
Wheelin' & Dealin'
Whether Tony Stewart is behind the wheel of his Sunday stock car or at the helm of one of his 14 businesses, the foul-mouthed bad-boy driver–turned–motorsports mogul only knows how to do one thing: Win.
By John Schwarb

The air is dirty. Which is to say, it’s perfect. Eldora Speedway nights are like this, with angular, aging racecars kicking up just enough clay and haze to send every one of the 20,000 spectators home with a dirt epidermis. Dirt pros and dream-filled amateurs have converged here, amidst the corn and soybean fields outside a tiny town in southwest Ohio—past a sign directing travelers to Annie Oakley’s gravesite, past another for the KitchenAid plant where standing mixers are made—for more than a half-century, trying to solve the “Big E.” There is no other place quite like it.
Usually the enormous rear spoilers and giant rear tires are scratched and completely caked with mud, but tonight is different. The cars are showroom-spiffy, decaled and numbered as if this were a Sunday NASCAR race. The lively fans have filled the oval to capacity and then some. And the big-time drivers who attend this annual race, stranded an hour away from their private planes parked at the Dayton airport, are linked not only by their shining careers but by their undeniable right to hold a grudge against their host: In 2000, he bloodied the lip of Robby Gordon ($30 million in Sprint Cup winnings to date) after on-track conflict turned into off-track shoving; he ran Matt Kenseth (18 wins, $66 million in prize money) into the grass at Daytona, after they had bumped around all afternoon; Jeff Gordon, one of the calmest and most successful drivers of all time, once threatened him with a one-way trip into the wall. It is an unlikely party.
But there he is—a two-time Sprint Cup champion, longtime NASCAR bad boy, and up-and-coming mogul—glad-handing and smiling for the pay-per-view cameras, beloved everywhere he turns. When Tony Stewart asked, these drivers took a midweek night in the middle of their racing season to travel to a half-mile spit of dirt in the middle of nowhere to raise money for a charity picked by him. They came not because of who Stewart was, but because of what he has become. At 38, he is one of the most powerful figures in a motorsports league whose events routinely draw more weekly live spectators than the Super Bowl. No longer just a loudmouth driver, Stewart has become some kind of scruffy CEO, a mogul commanding a growing empire of 14 businesses, from racing teams and small tracks to a company that sells beef jerky.
But if the upstart businessman from Columbus, Indiana, is now the NASCAR star with the Midas touch, he isn’t sharing any of it tonight. He glides his No. 14 car through the speediest groove almost as if on skates rather than racing treads, gunning for the front. He is driving as hard as he can.