From 1979 to 1997, there was perhaps no driver better at getting to the front of the Daytona 500 than Dale Earnhardt.
The only problem? At the end of 500 miles, he never crossed the start-finish line in first place.
In 1986, the 28th running of the Great American Race played out as if Martin Scorsese was behind CBS’ cameras. In the mid-1980s, Earnhardt’s rivalry with Chemung, New York, native Geoff Bodine made headlines on a weekly basis. In the closing laps, it was Earnhardt and Bodine battling for the sport’s biggest prize.
In what turned out to be a precursor for future heartbreaks, Earnhardt ran out of gas with three laps remaining. While Earnhardt’s No. 3 quietly inched down pit road, his biggest rival at the time in Bodine took the victory.
In 1990, Earnhardt was on the losing end of one of the most heartbreaking losses in NASCAR history. In a race that kicked off a five-year stretch in which Earnhardt won four Winston Cup championships and 24 races, the black No. 3 was by far the fastest car in Daytona Beach.
As Earnhardt entered turn three on the final lap, though, the right-front tire on his Chevrolet went down, handing Derrike Cope the first victory of his Winston Cup career. A fourth-place finish and a blown tire were all Earnhardt and the No. 3 team had to show on a day where they led 155 of 200 laps.
In 1993, Earnhardt was on the losing end of the infamous “Dale and Dale Show,” watching as Dale Jarrett took the win. In 1997, Earnhardt tumbled down the backstretch after a crash late in the race. In true Earnhardt fashion, he finished the race in a car that was ready for the dumpster.
But when the Winston Cup field cranked up their engines on Feb. 15, 1998, there was a different feeling in the air. Earnhardt’s Monte Carlo had a lucky penny affixed to the dash, a product of a young fan in the garage area wanting to give her favorite driver a good luck charm earlier in the week.
And, as NASCAR’s biggest race had played out plenty of times before, it was Earnhardt leading in the closing stages. Instead of Bodine or Jarrett leading the snarling pack behind him, however, Bobby Labonte and Jeremy Mayfield filled up his rearview mirror.
As the laps ticked off, Mayfield and Labonte made countless attempts to get around Earnhardt, each as fruitless as the last.
Not being able to get around Earnhardt at Daytona was normal. All that was left for Labonte and Mayfield to do now was to wait for the inevitable heartbreak to occur. Earnhardt fans across the country waited with bated breath to see what cruel punishment would be inflicted against their driver this time.
With two laps to go, Earnhardt’s No. 3 continued to hold serve over Labonte. As the leaders entered turn three — the site of Earnhardt’s most heartbreaking Daytona defeat — the yellow flag waved for an incident involving Lake Speed and John Andretti.
After using the lapped No. 75 car of Rick Mast as a buffer to ward off any last-ditch effort from Labonte, Earnhardt flew under the white flag, coasting around to take the checkered a lap later.
The words uttered by CBS lap-by-lap announcer Mike Joy perfectly encapsulated the emotion felt by a triumphant Earnhardt.
“20 years of trying, 20 years of frustration! Dale Earnhardt will come to the caution flag to win the Daytona 500!”
Nearly 27 years later, those words remain the most chilling in NASCAR history.
