Becoming owner/driver of a Sprint Cup team was exponentially more risky, though Stewart approached it with the same calculation. And to this point, success.
Still, sitting under a portrait of an ebullient -- or medicated --
"The reality of it is, I think we exceeded what anybody thought we could do," he said. "To me, everything we're doing now is icing on the cake, but it would be nice to have all the icing and the cherry on top and all the great things that go with winning a championship too."
Stewart, who led the points standings for much of the season, is currently sixth after finishing 14th at New Hampshire on Sunday. Newman is seventh in points after finishing 12th. Stewart Haas Racing has slowly solidified from an organization with no expectation of success to one that can contemplate a title with the two-time champion in charge. Some of that can be attributed to new people brought in, some to a change of morale. Stewart won three races and the all-star event this season to change the attitude of a once-moribund shop that had never claimed victory.
"Before we made the [ownership] announcement [in 2008], obviously we went to their shop and there were discussions," Stewart said. "But just watching the atmosphere from before we made the announcement to where it is now, it's the same physical building, but it's a whole different building in there now."
As NASCAR's Chase ramps up toward what may or not be a climactic finish on Nov. 22 at Homestead-Miami Speedway, the IRL's season will culminate at the same track in two weeks with three drivers within a nose piece of a title.
Defending series champion
The race virtually assures another close points finish, a hallmark of the simple system the IRL has employed -- with a few adjustments -- since its formative days in 1996. And it all started with Chitwood auditing a race result.
Chitwood wasn't sure he'd made a prudent decision. He'd grown up riding stunt bikes in his Tampa family's traveling daredevil show, broken away on his own to finish an MBA, and here he was lugging boxes full of medical supplies for this start-up racing circuit at a makeshift track at Walt Disney World in 1996.
"I get hired for three months to help out at Disney World Speedway. I'm carrying TVs, all kinds of stuff," he said. "I'd just graduated with a finance degree. I'm thinking, 'My wife is going to kill me. This is not what I signed up for.'"
The gamble eventually proved worthwhile. The IRL prevailed in the bitter but equally destructive civil war with Champ Car, and Chitwood rose from an administrative head -- "I was in charge of entry blanks, credentials, prize-winning, insurance, everything you didn't have enough of " -- to the presidency of Indianapolis Motor Speedway.
It was more than a name plate on a desk for a man who had "been to every track in the country" as part of his family's show. His grandfather, and namesake, had contested seven Indianapolis 500s from 1940 to '50, finishing fifth three times. He felt a kinship with the place and what was a restoration project for its image and national relevance.
His departure in August -- to become vice president for business operations with International Speedway Corporation -- removes another set of hands that helped hold the fledgling circuit together. But he's left a few things behind, among the most important, the simple, yet fair scoring system that has produced several compelling championship battles in recent years.
And to think it all began when he used his finance degree to work while vetting a USAC points report in the league's second season.
"After the Phoenix race, I'm kind of putting together what the prize money should be and I catch a mistake with the USAC points after the race that no one else caught. And I'm a little bit like, 'What if I do it, and it's wrong, it's going to affect how you pay out prize money'," Chitwood recalled. "So I kind of write out a little memo trying to be politically correct, but basically catch a mistake."
Indy Racing League officials decided to form their own sanctioning body before the 1997 season and Chitwood was tasked with Speedway historian
"So we took the last year and started running some things and came up with 50 to win, 40, 35, 32, then down by a point, and that's how we did it, basically," Chitwood remembered. "But it wasn't like we just did it. We looked at some other models, at what other people were doing and came up with something that seemed to make sense. You have a benefit for winning, but fifth place wasn't a detriment and it seems like it worked out well."
Very well. Since 2006, the eventual champion has won by fewer than 17 points.
All of which greatly pleases IRL president of competition
"It was well thought out, because it balances out the emphasis on winning and it rewards some consistency and it plays out very well," he said. "And I think our points battles over the past several years have certainly validated our points system, and we don't need to do anything to contrive competition or reseed or do anything in terms of artificially trying to create excitement. It's not to say someone can't come in and dominate. They can, but we've been very fortunate the sport has been exciting and on the edge the last couple years, and we've come down to the last race."