"When you've won everything but the 500, it's hard to have that confidence that you know how to win the 500," says
That elusive first victory will be Stewart's mission on Sunday and would be his greatest single-day achievement. His hefty portfolio includes wins in two major series -- three in IndyCar and 37 in Sprint Cup -- and championships in IndyCar (1997) and Cup (2002, 2005), but none in either series' most prestigious race. Stewart drove in the Indianapolis 500 five times before abandoning it to concentrate full time on his Cup career. And though he has 13 victories on Daytona's 2.5-mile oval, he has come up empty in 11 Daytona 500 starts.
Stewart has three Cup wins in the early July race, including last year, along with three in the Budweiser Shootout and three in the Duel qualifying races in the cooler conditions of February. He finished second on Thursday to
"We've struggled with getting the car to handle since we've been here, for some reason," Stewart said. "I don't know what's so different this time around, but we go from winning the race back in July to where we can't even make our car turn. So, we're still working on it. But the great thing about this place is that it's about handling. It's been so frustrating running at Daytona for so many years and having to worry about who was helping you [in the draft]. You still need to have help, but if you don't have a good-handling car, I don't care who's pushing you, it's not going to matter."
Stewart has been a contender, running in the lead pack, in six of the past seven 500s at the checkered flag. In 2007, he was leading with 50 laps to go when
"It's pretty tough to say that I'm happy to go from first to third on the last lap of the Daytona 500," Stewart said. "I just made the wrong decision on the backstretch and tried to go down in front of Kyle. I thought we could get a push down there, but the No. 2 [Kurt Busch] got glued to the No. 12 [Newman].
"I don't know if I could've stopped them anyway, and if I would've changed lanes, I think I would've ended up like a bunch of other guys -- wrecked. In all reality and in hindsight, I'm probably going to be a lot happier about it tomorrow. It's hard to explain. It's probably one of the most disappointing moments of my career."
Stewart's career at Daytona has gone down the same track as
This will be Stewart's second Daytona 500 driving for the team he co-owns and runs: Stewart-Haas Racing. He finished eighth in last year's rain-shortened race.
"I've never come to Daytona for the 500 and felt like I didn't have good enough stuff to win, ever," Stewart said. "I didn't always do a good enough job to do it."
Just as it was with Earnhardt and Waltrip, it seems inevitable that Stewart will add a Daytona 500 win to his legacy. It's a very real possibility that it could happen Sunday.