Race Weekend Central

Bowles-Eye View: Tony Stewart’s Daytona Near Misses Inching Him Ever Closer to Earnhardt

As Tony Stewart sulked Sunday at Daytona – wondering when and how his latest opportunity slipped away – I could only help but think of his connection to a legend.

That connection, to me, is more palpable than ever now.

Perhaps it was because of the historical nature of the day; that as the notes reached a crescendo at the end of the Brooks & Dunn concert, the black No. 3 car Dale Earnhardt drove to victory lane in 1998 was revealed – surrounded by an adoring crowd which stood in awe of the spirit before them.

No doubt, the presence of Earnhardt within the context of Daytona history brought back memories; it appeared even Dale Earnhardt Jr. was choked up after the FOX television crew reminisced about the victory the Intimidator achieved after 19 years of trying, the one which cemented his legendary status within a sport he once dominated.

But as Stewart comes to terms with another disappointment, you have to wonder if he’s on his way to matching that hapless 0-for achievement. The man best compared to the Intimidator by the way he conducts himself on and off the track has done his best to work his way up onto the sport’s biggest stage; but in the end, Stewart’s continued absence from the winner’s list is now clearly defined with the late legend whose pain he shares – and whose list of failures are becoming agonizingly similar.

Strapping in for his 10th attempt at the trophy, Stewart had every right to believe Sunday was going to be his day. Toyotas had been stout all week long, and Stewart had done his part to lead the pack; he finished second to teammate Denny Hamlin in his Gatorade Duel, then went out and won the Nationwide Series race with ease two days later. It’s the third time in four years he’s won the undercard to Sunday’s main event, a sizable total that fits well alongside his three victories in the exhibition Bud Shootout, two Duel wins and even a pair of triumphs in the 400-mile Cup race in July.

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But the key to the 500 is to be around for those last 100 miles, a cold reality that came to Stewart courtesy of a wreck while going for the lead with 47 laps remaining last February. So he decided to take this year’s version in stride; for the better part of 400 miles, he let teammate Kyle Busch hold the baton. Busch led 86 laps while Stewart hung around about fifth through 15th, riding around until it was time to cash in his poker hand with his newly minted Toyota Camry.

And as the laps wound down, it looked like Stewart was holding the royal flush. He hooked up with Earnhardt Jr. and started charging to the front; and when Casey Mears cut right in front of Stewart, the wreck that should have ended his day left his car spotless – while Mears spun hard into the outside wall, nothing really hit the No. 20. It’s the type of luck you need to get on the good side of victory lane here; finally, the growing monkey appeared ready to get off Stewart’s back.

In position to win, Stewart aced the race’s final restart with three laps left; charging forward to first place, he had only the Penske duo of Ryan Newman and Kurt Busch behind him heading to the white flag. Newman, an Indiana native and good friend, had also helped get the No. 20 car to the front over the race’s final stages; surely, Stewart would block, Newman would halt, and hold on similar to the way Jimmie Johnson held off friend Mears in 2006 – right? Right?

By the back straightaway of the white-flag lap, that question was answered in the form of two blue Dodges blasting by Stewart like he was stopped.

“I just made the wrong decision on the backstretch and tried to get down in front of Kyle [Busch],” said Stewart, fresh from watching his win slip away. “I thought we could get a push down there, but the No. 2 (Kurt Busch) got glued to the No. 12 (Ryan Newman). I don’t know if I could have stopped them anyway, and if I would have changed lanes I think I would have ended up like a bunch of other guys – wrecked.”

Of course, that’s where Stewart ended up last year with a car that led 35 laps and appeared to be biding its time behind Kurt Busch. Consider this added to a litany of 500 disappointments that includes:

  • 1999: Stewart captures the outside pole in his Daytona debut, but a mechanical problem sends him behind the wall in a precursor of luck to come. He finishes 28th.
  • 2001: Getting involved in a savage wreck with 27 laps left, Stewart’s car flips end over end in what was easily one of the hardest impacts of his 10-year career. He finishes 36th.
  • 2003: Possesses one of the few cars capable of challenging Michael Waltrip up front before rain at Daytona shortens the day and leaves Stewart languishing in seventh.
  • 2004: Leading a race high 97 laps, Stewart is passed in the closing stages by prodigal son Earnhardt Jr. when the two had long pulled away from everyone else in the pack. He settles for second.
  • 2005: Leading the most laps for a second straight year – 107 – and running up front with seven laps left before losing the lead to drafting buddy Junior once again; eventually, he would lose the race to Jeff Gordon and wind up seventh.
  • 2006: Leading 20 of the first 47 laps, Stewart initially looks like the car to beat, but slowly fades a bit over the race’s second half and winds up fifth by the checkered flag.

Add in the wreck last season and this last-lap snafu, and that brings us to the here and now. It’s a remarkably similar set of circumstances comparable to Earnhardt’s list of oh-so-close; and while he may have lost his wins on the last lap in more hair-raising fashion (see: 1990 tire, turn 3, Derrike Cope), he never lost his confidence that he could eventually win here, a personality trait similar to what Stewart has enveloped. I mean, the man was so confident he offered for any one of us media to come cut his rapidly growing hairdo if he came home with the trophy Sunday night.

Instead, the only scissor-cutting going on was tearing Stewart’s dream in half.

“It’s probably one of the most disappointing moments of my racing career tonight,” he lamented, watching helplessly as Newman stood beaming in Gatorade Victory Lane 100 feet away.

In all, Stewart has led 258 of the last 1,000 laps held for the 500 (five years); that’s easily tops on the list, and is the stuff legends are made of. But for whatever reason, Stewart hasn’t reached that stage of legends quite yet; and for a man who’s won everything there is to win, that reality is more difficult to swallow each time around.

“It’s pretty tough to come in here and say that I’m happy to go from first to third on the last lap of the Daytona 500,” he exclaimed.

It’s even harder when you come to realize it happens every year, on a day when the best of the best congregated to celebrate their place in the sport; and, despite all his accomplishments, Stewart can’t claim that title.


About the author

The author of Did You Notice? (Wednesdays) Tom spends his time overseeing Frontstretch’s 40+ staff members as its majority owner and Editor-in-Chief. Based outside Philadelphia, Bowles is a two-time Emmy winner in NASCAR television and has worked in racing production with FOX, TNT, and ESPN while appearing on-air for SIRIUS XM Radio and FOX Sports 1's former show, the Crowd Goes Wild. He most recently consulted with SRX Racing, helping manage cutting-edge technology and graphics that appeared on their CBS broadcasts during 2021 and 2022.

You can find Tom’s writing here, at CBSSports.com and Athlonsports.com, where he’s been an editorial consultant for the annual racing magazine for 15 years.

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