Dale Earnhardt saw something in a notoriously winless NASCAR Cup Series driver that no one else did. It forever altered Michael Waltrip’s career and legacy with a triumph that Earnhardt never lived to see and celebrate.

And it left the motorsports world wondering what might have been had Earnhardt not died that fateful day in the 2001 Daytona 500.

Dale Earnhardt made a bold decision ahead of the 2001 NASCAR season

Dale Earnhardt had long been a mainstay of the Richard Childress Racing team, driving the No. 3 Chevy beginning in 1984. Along the way, however, the legendary driver and his wife formed Dale Earnhardt, Inc., which began running cars in what are now the Xfinity and the NASCAR Cup Series.

Earnhardt had Steve Park driving the No. 1 Chevy and Dale Earnhardt Jr. in the No. 8 Chevy. Following the 2000 season, Earnhardt made the decision to add a third car after first floating the idea with NAPA Auto Parts executives. NAPA agreed to sponsor the team. Given how big Earnhardt’s name was in the sport, it would have been reasonable to expect that DEI would recruit either a successful veteran or a promising young driver to take the wheel.

Instead, Earnhardt made a head-scratcher of a decision by offering the new No. 15 Chevy to Michael Waltrip, who was well-liked in the racing world but possessed a winless streak that was approaching historic proportions.

Waltrip began racing in the NASCAR Cup Series in 1985. Darrell Waltrip had won 84 times in 29 years before retiring after the 2000 season to go into the broadcast booth with Fox Sports. But his little brother had been 0-for-462 while racing for six teams beginning in 1985.

DEI was taking a huge chance with Michael Waltrip.

Dale Earnhardt had an unexpected reaction as Michael Waltrip tried to sneak past him

The Daytona 500 attracts maximum attention in the racing world because NASCAR leads off its seasons with its most prestigious race. The 2012 event further piqued the interest of fans by being the debut of Michael Waltrip with Dale Earnhardt, Inc. The idea of bringing in a 37-year-old driver who was winless in his career was unconventional at best.

Whatever doubts that already existed intensified during Speedweeks. Racing in the 125-mile qualifier, Waltrip missed a shift on the final restart. Suddenly, a potential victory that would have alleviated considerable pressure turned into a ninth-place finish.

In an interview with ESPN a decade later, Waltrip recalled walking from his motor home to the garage the following morning.

“I almost felt like I was trying to tiptoe past Dale’s bus,” Waltrip admitted. “I didn’t want to see him. I didn’t want to talk about it. And it was funny. He stuck his head out the door and came out and yelled at me, ‘Hey! Get over here!’”

Waltrip was sure he was about to get chewed out by his boss, and he launched into a pre-emptive apology.

“I said, ‘Man, I screwed up. I should have won that race yesterday.’ He said, ‘No, you shouldn’t have. I should have.’”

The miscue was literally and figuratively yesterday’s news to Earnhardt. He had already turned his focus to Sunday’s Daytona 500.

“He said, ‘Me and you and Dale Jr. are gonna win it,’” Waltrip said. “’We’re gonna work together.’”

Triumph and tragedy at the 2001 Daytona 500

Even casual race fans know what happened on Feb. 18, 2001. Teamwork amongst Dale Earnhardt, Michael Waltrip, and Dale Earnhardt Jr. succeeded even better than imagined. Earnhardt found himself holding down third place as his son and Waltrip raced toward the checkered flag.

Waltrip broke the 0-for-462 winless streak that had come to define his career. And he did so in the Daytona 500, the biggest race on the NASCAR Cup Series schedule.

It was more than half an hour later, after celebrations with his crew and family, that Waltrip learned that the last-lap crash behind him had collected Dale Earnhardt’s car — and the situation was more serious than initially indicated. TV footage would later show fellow driver Ken Schrader peering into the No. 3 Chevy and immediately pleading for rescue workers to hurry to the scene. However, details remained sparse.

“I remember seeing (Schrader) come into victory lane and I thought, ‘Finally! Here comes somebody I know to say congratulations,’” Waltrip said.

That wasn’t the case, though. Schrader wanted to let Waltrip know that Earnhardt was seriously injured. Minutes later, Waltrip was being taken by van to the press box for the usual batch of interviews for the top finishers. It was there that Buffy Waltrip broke the news to her husband that Earnhardt had died.

“We just hugged each other and cried,” he said. “We were just in disbelief. It was like, ‘How?’”

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