The first time I encountered Tony Stewart was at a bowling alley in Charlotte, N.C. It was early 2004, and he was the baddest thing on four wheels at the time. He had already won rookie of the year (1999) and a championship (2002) at the Sprint Cup level, and in the four seasons he had spent in stock cars to that point he had visited victory lane to celebrate and the NASCAR hauler to get castigated with roughly equal frequency.
He was so good and so volatile that he drew comparisons to baseball Hall of Famer and legendary crank Ted Williams. Williams was famous for saying that he wanted people to say of him, “there goes the greatest hitter who ever lived.” There was talk that Smoke, as Stewart has long been known, would build a similar legacy for himself. In between frames, I asked Stewart, who will retire from NASCAR after Sunday’s race at Homestead-Miami Speedway, what he wanted people to say about him. He said: “That guy got up on the wheel, took that thing to the front.”
Through the course of an unprecedented racing career spanning nearly four decades, roughly $130,000,000 in prize money and countless controversies, Stewart sure did that. At NASCAR’s top level, Stewart won 49 races (13th all time) and three championships (tied for fourth with four others). The only hole on his NASCAR resume is that he never won the Daytona 500.
NASCAR will never see another driver like Stewart, as sponsors have accrued so much power that someone who got in as much trouble as he has over the years would never even make it to the Cup level, let alone endure for 17 seasons.
He never reached Williams’ status, at least not in NASCAR. In a strictly NASCAR assessment, Stewart, 45, falls between fifth and 10th all time. But in a ranking of drivers across a wide variety of disciplines, he jumps toward the top, if not all the way there. He has a well-earned reputation for racing anytime, anywhere. At the bowling alley, Stewart’s then-girlfriend assessed his passion for racing this way: “He’d race you to the bathroom.”
But he didn’t just race every kind of car, he won in every kind of car, too. He has earned 12 series championships. He was the first driver to win USAC’s Triple Crown (championships in three completely different cars in one year), and he is the only driver to win an IndyCar championship and a NASCAR Sprint Cup Series championship. Nobody will ever win that combination of titles again.
But to look at Stewart’s career only based on trophies and titles is to completely and totally miss why his retirement has generated so much talk since he announced it last year. His legacy will be that he was one of the most alternately loved and loathed drivers in the history of NASCAR. I could write a farewell to Stewart piece filled with nothing but praise of his generosity, and it would be 100 percent true. Or I could write a farewell to Stewart piece filled with nothing but vitriol about what a jerk he has been, and it would be 100 percent true.
Stewart has caused controversy for wrecking drivers, feuding with media and mouthing off about NASCAR officials. In 2011, he took his act international when he was detained by police after an altercation with a track owner in Australia. But Stewart also has given away millions of dollars to charity and committed dozens of acts of unseen generosity. He regularly lends out his plane when someone in racing has a crisis and uses his home in Indiana like a boarding house for young drivers.
Racing has gotten expensive to the point where it’s almost impossible for a driver to move up through racing’s lower levels without a famous last name or a dad with an enormous bank account. Stewart had neither. He came from nothing.