oil was his spotlight moment.
Aydan is the youngest of three Bailey brothers, a timing factor that helped along his involvement in his father’s racing.
“My dad wasn’t really doing a lot (in drag and drive) when they were younger,” he said. “My first memories of the track are going with him when he was racing Skinny Kid’s Oldsmobile Pro Mod. I never went to Drag Week — it was always the second week of school so I couldn’t go.”
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As Tom began racing Sick Seconds and then moved on to building Sick Seconds 2.0, Aydan was the right age to become more involved. He started with simple tasks like gapping spark plugs but was able to soak up information and experience from some of the older, wiser heads in the shop.
Aydan’s first drag and drive experience was in 2020, when the Bailey boys took the now infamous ice cream truck out to Rocky Mountain Race Week. Later, they went to visit Richie Crampton in Indianapolis, where Aydan got another taste of race cars built for the road.
“We were hanging out with Richie and he let me drive his car back from the restaurant; I thought it was the coolest thing ever,” he said.
Not long afterwards, the ‘Shitbox of Doom’ (as it was known at the time) went up for sale. Tom did the deal, keen to make sure the ’57 Chevy wagon would stay in drag and drive. Unfortunately, the wagon was then involved in a road accident that left Richie and Dom Lagana, who was driving at the time, severely injured. Another passenger, Jake Sanders, escaped with just minor injuries.
Richie rebuilt the car and hosted Aydan for a few weeks, showing him the ins and outs of not just the Shitbox but also race-car building in general. It was a high-speed course in, well, high speed.
“Richie definitely showed me some stuff, that was a chaotic few weeks,” Aydan said. “That was the first car I ever wired, the whole car. I lived at Jonnie Lindberg’s for a month and we had the goal of getting the car ready for Rocky Mountain Race Week 2021.”
Breaking only to return to Michigan for 24 hours for his high school graduation, Aydan put in several sleepless nights to have the Chevy ready. Tom picked the car up and drove west all night to make it to Kansas for the start of RMRW. “I think we left three days after our original deadline,” Aydan said.
Not only were the Bailey family putting a car on track for the first time since a major rebuild, but it was also Aydan’s first time doing drag racing of any kind. His first passes crept down the track, each revolution of the wheels a victory. When the event reached Denver, Aydan was able to clock his first nine-second pass. “I got addicted and now here we are,” he said.
A little over half a year later, Aydan had the wagon back out for Sick Week 2022 Presented By Gear Vendors Overdrive, where his personal best dropped to an 8.250 at 164 mph. He was having a blast until the LS pushed a head gasket on the final day, putting fluid under the tires and resulting in a big crash at the fast end. Aydan was unhurt, a testament to Richie Crampton’s skills as a car builder, but the Shitbox would require a whole new body.
An even rustier shell was located and the Shitbox became the Duece Box (an intentional misspelling based on a t-shirt typo). Aydan returned to the seat, doing a lot of eighth-mile testing as the driving mojo replenished.
The wagon uses a very simple engine combo with a bulletproof driveline. It’s a 6.0 LS truck block with upgraded internals and off-the-shelf Chevy Performance heads. Twin Precision Turbo & Engine 68/70 turbochargers don’t see a whole lot of boost. “It’s a very moderate setup, we are not pushing the platform,” Aydan said.
Motion is delivered through a Rossler Turbo 400, a Gear Vendors Overdrive and a Lindberg-fabricated rear end, all of which can handle way more power than they are receiving currently.
Aydan competed in Drop The Hammer, Roadkill Nights and a Sick Summer event, but there was one event approaching this year he knew would suit the Duece Box perfectly: Sick Michigan Miles 2026 presented by Driven Racing Oil. The wagon’s big slicks and long wheel base make it easy to find traction, even where others may struggle.
“The car leaves on a dirt road,” he said. “We’ve made the top eight at Roadkill purely because it is one of the only cars that can get down. The car is consistent too, we have a good baseline and it will go down any track without changing the tune hardly at all.”
That proved to be the case at Michigan Miles where Aydan was one-and-done every day. Although Evan Uerkwitz looked like providing a challenge at the start of the week, Aydan’s consistency proved hard to beat. Road issues were present, but relatively minor — such as some overheating on day one and a steering A-arm threatening to come off. With a 5.242 average, Aydan secured the win and the Bailey family’s first Sick orange helmet (the burnout one doesn’t count, Tom).
There’s a bit more performance to be found in the motor yet, with Aydan currently upgrading to half-inch head studs so he can squeeze a few more PSI. All going well, it should lead to some seven-second runs in the not-too-distant future.
“Sevens is all I really need,” he said. “I’d like to go faster someday, but right now I’m good where I am. I want to get some experience running at this level before I try to go any faster. I think a crash early on makes you slow yourself down. I was lucky the car held up and it is stupid to risk your life for nothing.
“When you realize what you did wrong, you need to beat into yourself what to do right with a lot of good passes. When you are going down the track, it’s all reactions, so you need to be doing what you need to do without thinking.”
That’s a calm head for a 22-year-old, but don’t believe Aydan hasn’t inherited his father’s competitiveness.
“Michigan Miles was the first win for me and for a Bailey family member at a Sick event. I may not be able to run fives but at least I can say that.”
Written by Derek Putnam. Photos courtesy of Sick the Magazine.
If you have thoughts / feedback / ideas, please e-mail us at derek@sickthemagazine.com