Everyone knows the Dale Earnhardt story, especially when it comes to the struggles to win the Daytona 500. Note, I did not say struggles at Daytona, but struggles to win the Daytona 500. Earnhardt was not alone. Many of the sport’s top drivers failed to win the Daytona 500, especially of the recent generations. Rusty Wallace, Mark Martin, Bobby Labonte, Kurt Busch, and Ricky Rudd headline the list of top tier drivers in the past 30 years who failed to ever win the Daytona 500. However, where Earnhardt separated himself from those other drivers however was his overwhelming career success.
In fact, the only drivers to join Earnhardt as multiple time series champions to make at least 16 starts in the Daytona 500 without a win are Darrell Waltrip, Terry Labonte, and Tony Stewart.
One of these was often compared to Earnhardt when it came to belaboring their Daytona nightmares.
Labonte, for all his successes at the Cup level, is what I would call the Tim Duncan of NASCAR. Almost nothing he did was noticed. While much was made of Earnhardt and Waltrip’s struggles to win the Daytona 500, it’s almost forgotten that Terry Labonte finished second in the Daytona 500 three different times. You can’t get much closer than that. Perhaps it was that Labonte only led a combined 12 laps in the three races. In fact, only once did Terry Labonte lead double digit laps (1996 when over heating issues relegated him to 24th place) in a single Daytona 500. So despite three runner-ups, and six top five finishes, Labonte, and his “mere” two championships never got quite the same attention when it came to striving for Daytona 500 glory, and as such, never received the sympathy for his failures.
Darrell Waltrip though was a different story. Before there was Earnhardt and his well documented struggles, there was D.W. Waltrip, like Earnhardt, was a multiple time champion (three) who had won everything there was to be won in the sport. Everything, of course, except Daytona. And much like Earnhardt, Waltrip had won just about everything at Daytona….except the Daytona 500. Well, with one exception. While he had won the qualifying race on Thursday five times, finishing second an additional three times, and also claimed victory in the Busch Clash, three of the Saturday Busch Series races (Now Xfinity Series), and an IROC race, Waltrip had never won a points paying Winston Cup race at Daytona. So even he didn’t compare similarly to Dale Earnhardt.
But that doesn’t mean there isn’t someone who does.
Waltrip’s run of futility ended in his seventeenth start, which happens to be the number start Tony Stewart will make in the Daytona 500 when the green flag falls this Sunday.
And when it comes to comparing the Daytona nightmare to Earnhardt, nobody compares quite like Stewart.
Stewart, like Waltrip, is a three-time champion. But as good as Waltrip’s record was at Daytona, Stewart’s is vastly superior. The remarkable thing, is that as superior as Stewart’s is, Earnhardt’s is that much better. But I digress. Stewart has the overall career success, the Daytona success, and like Earnhardt, the supreme Daytona heartbreak riding with him in Sunday’s Daytona 500.
The resume speaks for itself for “Smoke”. He’s won the Sprint Unlimited three different times, finishing second on two other occasions. The Thursday Gatorade duels? Stewart has gone to victory lane three times in those as well, finishing second another five times. In fact, from 2002-2010 Stewart finished worse than second only twice. Stewart however did something Waltrip never did, win on Daytona’s road course, winning an IROC race there, while also adding a win on the traditional 2.5 mile layout in 2002. But where Stewart’s dominance at Daytona most resembled Earnhardt? The Saturday Nationwide Series (now Xfinity Series) race at Daytona. From 2005-2013 Tony Stewart won the race a remarkable seven times in nine years. But the Stewart Daytona 500 resume doesn’t end there. He also won the July Cup race four different times, and added a runner-up. If you’re doing the mat at home, that’s 19 wins at Daytona for Stewart and another eight runner-up finishes in events aside from the Daytona 500. To say he’s dominated this track is an understatement.
But he hasn’t won the Daytona 500.
And he’s been close. He’s been very close. He’s suffered heartbreak in every way imaginable, just like Earnhardt. He’s had the dominant car, he’s lost late leads, and he’s had the race end before it ever even got started.
Stewart qualified on the outside poll for his first Daytona 500 in 1999, but engine failure prevented him from contending for the win. Unfortunately for Stewart, it seemed the trend had been set.
Stewart has led in half of the Daytona 500s he has entered, and on multiple occasions established himself the class of the field.
The 2001 Daytona 500 is known for many things, but perhaps lost in that shuffle was the big accident that Earnhardt narrowly missed, the one that happened with 27 laps to go that resulted with Stewart flipping wildly down the back straightaway.
In 2004 Stewart led almost half the race, for a total of 94 laps, but Dale Earnhardt Jr passed him with twenty laps to go en route to his first Daytona 500 victory.
In 2005 Stewart took it up a notch, leading over half the race, for a total of 107 laps, and held the lead with four laps to go, only to be shuffled back to seventh place by the event’s conclusion.
Two years later, Stewart had established himself, along with Kurt Busch, the clear class of the field. But after leading his 36th lap of the race on lap 152 of 200, Stewart and Busch tangled in turn four with Stewart leading, paving the way for the spectacular Mark Martin/Kevin Harvick finish.
The following season Stewart led the field to the white flag…only to watch Penske teammates Ryan Newman and Kurt Busch draft past him on the final lap.
The Trevor Bayne Cinderella story in 2011 almost wasn’t….. Stewart restarted second on the final green-white-checkered, but a poor restart cost Stewart and he wound up 13th.
But Stewart lady luck didn’t always wait until the final 20 laps to snatch victory from Stewart. In 2002, the first return to the 500 after the wild crash the previous year, Stewart only made it two laps before the engine failed in his Joe Gibbs Racing Pontiac.
So to say Stewart has had it with the Daytona 500 might be an understatement. Considering what Stewart has gone through over the past 18 months, between the broken leg, the poor on track performance, the Kevin Ward tragedy, and now dealing with the Kurt Busch saga, what could be sweeter for Smoke than to finally exorcise those Daytona demons? Waltrip did it in his 17th try, maybe that’s the trick for Stewart too.