On May 26th, 1996, he started his first Indy 500 on the pole, a dream come true for a boy who grew up spinning around tracks just south of Indianapolis.
In 1995, he won the USAC triple-crown championship, which is the top honor in sprint-car racing, and made the giant leap to Indy Car racing."In the bedroom upstairs, Stewart shows off die-cast models of the dirt-track stock cars he grew up racing.There are framed photos of Stewart with his parents, his friend Kid Rock, Dale Earnhardt Sr., and Stewart's blond ex-girlfriend, Tara Roquemore, a small-town Home Depot employee from Georgia before she met Stewart at a sponsor event.With his prodigious stomach, permanent stubble and more than occasional public outbursts, Stewart reminds the faithful of scruffier icons like Bobby Allison, Junior Johnson, Dale Earnhardt Sr. And the recent history of owner-driver experiments is dodgy at best. In the past, when Stewart had one of his famous meltdowns, there was always a staffer or executive happy to humor him, absorb the anger and pick up the pieces for one of the sport's great racers.Michael Waltrip, the two-time Daytona 500 winner, debuted his eponymous racing team full-time in 2007, but its three drivers are still winless, and they struggle every week to break the top 20. "Running a Cup team is a big step for me," he says. But now that Stewart is the boss, who will he bitch to?