"20 years of trying, 20 years of frustration…"
Every NASCAR fan immediately recognizes those words, spoken in the final moments of the 1998 Daytona 500. Dale Earnhardt had won everything there is to win at Daytona – and to this day, no driver has more victories than him at the Florida superspeedway. However, it took him two full decades to claim the biggest prize of them all. In an unprecedented show of respect, every member of every crew then lined up on pit road to congratulate ‘The Intimidator’ after the checkered flag.
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Buddy Baker was the closest to matching Earnhardt, driving the 'Gray Ghost' to victory in his 18th attempt. For Darrell Waltrip, the No. 17 won in its 17th attempt where he did his own version of the ‘Ickey Shuffle’ in Victory Lane. David Pearson is the second-winningest driver in the history of the Cup Series, but his only 500 win came in his 16th start. Looking lower on the list, Bobby Allison and Michael Waltrip won in their 15th start. But only Dale went 0-19 before finally winning NASCAR's crown jewel event.
For some drivers, a victory in the 500 seemed like a certainty and yet, it never came to fruition. Tony Stewart has more wins at Daytona than any driver not named Earnhardt and was a consistent force to be reckoned with on plate tracks, but the 500 still eluded him. Mark Martin nearly toppled Earnhardt’s record in 2007, but lost in a cinematic photo finish in his 23rd attempt. Despite four runner-up finishes between them, both of the Labonte brothers – who each managed to make themselves Cup Series champions – never were able to add the 500 to their Hall of Fame resumes.
And that brings us to the present day. As already stated, no one beyond Earnhardt has made 20+ starts in ‘The Great American Race’ before finally winning it ... but that’s exactly what Kyle Busch is trying to do this year. Busch’s older brother, Kurt, had to wait until his 17th Daytona 500 to win in 2017, but the younger Busch brother is now approaching his 20th attempt – the same as Earnhardt when he won.
Naturally, comparisons are being made as Busch stares down ‘20’ starts in the 500. There’s also the fact that he’s driving for the same team as Earnhardt – Richard Childress Racing, which since that iconic day in 1998 has won the Daytona 500 two more times with Kevin Harvick in 2007 and Austin Dillon in 2018.
Busch has enjoyed an incredible career with two Cup titles and more wins across all three national divisions than any driver in history. He's captured every crown jewel on the schedule, excluding this one. But unlike Earnhardt, Busch hasn’t won nearly as many races at Daytona… .
The driver of the black No. 3 was always a threat at Daytona, making his 20-year wait even more surprising. He won a whopping 34 races at the speedway — a record that is likely never to be broken. Busch has eight wins total at the speedway, and his most recent win on the oval came in one of the Duel qualifying races, nine years ago. But it’s not like Busch has been persona non grata at the 500 either. If fate had been kinder, he could have raised the Harley J. Earl trophy on more than one occasion by now. Here’s just some of the highlights:
The 'almost' Daytona 500 champ
2007: Busch makes the winning move a moment too late and is boxed into the bottom. Exiting the final corner, he loses control from third and ignites a massive pileup behind the race leaders.
2008: In a Penske vs. JGR for the win, Busch pushes his new teammate Tony Stewart while his older brother Kurt pushes Ryan Newman. Ky. Busch loses contact with Stewart on the final lap, allowing the Penske duo to prevail.
2009: Busch leads nearly half the race in a dominant showing before getting taken out in a bizarre wreck as the lapped cars of Dale Jr. and Brian Vickers tangled.
2016: Much like 2007, Busch runs on the bottom while the outside line surges. He doesn't try to take the run, but his teammate directly behind him [Hamlin] does. Busch crosses the line third while Hamlin goes on to win the race.
2019: Busch earns a career-best finish of second in the 500, losing any potential chance at making a run at the win after fighting Logano for the runner-up position.
2023: In his first 500 with RCR, Busch is controlling the race with teammate Austin Dillon right behind him. Their attempts to orchestrate a late-race restart goes awry and Dillon wrecks. Busch is still in contention, but gets wrecked himself on the final lap.
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That 2023 race is especially painful for KB. When a late-race caution for a lone spinner forced the race into overtime, Busch radioed the following words from the lead as the event crossed its scheduled distance: “Back in 1998 that would be the win, boys!” he said, referencing Earnhardt’s 500 triumph. Unlike the Indy 500, NASCAR’s crown jewel event is not guaranteed to end at Lap 200 and Mile 500 in the modern age. In fact, that race ended up being 530 miles – 12 laps further than expected. Between Lap 200 and 212, both RCR drivers were wrecked and a despondent Busch was scored 19th in the final running order.
Earnhardt was on Busch’s mind late in that 2023 race and there’s no doubt the ‘Man in Black’ will be at the forefront of Busch’s mind again, should he be in that same position again this week. Some might be tempted to say that the stars are aligning and that this has to be Busch’s year, but Daytona has proven time and time again that it cares not for what ‘should’ happen. A three-time series champion like Stewart never did win the 500 while a driver like Trevor Bayne managed to win in his very first attempt.
Not the only losing streak to watch
Surprisingly, Busch making his 20th start isn’t actually the longest losing streak in this race. Martin Truex Jr. will be running his 21st Daytona 500. While MTJ has a rough record at superspeedways, he was on the losing side of what turned out to be the closest Daytona 500 finish in history. In 2016, Hamlin beat him to the line by just 0.010s.
Brad Keselowksi will be another driver to watch closely. Making his 16th start in the 500, he’s always a threat at both Daytona and its sister track, Talladega. In 2021, he dramatically crashed while trying to make a last-lap pass for the win on his then-teammate Joey Logano. Neither made it to the finish line.
If Busch pulls it off, the comparisons to Earnhardt will be immediate, and it's not just the media making that connection. “You’d certainly like to hope so," said Busch on Media Day, who has led 342 laps in his Daytona 500 (more than any other driver without a win).
"Twenty years of trying. There was another storied racer of the past that won on his 20th try and that was a pretty big deal. He was a former RCR driver as well so it’d certainly be nice to win that race and do it with RCR in the No. 8 Chevrolet. That would be pretty cool.”