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Dale Earnhardt vs. Daytona: A long and winding road

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Parker Kligerman celebrates NASCAR's upcoming 75th anniversary season with a historical look at two of the sport's iconic tracks - Daytona International Speedway and Talladega Superspeedway.

It was late in the evening of Feb. 15, 1998, and Danny “Chocolate” Myers was rolling north on Interstate 95, several hours after the Daytona 500 checkered flag.

Myers was on the way to North Carolina, but it had been a long day, one that started in the pre-dawn hours. By the time he reached Jacksonville, it was clear to him that he needed to get a room for the night and finish the trip the next day.

“I stopped at a Holiday Inn,” said Myers, “and walked in and said, ‘M’am, do you have any rooms?’ She said yes. She was the first person that I saw that day who was not at the racetrack, and I said, ‘We just won the Daytona 500.’ She was the first person I was able to tell that to.”

It was no ordinary message.

It was one Myers had waited to deliver for years, and one Dale Earnhardt, who drove the No. 3 Chevrolet that Myers fueled on an almost weekly basis, finally could say after two decades of misery and disappointment in the Daytona 500, NASCAR’s marquee race.

Earlier in the day, Earnhardt had taken the 500 checkered flag first to end a 20-year odyssey. He was the top talent of his generation, built a fan base of historic proportions and won virtually every other race of importance at Daytona International Speedway, but he had not been able to close out the Daytona 500.

On that February day, he did, and the celebrations afterward were legendary. Victory Lane was awash in high-fives, hugs and champagne. Fans lingered for hours after the checkered flag to soak in the moments. Arguably, it was the peak of Earnhardt’s long and prosperous career.

Earnhardt had experienced frustrating losses in the 500. He led on the last lap in 1990 only to have a tire on his Chevrolet explode in the third turn, allowing upstart Derrike Cope to slide past and win. Three years later, he had the lead at the white flag but was outrun by the “other” Dale – Jarrett – for the win.

Across the years, Earnhardt was a reliable winner at Daytona in everything except the 500 – qualifying races, Xfinity races, International Race of Champions events, the Clash, the summer Cup race.

That record, Myers told NBC Sports, made the failures in the 500 less of a lingering issue.

“We had done everything you could possibly do at Daytona except win the Daytona 500,” he said. “I think that would have been very, very disappointing if we hadn’t had all the success we had. Our group was pretty damn tough when it came to losing. We acted like it didn’t bother us, that we’d get them next year. We didn’t hang our heads down. We just went about our business, loaded up and went on and hopefully the next year was going to be better, and finally it was.”

Dale Earnhardt

DAYTONA BEACH, FL - FEBRUARY 15, 1998: NASCAR’s 50th year got off to a bang with Dale Earnhardt winning the Daytona 500 after 20 tries. The win came 50 years to the day of the running of NASCAR’s first race. (Photo by ISC Archives/CQ-Roll Call Group via Getty Images)

ISC Archives/CQ-Roll Call Group

It wasn’t until Earnhardt solved the 500 dilemma that the team realized how meaningful it was to win that race, Myers said.

“We were in the racing business,” he said. “We won a lot of races. We lost a lot of races. Not winning the 500 wasn’t that big a deal until we did win it. Then you realize how big a deal it is.”

Cup teams typically spend much of the offseason fine-tuning their Daytona 500 cars. No detail is too small, no part too minor.

Friends say Earnhardt was obsessed with the black No. 3 entries that would carry his hopes in the season’s biggest race. In January, he would fly by helicopter from his shop in Mooresville, N.C. to Richard Childress Racing in Welcome, N.C. – a 50-mile drive by car – to check the progress on his Daytona car.

“Daytona was another place on the schedule, but it was really important to get off to a good start,” Don Hawk, who was president of Dale Earnhardt, Inc. in the 1990s, told NBC Sports. “Dale raced to win championships. We’d start helicoptering to the Childress shop in early January to check on the Daytona car. He’d say, ‘I want to go see my car.’ He had a keen interest in his car leading up to SpeedWeeks.”

Dale Earnhardt

DAYTONA BEACH, FL - FEBRUARY 15, 1998: Crew members along pit road congratulate Dale Earnhardt following his victory in the Daytona 500 at Daytona International Speedway. (Photo by ISC Images & Archives via Getty Images)

ISC Archives/CQ-Roll Call Group

Typically, Hawk said, Earnhardt was more focused on the intricacies of car preparation at Daytona than at other tracks.

“He was very visible in the garage at Daytona,” Hawk said. “He was always looking at the angles on his car. He was looking at what we might be missing. He stood on the top of the hauler and watched other people practice. He used to live up on top of that trailer.”

Earnhardt was “a different person” after the 1998 win, Hawk said. “He was the most relieved I saw him in my entire life,” he said. “And I’d seen him in a lot of unbelievable situations. That was the biggest weight off his shoulders.”

Three years later, in a grim irony, Earnhardt would be killed on the last lap of the 500, the race that had brought him such sorrow and – on one golden day – such joy.