Daytona 500: After 19 Years Of Heartbreak, Dale Earnhardt Finally Wins In 1998

Dale Earnhardt NASCAR
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We’re less than a week away from the start of the 2022 NASCAR season.

And with the Daytona 500 in just a few short days, we’re taking some time this week to look back at some of the most memorable moments in the history of the Great American Race.

Yesterday we looked back at the “Dale and Dale show” – the 1993 Daytona 500 battle between Dale Earnhardt and Dale Jarrett that saw Jarrett bring home his first Daytona 500 victory and the first ever NASCAR win for Joe Gibbs racing while his dad called the race from the TV booth.

That was Dale Earnhardt’s 14th attempt at winning NASCAR’s biggest race, and 14 times he had come up short.

But on February 15, 1998, Earnhardt finally managed to take the checkered flag in the Daytona 500.

As the sport geared up for the 40th running of the race, much of the conversation leading up to race day centered on Dale Earnhardt – and mainly on the fact that in 19 previous tries, he hadn’t been able to win the big one.

He had won just about everything else there was to win in NASCAR. Earnhardt was a 7-time champion, and he had three victories each in some of the sport’s other crown jewel races: The Coca Cola 600, the Southern 500, and the Winston All-Star Race. Oh, and he had also won the 1995 Brickyard 400, in only NASCAR’s second visit to the most historic track in all of motorsports, Indianapolis Motor Speedway.

He also had more wins at Daytona International Speedway than any other driver in history, winning the pre-season Busch Clash on six occasions and racking up a staggering 12 wins in the Twin 125s, the qualifying races for the Daytona 500. Add on to that the two times he had won the July race at Daytona and his seven victories in races in the then-Busch Series, and Dale had built quite the resume as one of the greatest racers of all time at Daytona International Speedway.

But for nearly 20 years, the Daytona 500 had eluded him.

It was his white whale – a trophy that he so desperately wanted but that always seemed to slip through his fingers.

The Frustration Was Mounting

Over his previous 19 tries, he had lost the Daytona 500 in almost every way imaginable. There were second place finishes and spectacular crashes. There was the time in 1986 when he ran out of gas with three laps to go, and then blew an engine leaving pit road.

And there was the heartbreaking loss in 1990 when a piece of debris cut down his tire while he was in the lead with less than a lap to go.

Dale was frustrated.

And going into the 1998 Daytona 500, all of the attention was on whether one of NASCAR’s greatest drivers would ever manage to win NASCAR’s biggest race.

Earnhardt qualified in fourth position for the race. And before the race, he gave his crew chief Larry McReynolds some simple directions:

“You just keep me in touch with the lead all day long, and if I’m running second on that last lap, that guy that’s leading, his day’s going to go bad, real fast.”

Earnhardt took the lead on lap 17, and with no cautions during the first 125 laps, it was a remarkably fast race for Daytona.

In fact there were only three cautions in the entire race: The first was for debris after Ward Burton cutting down a tire, and the second came on lap 174 after two cars made contact in turn 2 and spun on the track.

Earnhardt had led since lap 140, and when the second caution flew he led the rest of the field down pit road for service, and managed to come back out on the track at the head of the pack.

It was a familiar place for Earnhardt, to be in the lead in the Daytona 500 late in the race. Seven times before he had been leading the race with 20 laps to go, and four times he had been leading with 10 to go. But he had never been able to seal the deal.

As the cars behind him jockeyed for position, Earnhardt led the field with two to go and a hard-charging Bobby Labonte in his rearview mirror.

The Final Lap

Coming off of turn two headed towards the white flag, a crash behind the leaders brought out a caution flag. (But remember, back in these days, the field didn’t freeze when the yellow came out – they raced back to the caution flag).

All of a sudden, the race to lead this lap became the race to win the Daytona 500. Labonte was fighting hard to get around Dale, but the slow car of Rick Mast was just up ahead of the leaders.

As he pulled up alongside the lapped car of Mast, Earnhardt used him as a pick to hold off the cars behind him from getting to the lead. And coming out of turn four, he jumped out ahead to bring his car to the waving white and yellow flags that would freeze the field for the final lap.

Earnhardt just had to make it one more lap under caution to finally win the Daytona 500. His crew chief, McReynolds, held his breath as his driver made his way around the track one final time.

But as Earnhardt was approaching the checkered flag, McReynolds heard a strange voice on the radio:

“Hey Sunday Money, this is Captain Jack. Why don’t you go out there and snag that big one today?”

McReynolds was furious. Here was his driver, trying to turn one more lap to win the biggest race of his career, and somebody was interrupting him on the team radio.

But as McReynolds got set to key up his microphone and, in his words, “cuss him for everything he’s worth,” team owner Richard Childress got his attention and pointed up the suites above the track.

And that’s when McReynolds realized who was talking to Dale on the radio: It was NASCAR CEO Bill France Jr, calling the sport’s biggest driver to victory in the sport’s biggest race.

Meanwhile on TV, announcer Mike Joy was making the now-famous call that’s probably etched into any Dale Earnhardt fan’s brain:

“20 years of trying, 20 years of frustration, Dale Earnhardt will come to the caution flag to win the Daytona 500! Finally!”

But when Dale brought his iconic #3 GM Goodwrench Chevy under the checkered flag, it wasn’t just Earnhardt and his team that were ready to celebrate the Intimidator: It was the entire garage area.

In a now-iconic scene, as Dale drove his car down pit road and towards Victory Lane, every crew member on every team in the race had lined the pits to congratulate Earnhardt on finally capturing his first Daytona 500 win.

Once he got to Victory Lane, you could see 20 years of frustration fade from Earnhardt as he celebrated:

“This is for all them race fans and all them people that have been saying ‘Dale, this is your year. Dale, this is your year.’ And boy a lot of ’em said it this year…

The Daytona 500 is ours. We won it, we won it, we won it.”

It would end up being Dale’s only victory in the Daytona 500 – and we all know what would happen in that race just three short years later.

But on this day in 1998, after 20 years of heartbreak, Dale Earnhardt finally captured the one trophy that was missing from his collection: The Daytona 500.

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