For Michael Waltrip, that 2001 Daytona evening was going to change everything. Having asked his brother Darrell about a NASCAR career when he was 12, Michael was quickly shot down, but he never quit. He was a man on a mission, and he wasn’t going to let anyone stop him. Race after race, Waltrip kept putting in the work but it just didn’t go his way. And when his best friend, Dale Earnhardt, had a solution to his losing streak, Michael jumped at the chance. “When I was racing and losing, he’d always tell me, ‘You’d win if I put you in my car.’ So I said, ‘Put me in one,’” Michael revealed. He had his chance, and he wasn’t going to give it up. A brutal climb up from 15th on the grid, and by Lap 167, he had done it. His teammate and race leader, Steve Park, was in his mirror. But as he crossed the line, the worst news possible hit him. “Kenny Schrader came to victory lane (after the 500) and said, ‘I just want you to know that I saw Dale, and it ain’t – it ain’t good,’” he revealed.
Dale Sr. was gone. Right before he could watch his friend win his first Cup Series race, the Intimidator slammed into the wall in a crash that changed NASCAR forever. It’s a loss Michael feels to this day, especially after watching the Earnhardt documentary.
24 years of bottled grief erupted. Retired at 62, Waltrip lay in bed watching Amazon Prime’s new documentary, Earnhardt. As never-before-seen footage flashed—Earnhardt laughing, plotting races, being “the father and the person and the friend” his children Kelley and Dale Jr. wanted fans to see Waltrip shattered. He took to X, typing raw through tears: “Lying in bed watching #Earnhardt and crying like a baby. Remembering and missing Dale.”
Laying in bed watching #Earnhardt and crying like a baby. Remembering and missing Dale.
— Michael Waltrip (@MW55) May 29, 2025
In 2001, Waltrip’s Daytona 500 victory lane joy turned into horror when Earnhardt never arrived. “I kept looking over my shoulder at the gate… I wanted that hug more than the money or trophy,” he confessed years later. DEI executive Ty Norris finally delivered the news: Earnhardt was gone. “It went from the best day to the worst, just like that,” Waltrip admitted. Days later, at Rockingham, grief was a lead weight: “Getting in the race car… that was hard. That should be your escape… But that weekend, it was just hard. I didn’t really feel like being there.”
It’s a loss that keeps stinging every time we go back to it, and for Michael, it’s a wound that might never heal. Speaking about it back in 2019, Waltrip said, “I lived it and I think about it every day. I wonder so much about ‘what if’ and ‘why.’ It still hurts today (after 18 years) as much as it ever did. There’s no way I could have told the story without getting emotional, but that’s just who I am. People obviously are capable of handling the highest of highs and the lowest of lows. God made us that way. But I don’t know how many people have had to experience them within a few seconds of each other.”
And it was a loss felt across America. Earnhardt was a national icon. As Mike Kelley, Waltrip’s crew chief described it, “People at every gas station, we stopped at every restaurant had no idea who we were, we’re talking about Dale that day… and then trying to get to our shop for the rest of the week to get our Darlington store Rockingham stuff together, and seeing the amount of flowers and in the outpour, and to know that all went down on what should have been a group of ours.”
When it comes to such a big loss, it’s only natural that his friend Waltrip makes a gesture for his friend.
Michael Waltrip’s Tribute Beyond the Track Continued at Rockingham
Remember when we said Waltrip was unsure about the Rockingham weekend right after Dale’s death? Well, there was more. Steve Park, his teammate, dominated the race, but the real kicker came when he won the race. Holding out a No. 3 cap, Park killed the silence that hung in the air as fans roared their approval. Even Waltrip joined in, high-fiving his teammate.
And Michael Waltrip made his own tribute to Dale as NASCAR went back to Rockingham this year. “Going back to the Rock takes me back to fun times with Dale. We loved fishing. Miss you friend. #For3ver,” he wrote on X, sharing a picture of the two friends fishing. It was a memory close to Waltrip.
It was more than a tribute. Dale Sr. did all he could to make his friend’s dream come true, as Ty Norris revealed at the time. “Dale Sr. was just trying to hold everybody else off so the three of them could race for the win at the end. A lot of people have said Dale spent the entire race blocking. It certainly looked that way, but he just wanted to get the end of the last lap where the three of them could compete for the win.”
What do you think of the gesture?
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