But Stewart also can imagine what it might feel like to be in victory lane at the Daytona 500 both as a driver and a car owner, so it's a risk he's willing to take.
Having recently negotiated a release from his Gibbs contract at the end of this season, the two-time Cup series champion announced Thursday that he will join the team currently known as Haas-CNC as an owner-driver in 2009.
"There's no guarantees that this is going to be successful," Stewart said. "But after sitting down and evaluating what the potential of this team is, I wouldn't have made this decision if I didn't think it would be successful and if I didn't think it had the potential to be great."
Stewart will be given a 50 percent ownership stake in the team, which will be renamed Stewart-Haas Racing. The two-car team currently fields the No. 66 car for Scott Riggs and the No. 70 car for Jason Leffler, and both cars are outside the top 35 in owners points going into Saturday's race at Chicagoland Speedway.
The move had been widely anticipated, but Stewart confirmed it to his current crew members and other Gibbs employees at the team's race shop Wednesday.
"I wondered how it was going to feel," Stewart said. "I wondered how everybody was going to react."
But Stewart said after he spoke, several employees stood in line to congratulate him.
"We could never be mad or hold that against him," said Stewart's longtime crew chief, Greg Zipadelli. "His success, our success as a group, would not be possible without him."
Stewart said the hardest part about his decision to leave was the fact that Zipadelli isn't coming with him. Zipadelli will stay with Gibbs, and may end up being paired with 18-year-old racing phenomenon Joey Logano on the No. 20 team next year.
"For myself, I think you've got to look at what's best for me, where am I most comfortable, and where are my obligations," Zipadelli said. "They're with Joe Gibbs Racing. My guys have supported me and most of them have continued to work with me for 10 years or more. That's important to me."
A plan to stay involved in NASCAR after he's done driving is important to Stewart, who already has several financial interests in racing -- including ownership of sprint car teams and grassroots race tracks.
Stewart and Haas-CNC general manager Joe Custer did not directly confirm the financial details of Stewart's ownership stake in the team. But both Custer and Stewart strongly hinted that adding Stewart's name and fame to the marquee was enough, and he wouldn't be investing a large chunk of his own money.
Is that really enough to warrant giving him half the team?
"He doesn't just put his name on it. He puts his heart into it," Custer said. "What's Tony Stewart's heart worth?"
The other 50 percent of the team is owned by Haas Automation, a California-based machine tool builder. The company's founder, Gene Haas, began serving a two-year prison sentence for tax evasion in January.
Custer said Gene Haas was not involved in making the deal with Stewart. It was approved by another Haas executive, general manager Bob Murray.
Stewart said the team's sponsors and second driver for next season have not been finalized. It has been speculated that Ryan Newman, who currently drives for Penske, could end up as Stewart's new teammate.
The addition of Stewart -- perhaps joined by another big-name driver and some big-money sponsors -- could go a long way toward boosting the performance of the team. They already have good equipment, getting their cars and engines from the Hendrick Motorsports team.
But what if they continue to struggle early on next season? Can Stewart handle running in the middle of the pack after years of running up front and contending for championships?
"I feel like that we have the variables in place to go out and be competitive right away," Stewart said. "At the same time, we know it's a rebuilding process and it's going to be an adjustment period. How long is this adjustment period going to take? We don't know."
Zipadelli said Stewart has matured in recent years, perhaps allowing him to better weather short-term challenges.
"He's done a much better job at controlling his emotions on the bad days, when situations aren't quite to his liking," Zipadelli said. "I think if he doesn't start off with the success he's used to or wants, then when he get it, it's going to be much more fulfilling knowing that he took it from what it is to hopefully what it will be."
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