In the NASCAR world, there are very few drivers who don’t just race to make a legacy for themselves but to forge the next generation, too. And Tony Stewart, a three-time Cup Series winner, is known for forging the next generation of drivers. His dirt-track roots and no-nonsense edge have quietly shaped careers behind the scenes. But how does Tony Stewart do that?

One former Cup driver recalls how a single, blunt exchange with Stewart flipped his entire approach to the sport and turned his raw talent into something sharper and more enduring. But as the driver looks back now, it’s clear that advice reshaped not just his racing career but also his path long after his career ended.

Tony Stewart’s advice that unlocked a career pivot

Picture this: a young driver, fresh off his dirt-track dominance, got his first big NASCAR test at Memphis thanks to Tony Stewart‘s connection with Penske. It was 2011, and Josh Wise was the young driver. Wise was first hired by Stewart back in 2003 after he dominated the USAC nationals.

And as the test was about to begin for Penske, he called Stewart for some advice: “Hey, I got this test… I need some help, some feedback,” Wise recalls on Throttle Therapy with Katherine Leggie. Stewart’s advice? “You’ll figure it out.” That was it. No over-explaining of anything, just a simple caution about the tire difference, and that was all.

Wise converted that early break into 156 Cup starts from 2011 to 2016, including a career-best 10th at Talladega in 2015. But Wise, when he was running the Cup races, couldn’t articulate his talent, but now he sees the reason why: great drivers often can’t explain their magic.

“There are drivers that can really, deeply articulate [it]… I was probably one of those for a long period where I just didn’t really understand that even the internal strategies that I had developed over time, and how I was implementing those, I couldn’t really articulate them,” he told host Katherine Legge.

In 2017, Wise retired from full-time driving after struggling with low-funded teams like Phil Parsons Racing and The Motorsports Group. Now in 2025, he works as a driver performance consultant for Chevrolet teams, filling what he saw as NASCAR’s “huge void” in driver prep.

“Just the way guys are preparing across the board in every way: physically, mentally, studying, communicating, all these different aspects of what racecar do as athletes,” he explained in a Frontstretch sit-down.

After partnering with Chip Ganassi Racing, Wise coaches star drivers like Kyle Larson and Tyler Reddick, even training Chevrolet’s development program. Stewart’s little advice evolved Wise from a 36th-place points finisher into a behind-the-scenes force, proving articulation wins races off the track, too.

Stewart’s advice changed a driver’s life, but how did he change his own way after meeting his wife, Leah Pruett?

Tony Stewart’s sponsor clashes in new romance

Tony Stewart’s shift to NHRA drag racing not only made him experience what 11,000 horsepower feels like but also sparked a romance with Top Fuel driver Leah Pruett. Don Prudhomme introduced Pruett to Tony via FaceTime in 2019. And after that, Stewart started showing up at her events, and finally, they got married in 2021 and welcomed a son in 2024. But the really interesting story began in their early dating days when their corporate ties clashed. Pruett ran with Pennzoil and Dodge; Stewart backed Mobil 1 and Ford.

“The first one was, she’s sponsored by Pennzoil. I’m sponsored by Mobil 1. That’s the first hurdle. She’s sponsored by Dodge. And then Dodge and Ford. So it’s like, ‘Man, what are we going to do?'” Stewart shared on the Dale Jr. Download. He also secretly involved his public relations (PR) team to hide their relationship from the public and the sponsors.

“We’ll work around it. You know? We said, ‘Hey, when I go to her events, I won’t wear any branding.’ When she goes to my events, she won’t wear any branding. And that’s what we’ve done. And that’s it. Was very successful with that,” he added. It worked seamlessly, letting their bond grow without sponsor issues.

Last season, Stewart even drove her NHRA car for Pruett during her maternity break, winning NHRA Rookie of the Year in Top Fuel. From Josh Wise to his wife, Leah Pruett, this is a nod to how Stewart helps the surrounding people without wanting anything in return.