The greatest to never win the Daytona 500

(Photo by Jonathan Ferrey/Getty Images for NASCAR)
6 Comments

Life isn’t fair. Neither is the Daytona 500.

For every once-in-a-lifetime moment like Trevor Bayne winning it in only his second career start, there’s a line of NASCAR legends and hall of famers who never experienced celebrating with the Harley J. Earl Trophy trophy.

Dale Earnhardt Sr. was among the latter for two decades. The seven-time Sprint Cup champion had tried 19 times to win the Great American Race.

Then in 1998, Earnhardt celebrated his first and only win in the Daytona 500 like someone who had been runner-up three times and had led at the white flag twice only to see others, including Derrike Cope, take advantage of his misfortune.

Now imagine being Terry Labonte.

When Earnhardt’s No. 3 Chevrolet pulled up lame on the final lap of the 1990 edition of the race with a flat tire, it was Labonte who fell into place behind Cope to finish second as Cope claimed the first of only two Sprint Cup victories. Ever.

Labonte, or the “Iceman,” on the other hand was inducted into the NASCAR Hall of Fame earlier this year after a career filled with two Sprint Cup titles (1984, 1996) and 22 wins.

The Hall of Famer’s first and last wins came in the Southern 500, but nowhere in-between did Labonte claim a victory in the Daytona 500 in his 31 starts. His only NASCAR win at Daytona came in one of the twin 125 qualifying races in 1989.

Like Earnhardt, Labonte was a runner-up in the Daytona 500 three times. The first came in 1986 and the last in 1997 when Hendrick Motorsports swept the top-three spots.

One of the best drivers to never win a Sprint Cup title or a Daytona 50o is Mark Martin.

He was runner-up in the points five times during his 31 years in the Cup series. The closest he came to winning the Daytona 500 also happens to be one of the closest finishes in NASCAR history. While driving the No. 01 Army Chevrolet, Martin led 26 laps in the 2007 Daytona 500.

Martin’s bid came up .02 seconds short as Kevin Harvick won his first and so far only “500” in his sixth start.

Another contemporary of Labonte and Martin who never found Daytona 500 glory is Rusty Wallace. The 2013 Hall of Fame inductee earned 55 Sprint Cup wins and the 1989 championship, but his best Daytona 500 finish was third in 2001.

Wallace’s only win at Daytona was in the 1998 Bud Shootout (now the Sprint Unlimited).

Before being injured driving an off-road vehicle in sand dunes, much of the off-season talk revolved around Tony Stewart and his quest to finally win the Daytona 500 before he retired at the end of 2016.

The three-time champion has won at the 2.5-mile track 10 times in points races, qualifying races and the Sprint Unlimited.

But after 17 starts in the Daytona 500, the best result Stewart has come away with is a runner-up finish in 2004 to Earnhardt Jr. after leading 98 laps.

Also in the conversation of the best active drivers not to win the first race of the year are Kurt and Kyle Busch. The brothers, both Sprint Cup champions, have combined for 24 starts in the “500” but have come up empty. Like Labonte and Earnhardt, Kurt Busch has been the runner-up three times (2003, 2005, 2008).

Kyle Busch, a two-time qualifying race winner and 2012 Sprint Unlimited winner, came closest in 2008 when he finished fourth after leading a race high 86 laps.

The winner that year? Ryan Newman in the only restrictor plate victory of his NASCAR career, in either points or non-points races.

The Daytona 500 doesn’t play favorites.