After 19 Years of Failure, What Made Dale Earnhardt Confident He Could Win the Daytona 500 in 1998

It took Dale Earnhardt Sr. 20 swings at the Daytona 500 before he finally captured the sport’s most elusive prize, and when he ultimately broke through, the celebration was every bit as explosive as the moment itself. Dirty Mo Media recently revisited that landmark moment by posting a clip from a 2021 Dale Jr. Download podcast snippet in which longtime NASCAR analyst Larry McReynolds retraced the win through the eyes of a seasoned crew chief who lived every lap of it.

Dale Sr.’s 1998 Daytona 500 win came after 19 previous tries and finally filled the one glaring gap on his résumé, despite more than 30 prior wins at the Daytona track in other events. The victory came with a then-record payout of over $1 million. He claimed the checkered flag by holding off a late charge and cruising under caution to seal the historic win.

McReynolds recalled that Earnhardt recognized the car’s advantage almost instantly, crediting subtle aerodynamic refinements that allowed him to lead 107 laps and edge Rusty Wallace by 0.668 seconds.

“We talked quite a bit during the offseason. Even though I think we were down, I don’t think either one of us had really lost our confidence. I don’t think we’d lost our confidence in each other… But over the offseason, we still have some energy. We were optimistic,” said McReynolds.

That optimism centered around a single machine they believed would carry them through Speedweeks in 1998. According to McReynolds, they built the car in the summer of 1997, then sent it through repeated wind-tunnel sessions and multiple Talladega tests with Marcus and Mike Dillon before Dale Sr. ever sat in the cockpit.

McReynolds recalled the Intimidator’s reaction during the January Daytona test with crystal clarity, saying he could still picture the grin the first time Earnhardt climbed out. As he put it, “When we went to Daytona, tested that thing in January, I can still see Cheshire Cat grin the first time he drove it. He said this thing’s good.”

Senior’s list of near-misses at the 500 had grown painfully long. He was leading with three laps to go in 1986 when the fuel tank ran dry. In 1990, he commanded 155 laps but lost a sure win after blowing a tire with half a lap left.

Three years later, he led 107 laps only to be overtaken by Dale Jarrett in the trioval on the final lap. In 1997, while duking it out for second with Jeff Gordon, Earnhardt flipped on the backstretch with 12 laps remaining.

Everything changed in 1998. That February, Dale Sr. seized control of the race’s final chapter, leading 69 of the closing 70 laps and finally putting the Daytona 500 ghost to rest.

And maybe it came as sheer luck that he received in the form of a penny from six-year-old Wessa Miller, a child born with spina bifida, who was brought to the track by the Make-A-Wish Foundation, but his car certainly was another factor that drove him to the front until the end.