What was supposed to be the best day of Michael Waltrip’s life became the worst. On the day Waltrip won his first-ever NASCAR Cup Series race at the Daytona 500, the motorsports world reeled from the loss of his boss and mentor, Dale Earnhardt.
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As the #15 Dale Earnhardt Inc. driver was crossing the finish line for the first time as a victor, Earnhardt was involved in a fatal collision in Turn 4 at Daytona International Speedway, making contact with Ken Schrader, before crashing into the outer wall.
Emergency response teams were on the scene immediately, but it was confirmed at a nearby hospital that Earnhardt had succumbed instantly to a basilar skull fracture, a catastrophic injury caused by the rapid forward motion of his head upon impact.
Waltrip, who had been competing in the NASCAR Cup since 1985, had awaited victory for 17 years and 462 races. His long-awaited win was overshadowed by the absence of his team owner, turning a moment of success into sorrow.
Fans recently revisited the moment in a thread sparked by a heartfelt post on Waltrip highlighting his struggle, where a NASCAR enthusiast reflected, “Dale was the only one that believed in him. Dale not being able to see him succeed is brutal. Michael saying that we was looking around, waiting for him to come to victory lane, but he never came…. tears. every. time.”
After the race, Waltrip knew only that Earnhardt had crashed; the gravity of the situation was unknown to him as he lingered on the pit road, eagerly anticipating a congratulatory embrace from Dale Sr. that never came. It was nearly an hour later that he was confronted with the devastating news of Earnhardt’s passing.
Amidst the shared reflections, a fan pointed out, “Another thing about that race was Dale chose to defend that day. Dale always went for the win and that day he was racing for his guys. I like to think on that last lap he was damn proud of his drivers sitting 1-2 and he made his car as wide as it had to be to hold the field back.”
Another NASCAR aficionado commented, “Team owner and one of his best friends…talk about best day of your life turned worst day in a hurry. I’ve always felt bad for him because his first win will always be one of the darkest days of his life .”
Waltrip reflected on that fateful day, labeling it as “The worst day of my life. It went from the best day to the worst, just like that… If I could change history or change life, the hug I would have gotten from Dale after the race that day would have been the best hug I’ve ever had in my life.”
After his win at the 2001 Daytona 500, Waltrip continued to find success on the same track, securing a win at the Coke Zero Sugar 400 the following season and another Daytona 500 triumph in 2003, before bagging a win at Talladega. Despite racing full-time in the Cup Series until 2009, Waltrip never crossed the finish line first again after his Talladega win.
