“I saw three or four clips of races where I remember we had a shot and let it get away from us,” he said. “Everything has to go right. The Indy 500 is the same way. It's easy to compare those two because everything has to go right that whole day.
“You don't normally get the opportunity to have a mistake and come back from it. It just seems like it's hard to make up from a mistake. You look at the guys that normally have that trophy at the end of the day, they're guys that had no drama at all during their race.”
Stewart's best shot at the Daytona 500 was probably 2008, when he was leading with a half lap remaining. He went low to hook up with then-teammate Kyle Busch, and Kurt Busch pushed Newman into the lead and to the win. In 2002, Stewart was dominant in everything through Speedweeks, only to have an engine failure two laps into the Daytona 500.
Greg Zipadelli, who was crew chief for Stewart 10 years, believes the duo had multiple shots to win the Daytona 500 and other big races that have eluded Smoke.
“I honestly can sit here and say that four or five of 10 years together, we shoulda, coulda won the Daytona 500,” Zipadelli said. “We did all we could do at that time, we put an awful lot of effort into our speedway cars … we led a lot of laps, and had some crazy wrecks and some half-a-lap to go passes. Just crazy things.”
Stewart believes luck is just as important as skill and car setup when it comes to the big races.
“You do everything in your power to take care of the science or technology side, do everything you can to build the fastest car you've got,” he said. “Then if you don't have the luck to go with it — even if you don't have any drama with getting the car touched, nothing happens to the car, if you're just in the wrong spot at the wrong time at the end, it can take you out of the opportunity to (win).”
Zipadelli said the duo has taken some solace in their two Brickyard 400 wins at Indianapolis Motor Speedway, but the big losses still sting. Stewart had a shot at winning the Coca-Cola 600 in 2007 until a late flat tire dropped him to sixth.
Stewart can't dwell on it, said Zipadelli, who is now the competition director at SHR.
“I think the worst thing you can do is look at it and put extra pressure on yourself to try and make something happen because that's usually when it doesn't,” he said. “You've got to roll with it and put your effort in and hopefully you are blessed that day.”
Easier said than done, especially this Sunday. Stewart knows that from all his years racing at Daytona and Indy.
“Those two races, the drama that's involved in those two, the pressure that you put on yourself, I've never had any other race like it,” he said. “Not any championship race or anything. If you go to Daytona and Indy, there's just something about running those two races that you don't get anywhere else. You don't have that emotion. That's part of the equation that doesn't get factored into the other races because it just doesn't exist like it does here and Indy.”