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Like past greats, Daytona 500 vexes Tony Stewart

Cain: Just as Earnhardt did before him, 'Smoke' wonders if this is the year

Play: NASCAR Fantasy Live

During the mid-1990s, it was almost a Daytona 500 rite of passage.

Long before there were formal organized Media Days, sometime between pole qualifying day and the qualifying races the great Dale Earnhardt would saunter into the cramped and dated old Daytona International Speedway media center, bust a few chops and pat a couple reporters on the back as he navigated the tight quarters to take a seat -- often in a folding metal chair in the corner, summoning reporters to come over to him instead of vice versa.

Sunglasses on, he'd lean back in his chair and, depending on his mood, smile or grimace. Sometimes he waited to be asked the perennial question: "When are you going to win the Daytona 500?" Other times he just cut to the chase himself.

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Some years he was philosophical, other times frustrated, always he was hopeful. He'd won every single other race at NASCAR's iconic track -- most of them multiple times including a mind-boggling 10 straight qualifying races (now known as the Budweiser Duels).

Although Earnhardt clearly came to both expect and dread answering questions on why he, a seven-time champion and the sport's greatest active driver, hadn't won the sport's greatest race, he always acted like each year was going to be "the" year.

And finally in 1998 it was. I never saw him more genuinely happy and exuberant -- The "Intimidator" sporting a grin so wide it seemed like his mustache might touch his earlobes.

Twenty years later, it's a similar scene with another beloved champion, Tony Stewart. As Earnhardt did, Stewart has taught school on the Daytona high banks, hoisting trophies from sports car races to IROC races; after Daytona 500 qualifiers and summer night 400-milers.

And like Earnhardt, it's obvious that the questions of whether he will ever win NASCAR's big one have understandably gotten stale and annoying to Stewart.

The two greats -- one an inaugural NASCAR Hall of Fame member, the other a sure first-ballot Hall of Famer -- are shining examples of one of the sport's most mystifying quagmires.

It took Earnhardt, a seven-time Cup champion, 20 years of trying before he won the Daytona 500. In the meantime, Derrike Cope (1990) and Sterling Marlin (1994-95) scored their first career series wins in the Great American Race.

Michael Waltrip notched his first Cup trophy in the 2001 Daytona 500 after more than 460 starts. And 20-year-old Trevor Bayne scored his first and only Cup win in the 2011 500.

Yet former series champions Rusty Wallace -- a NASCAR Hall of Famer -- along with champion brothers Terry Labonte and Bobby Labonte are a combined 0-for-77 in the Daytona 500. Mark Martin, one of the sport's most successful drivers, is 0-for-29 in the race.

And for the most part, these greats don't even have a lot of near-misses to ponder. Wallace's best finish was third in 2001. Martin won the pole in 2010, had a dramatic runner-up showing in 2007 and a third-place finish in 1995. Terry Labonte has a pair of second-place finishes a decade apart in 1986 and 1997. Bobby Labonte had a sole runner-up in 1998, one of only three top-10 finishes in 22 starts.

As he has become accustomed to in recent years, Stewart -- mostly -- patiently answered the Daytona 500 questions again this month. He joked that he was willing to sacrifice a body part to celebrate in NASCAR's most iconic Victory Lane. He's analyzed and Monday morning quarterbacked the late lap moves that shoulda-woulda landed him there.

Until Stewart finally kisses that Harley J. Earl trophy, his quest to win the Daytona 500 will be one of the most interesting and compelling subplots of the sport's biggest race.

But his success in the 500 is not what defines Stewart as one of NASCAR's greatest champions. Instead, it's the dogged pursuit of that dream that inspires and captivates. Every year, win or lose.

And as Earnhardt did each February for two decades, Stewart has every reason to believe that this is his year.

"Not until the day that I don't run here anymore,'' Stewart said of abandoning hope of a Daytona 500 win. "Everybody has got a shot here, so it's just a matter of ‑‑ we've been in that position before. …  At least that gives you confidence that you've got a shot.

"If anybody looks at my career and says because I haven't won a Daytona 500 that I didn't have a good career, I'd want to say they really don't know what they're talking about."

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