Michael Waltrip’s victory at the 2001 Daytona 500 stands as one of NASCAR’s most emotional moments, a career-defining win forever intertwined with the tragic loss of his mentor, Dale Earnhardt Sr.
After 462 winless starts in the Cup Series, Waltrip finally broke through to claim NASCAR’s most prestigious race only to have the triumph instantly overshadowed by the fatal crash of the very man who had given him the opportunity.
The Mentorship That Changed Michael Waltrip
“In my racing career I’ve never experienced the energy and the positivity and the excitement for a season like I had the 2001 season,” Waltrip said. “Dale was my mentor and he was telling me what I needed to think about and do. I’d never had that before.”
Before a big race at Daytona, Waltrip sat in on a meeting where Earnhardt laid out exactly how they were going to win. This was eye-opening for him. “I’m like, holy crap, no wonder I haven’t done very good so far. I haven’t ever had all this before,” he recalled.
With Earnhardt’s belief in him, Waltrip’s confidence grew. “Dale Earnhardt Sr. had told me I had the ability, and that day, I knew I would (win),” Waltrip said.
But what should have been the happiest moment of his career quickly turned tragic. While Waltrip took the checkered flag, Earnhardt crashed on the final lap and didn’t survive. For Waltrip it was a win wrapped in heartbreak; the victory he’d waited so long for was now forever tied to the loss of his mentor.
Just a week later, the NASCAR teams had to race again at Rockingham. Waltrip struggled with whether they should even go. “We decided collectively as a group—and certainly correctly—Dale would be pissed if we didn’t go to Rockingham,” he said.
Being at the track without Earnhardt was incredibly difficult. “Getting in the race car and getting out there, that was hard. That was probably the hardest part for me. Not the press conference, but just going to work. That should be what your escape is… But that weekend—it was just hard. I didn’t really feel like being there.”
Years later, Waltrip still honors his friend and mentor. He recently shared a photo of them fishing together on X with the simple caption “Miss you friend. #For3ver.”
For Waltrip, what made the difference in his career wasn’t just having better equipment or opportunities; it was having someone who believed in him and showed him the way. After years of trying to figure it out on his own, he finally had the guidance he needed from Earnhardt, something he “never had” before.
