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DI 30 Under 30 2023: Kieffer Simpson

Kieffer Simpson grew up idolizing his grandfather, John Ulrey, a Super Stock racer who nearly went Pro Stock racing like his fellow Hoosier, the late Bob Glidden. Ulrey’s racing endeavors inspired Simpson to start racing Jr. Dragsters when he was old enough, and nearly 20 years later, he continues to race as a tribute to his grandpa. 

[Editor’s Note: This story originally appeared in DI #185, the 30 Under 30 Issue, in Nov/Dec of 2023.]

“He was my biggest example of why I wanted to go far in racing and do it for the rest of my life,” says Simpson, 29. “Him and Bob Glidden were best friends, and an opportunity came up for one of them to go Pro Stock racing. They just wanted him, not him and all of his brothers. My grandpa said, ‘No, you take me and my brothers or you don’t.’ He chose to ride with his brothers. That was one of my biggest motivators. I don’t know where I’m going, but I always want to be drag racing forever.”

Simpson dipped into his college savings fund to buy his first Jr. Dragster, a move that had a domino effect as Simpson’s four younger siblings eventually got into Jr. Dragsters as well. Between index racing and heads-up Outlaw 330 competition, Simpson racked up numerous wins, championships, and other accomplishments driving his own family cars or driving for other families. He also helped the Indianapolis Raceway Park team win the NHRA Jr. Drag Racing League Eastern Conference Finals as part of a group that also included past 30 Under 30 honorees Devin and Nick Isenhower. 

Simpson also picked up experience as a crew member on an NMCA Nitrous Pro Street team and an NMCA Pro Mod team. While working with these teams, he met his now fiancée, 2019 30 Under 30 honoree and multi-time NMRA champion Haley James. In another moment that helped shape his future, Simpson got a behind-the-scenes look at Don Schumacher Racing’s graphic design setup, which inspired his college studies as well as the launch of Kieffer Simpson Designs. 

Simpson’s future father-in-law, Dwayne James, took notice of Simpson’s hard work in the industry and as a crew member on the team’s Ultra Street car. When Haley qualified No. 1 at the Yellowbullet Nationals, Dwayne told Simpson he was looking at buying a second car and wanted Simpson to drive it. Simpson took the opportunity and ran with it, reaching the final round in Ultra Street at the 2021 Snowbirds at Bradenton before a breakout full rookie season in 2022. Highlights included numerous holeshot round wins and a win at Donald Long’s Sweet 16 5.0 at South Georgia. 

“We don’t run NHRA races, so I would assume that it feels like winning the U.S. Nationals to an NHRA driver,” says the Speedway, Indiana-based driver. “That is kind of our ‘granddaddy of them all.’ It’s obviously a very prestigious event. If you race in it, it’s a very, very intense feeling. At the time there was just a lot of personal stuff going on with some family stuff and it really meant the world when I won that.”

Simpson closed out the 2023 season with a hot streak that highlighted by a semifinal finish in Street Fighter at the Haltech World Cup Finals at Maryland and a runner-up finish in Quarter-Mile Elite at the Mod Nationals at Bradenton. He and James have also worked hard on their new business, 4.44 Custom Apparel. 

Simpson’s big-picture goals include driving a Funny Car, Pro Mod, or Pro 275 car. But like his grandfather, Simpson realizes racing isn’t just about him. He’s determined to help others accomplish their goals, whether that’s his fiancée or his youngest brother, Klein, who races Jr. Dragsters when he’s not crewing on the Haley James Racing entries. 

“It means a lot to me when I see that kid win because he’s the youngest of five and he’s been through a lot, so it’s awesome when he just gets to focus on himself and win,” says Simpson, who thanks his fiancée, Haley, and her father, Dwayne; his mother, Kelli Ulrey; brother Klein, crew member Johnny “Drama” Maguda, and his “papa,” John Ulrey, along with a long list of sponsors and supporters.

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This story was originally published on February 19, 2024. Drag Illustrated


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