On February 18, 2001, Darrell Waltrip stood in the FOX Sports broadcast booth, calling his very first Daytona 500 as a commentator. But this wasn’t just any race, as the three-time Cup Series champion couldn’t hold back his excitement. His younger brother, Michael Waltrip, had just pulled off what once seemed impossible—he won the Daytona 500. “Michael Waltrip is going to win the Daytona 500!” Darrell shouted, his voice cracking with pride.

For Michael, it was the culmination of a long, grinding journey. The win wasn’t just big, it was career-defining. After 462 Cup Series starts without a single victory, he didn’t just win a race, but he won the biggest race in the sport. Victory Lane was filled with champagne, confetti, and his beaming family. It was a celebration he had dreamed of for decades. Michael Waltrip had arrived, and no one could take that away from him. At least, not at that moment.

But the celebration was short-lived. Just moments after taking the checkered flag, news spread that Dale Earnhardt, his car owner and close friend, had crashed in the final corner and sustained a basilar skull fracture that turned out to be fatal. Earnhardt’s death stunned the racing world—and cast a deep shadow over Michael’s greatest professional high. Now, years later, Waltrip opens up about that bittersweet moment that still gives him chills.

Michael Waltrip carved out a career in NASCAR through persistence and passion. Growing up in Owensboro, Kentucky, in the shadow of his Hall of Fame brother Darrell Waltrip, Michael didn’t jump straight into the NASCAR spotlight. He started out working in the family auto body shop, learning the mechanics of racing before ever stepping onto a track. He began competing in the Busch Series in the mid-1980s, slowly climbing the ranks while battling the “Darrell’s little brother” label.

But in 2001, driving the No. 15 Chevrolet for Dale Earnhardt Inc., he rewrote the story in his first race with the DEI team. In an exclusive conversation with Essentially Sports, Michael spoke about the iconic moment. “The Daytona 500 is the biggest race in NASCAR and one of the biggest races in the world. So, to be able to cross the start-finish line and know that you’ve accomplished something that is historic and will live forever was something that was really special to me,” he said.

That was a truly historic win for a driver who thrived in the topmost series for the last 16 years. He had been fighting for it, and after multiple heartbreaks, he finally achieved something. Michael was beaming as his closest friend Dale Sr.’s promise worked. The seven-time Cup Series champion had told him to join DEI to win a race. “You’d win if you drove for me,” he revealed later. And once Waltrip joined Dale Earnhardt Inc., that prediction came true—on the very first try.

But fate had something else planned. As Michael celebrated his win in the victory lane, his friend and team owner, Dale Sr, suffered a tragic crash that took his life. “Best day and the worst day all rolled into one. I believe that we are all on Earth for a certain amount of days, and when it’s your turn to leave Earth, you leave. And that helps me deal with it and helps me to look forward to the day that I leave this Earth and go to Heaven and see some of my favorite people,” he told Essentially Sports, reflecting on the heartbreaking moment.

It was indeed heartbreaking. The Intimidator, who handpicked Michael for that seat, was not there to celebrate his win. The bond between Michael and Dale was built on years of quiet respect. It started with a rivalry not of their own. Dale and Darrell Waltrip were fierce competitors in their day, leaving Michael as a wildcard. In 1988, when Michael was looking for a run in the Busch series, Dale helped him, which started their friendship journey.

Speaking about the picture of him with the same car, Michael Waltrip said, “I think Dale [Earnhardt] wanted to help me, maybe because they were… rivals and Darrel [Waltrip] didn’t, so Dale said, I will… That was the beginning of a lot of good times for me and Dale. From on the track to on the boat in the Bahamas, on his farm in North Carolina, just a real friendship that was basically blossoming.”

That bond made Dale’s absence in Victory Lane all the more painful. He thought Dale Sr. was doing his job behind him on the track. But that job cost Earnhardt his life. As Waltrip stood on the podium, the man who helped him finally reach it was gone. The moment became a mix of triumph and tragedy—a win he could never truly celebrate. Just months later, Waltrip found himself in the middle of another emotional Daytona moment—this time, for someone else.

Michael Waltrip helps Dale Jr. register an emotional Daytona win!

Dale Earnhardt Sr.’s death was something NASCAR found incredibly hard to move on from. As the Cup Series strutted to Rockingham the week following Daytona, gloomy clouds were hanging over the sport. Quite literally and figuratively. Rockingham skies were closed on that Sunday, and Dale Jr. took to the tracks for the first time in his life without his father by his side. It was a move he later admits he was not ready to do. Dale Jr. was not in the headspace to drive that car, and to everyone’s shock, he crashed in Lap 1 of the race, in eerily similar fashion to his dad. Junior walked out fine, and the world breathed a collective sigh of relief.

Ahead of the 2025 Daytona 500, Dale Jr. opened up about his connection with the track as his JR Motorsports team made its Cup Series debut. “When he passed away, I had to make a decision… I knew it wasn’t the track that took him. And I knew that wherever he is, he still felt the same about Daytona. And so, I’ve embraced it. Him losing his life in this property brought this property closer to me.” This decision was reflected in 2001, when the Cup Series made its annual return to Daytona, and Dale Jr. seized the opportunity.

On July 7, 2001, NASCAR returned to Daytona International Speedway for the Pepsi 400, the first race at the track since Dale Earnhardt’s death. The entire sport held its breath. The pressure on Dale Earnhardt Jr. was immense. It wasn’t just another race—it was a tribute to his father’s 34 victories on the iconic track. The weekend didn’t start well for DEI, as all three of their cars qualified outside the top 10.

However, Dale Jr. raced like a man possessed. He led 116 of 160 laps. In the final moments, as the laps ticked down under a late caution, he made a daring move, slicing through traffic to take the lead with just over a lap and a half to go. Behind him, Michael Waltrip was there, just as Dale Sr. had been five months earlier. Waltrip played his role to perfection. He slipped past Bobby Labonte and stayed glued to the back bumper of Earnhardt Jr.’s No. 8 car. He blocked, protected, and ensured no one could get close.

As Junior crossed the line, Waltrip followed in second. The celebration that followed was raw and emotional. Junior spun his car in smoky doughnuts, then climbed on the hood and pointed to the heavens. Waltrip rushed to his side, and the entire Dale Earnhardt Inc. crew flooded the infield. It was a moment that healed a broken sport.

Speaking about the help, Dale Jr. said, “I knew he would help. All I needed was someone to stay behind me.” And Waltrip did, just like Dale Sr. would have. The win wasn’t just for Junior. It was for Dale. For DEI. For the fans. And for Michael Waltrip, who finally got to play the role of protector, just like his friend once did for him.