A Checkered Legacy

How will history remember Tony Stewart after a two-decade NASCAR career filled with brilliance but complicated by controversy and tragedy?

- Ryan McGee

Tony Stewart’s fans are getting antsy. There are 20 people sitting in a locker room at Texas Motor Speedway—accountants, lawyers, housewives—all wearing customtailored firesuits and glazed in sweat after driving a genuine Sprint Cup car around one of NASCAR’s fastest tracks. Each has donated $6,500, with the promised payoff of hanging with Stewart for a day at an event called the Smoke Show. He’s been doing it for nine years, raising more than $1.7 million for the Speedway Children’s Charities.

But this year the event’s namesake is running late. Like several hours late. The participants understand it’s because his plane, inbound from Charlotte, North Carolina, had a mechanical issue. But that isn’t keeping them from looking at their watches. “I love him so much, but damn, dude,” one participant says. “I’ve got a lot of s--- I want him to sign today. His career is almost done. Who knows when I’ll get to see him again?”

As if on cue, the racer walks into the room dressed and ready, his smile and his hands both outstretched. “What are y’all doing just sitting around? I thought we were driving race cars today.” Fans gasp. Hands involuntarily clap. Angst to awe: a perfect illustration of the Tony Stewart experience.

On Nov. 20, when the checkered flag falls on the NASCAR season in South Florida, it also will fall on Stewart’s 18-year Cup career, one that has produced 49 wins and three championships. He’s the only man to own Cups sponsored by Winston, Nextel and Sprint. Two decades of brilliance punctuated by controversy. The angry kid who arrived as a Busch Series part-timer in 1996 covered in Indiana red clay has given way to a gray-in-his-temples 45-year-old man—not exactly mellowed but at least more evenly keeled, balanced out by mangled legs and a conflicted heart.