“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 Waltrip and Dale Earnhardt Sr. had been friends for years, but driving for his team in the Cup Series? That was a big deal for Waltrip. A driver who built his career brick by brick, fought for every inch on the track, and racing for his friend was everything. And what better way to kick things off than the Daytona 500? Despite qualifying 15th for the race, Waltrip kept the laps coming in. By Lap 167, he was right behind Steve Park, who held the lead. In just a single lap, Park was left behind, and Waltrip was cruising to a win. It was almost the perfect start to his time in the team. Almost.

As he crossed the finish line, Ken Schrader came up to him. As Michael described it, “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.’” Behind him, in the final turn of the final lap, racing legend Dale Earnhardt, The Intimidator, slammed into the wall in a crash that would take his life. The celebration never truly began.

While it changed NASCAR forever, it turned Michael’s world upside down, and it’s a loss he battles even today.

Speaking with Davey Segal, the host of SiriusXM NASCAR, Mike Kelley, the Crew Chief of Michael Waltrip, got emotional reminiscing about the ill-fated day. Davey Segal posted a snippet of the interview on X, writing, “@MkelleyHyak was the car chief for @MW55 in the 2001 Daytona 500 and still gets emotional while remembering that fateful February day. I so appreciate Mike’s openness and reflection. Raw, honest emotion.” As emotions tightened his voice and the weight of the moment hung heavy in the room, Mike Kelley reflected on the great legacy of Dale Earnhardt and how NASCAR will forever be indebted to him.

Dale Earnhardt‘s aggressive style and unrelenting will to win made him one of the most polarizing and admired figures in motorsports. Remembering the day and Dale himself, Kelley remarked how a great day turned into a nightmare rather than a celebratory memory for the team. “It’s still emotional today, all these years later, to come out of there with the win and the 500 is incredible, right? It’s Cinderella story 101, but then to lose Dale on the last lap, you never get to celebrate that win, you just can’t,” Kelly said in the interview. “The garage just shut down and Mike Helton walked over and we closed the hood and we discussed whether there would be a putting it in the Daytona USA the next day and decided that was against that.”

For Waltrip, that win was the culmination of decades of hard work. Back in 1978, when Michael was 12, he called his brother, the Cup Champion Darrell Waltrip, for help. But when his brother asked him to focus on school. That’s when Michael started racing karts, slowly building himself up, living with Richard and Kyle Petty.

And when Michael thinks of that race, he doesn’t think of his first win, but the loss of his friend. “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.” 

The tragedy was huge; the raw grief and confusion of that night lingered in the mind of every American, leaving a permanent scar in NASCAR’s history. “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,” Kelley continued, recalling the support that the crowd has given to the team and to the family.

Earnhardt’s funeral was a solemn and emotional event held on February 22, 2001, attended by family, friends, fellow drivers, and key figures from across the motorsports world, reflecting the immense respect and admiration that the man commanded. When NASCAR finally banded together at Rockingham, a silence hung in the air. Yet, when Steve Park won the race, he raised a No. 3 cap while he did the Polish lap on the front stretch. Fans erupted in suppor,t and even Michael joined in, high-fiving his teammate.

Kelly capped it off perfectly with his own experience dealing with the tragedy. “I was going through a box, I generally do it during the winter just to kind of revitalize myself and I pulled out my DEI crew uniform and my Daytona 500 crew uniform,” Kelley recounted. “But inside there’s also a black DEI shirt that we all wore to the funeral, and it just reminds you of all that in one day, how big it can be and how low it can be.” On that day, the team hoped that they had experienced the day differently, or if they had fixed the slot, just to see him still alive, but no one could change the past, and it remained a burden on the hearts of many.

Waltrip reveals his doubts about the Rockingham weekend

For Michael Waltrip, the run up to the Rockingham race was a mixed bag.  “In my mind, there was going to be indecision. Do we go to Rockingham? Do we sit it out in honor? And we decided collectively as a group — and certainly correctly — Dale would be pissed if we didn’t go to Rockingham,” Waltrip recalled during an appearance on Kevin Harvick’s Happy Hour.

The race became a tribute to the man who built the foundation for DEI, therefore, they raced in respect for Earnhardt’s legacy, following the footsteps of someone who would never back down.

“So, you know, we went down there, and I just found through God and faith that the reason why I won that Daytona 500 that day is because it wasn’t about me,” said Waltrip. “You know, it was about the team, and it was about Dale giving me this wonderful opportunity. The press conference I thought worked good because I was able to share that story and tell people that I believe that Dale was in a better place, and that’s how I moved forward.”

Through the heartache, they honored the Intimidator by staying in the race.