But his decision to test the free agent market is based on so much more than wins and losses, and that's why Stewart might very well walk away from a team that has currently established itself as the best in NASCAR.
The two-time NASCAR champion embarked on a whirlwind media tour to explain his decision, joking at one point he'd talked more with reporters at Talladega Superspeedway last weekend than he'd spoken to his own mother over the past two years.
He's won 32 races and a pair of championships with crew chief Greg Zipadelli by his side and car owner Joe Gibbs staunchly in his corner -- no matter the drama and distractions.
Even Stewart, who was humble and humorous during media availability last weekend, was adamant there's no compelling reason to leave JGR when his contract expires at the end of 2009.
"It's not that we're looking to leave, there's nothing wrong," he said. "Nothing's broke, nothing needs to be fixed. Everything is really good where we're at right now."
But it's not so crazy for Stewart to listen to offers, with many dangling team ownership options.
"I think we're stupid to not look at what's being offered," he said. "It doesn't cost a dime to listen, so we're definitely interested in some of the offers that have come across. To the best of my knowledge, I've never seen or heard about offers like this. It's something that I feel like, to be right to ourselves, we have to take the opportunity to at least explore those options and listen to what everybody has to say."
Fair enough.
Now whether he actually takes one of the offers -- which could make him NASCAR's highest-paid driver and give him a guaranteed role in the industry long after he hangs up his helmet -- remains to be seen. But the decision could come down to more than just winning.
Stewart has been smart with his money and has enough tucked away to retire today and still maintain his current lifestyle. But he's also built a small empire, collecting a handful of race tracks and fielding cars for four different drivers at Tony Stewart Racing.
He also has his own public relations firm in True Speed Communications, plus other business interests. Running all that requires money, and by exploring free agency, Stewart is driving up his selling price. No matter where he lands, it's going to cost Gibbs or any other team a ton of cash to sign him -- certainly enough for Stewart to support his diverse business portfolio for a long time coming.
Then comes the ownership aspect. Being in charge appeals to him, and running a race team gives Stewart a challenge away from his own race car.
"I never thought (ownership) would even be an option, but I have to admit -- that is something that has been intriguing about this so far is the possibility," he said. "I enjoy the challenge of trying to help a part of something that grows, and we've been a part of that as a driver at Joe Gibbs Racing.
"The idea that there's that potential, that we might have that opportunity to be a car owner, is something that is very exciting. There's not just one, but there's a couple offers out there that have offered that. To me, I don't remember anybody being in that situation and to me, it's pretty humbling."
Taking on that responsibility also would assure Stewart a place in the garage when he decides to stop driving.
Despite his moaning about the NASCAR grind -- it's a taxing 38-race schedule that's littered with testing dates, sponsor appearances and promotional work -- it has become Stewart's norm over the past decade. He turns 37 next month, and isn't likely to drive at this level another 10 years.
When it's time to get out of the car, there might not be another reason for Stewart to return to the Cup garage. Many of NASCAR's longtime stars have moved into the broadcasting booth, and with his brutal honesty and sharp wit, Stewart would be a natural.
But at his core, Stewart is not a talking head.
He cares deeply about racing and loves being involved at every level. He understands cars, isn't afraid to get dirty and is more comfortable in a garage stall than he would be behind a camera. For him, NASCAR ownership is a natural fit.
"Tony has networked his entire career," Dale Earnhardt Jr. said. "He has a lot of relationships with people that would serve him well should he decide to become a Cup owner. I think he could accomplish his goals however he wants to stack it up."
It's unlikely that he wants to do it like Jeff Gordon, who has equity in at least two cars at Hendrick Motorsports. For Stewart, it's about being the boss.
It's not clear what offers Stewart is sifting through. The only known offer is one to purchase the struggling two-car team at Haas-CNC Racing. Team owner Gene Haas began serving a two-year prison sentence for tax evasion in January, and his two cars have run at the back of the pack this season.
Stewart could bring stability and sponsorship to that organization, which is aligned with Hendrick and has a ton of potential. It also would reunite him with Chevrolet, which has a strong relationship with Stewart even though Gibbs switched to Toyota this year.
Technically, Stewart has two years to decide what he wants to do. He's yet to ask to be released early from his contract, and Gibbs has indicated the team isn't quite willing to part with Stewart before the end of 2009.
In fact, Gibbs plans to push hard to keep Stewart on his roster. He doesn't have ownership to offer, at least not in JGR, but he does have winning race cars. At the end of the day, he believes that's ultimately the most important thing to Stewart.
"It's been a great ride," Gibbs said, "and we don't want it to stop."
SAFER barriers going into Lowe’s backstretch
