If you’ve watched even ten minutes of NASCAR in the last two decades, you know the name Kyle Busch. He is arguably the greatest talent of his generation, a man with over 230 wins across NASCAR’s top three national series. He has two Cup Series championships. He’s won the Brickyard 400. He’s won at every active track on the schedule.
But there is a gaping, jagged hole in his resume. It’s shaped exactly like the Harley J. Earl Trophy.
Kyle Busch Daytona 500 attempts have become a annual tradition of "what could have been." We are talking about 20 starts. Twenty years of showing up in February, often with the fastest car, and leaving with nothing but a wrecked Chevy or Toyota and a very salty post-race interview. Honestly, it’s starting to feel like a curse. You’d think by sheer accident he would’ve lucked into one by now, right?
He hasn't.
The 2023 Heartbreak: Leading at Lap 200
The 2023 race was peak Kyle Busch. It was his first "Great American Race" with Richard Childress Racing after that messy divorce from Joe Gibbs Racing. He was driving the No. 8 car—the same number Dale Earnhardt Jr. made famous. The narrative was perfect.
And for 199 laps, it looked like the streak was finally over.
Busch was leading when the white flag should have waved. If this were 1998, he would have been the champion. "I wish it was 1998 rules," he muttered after the race. But it wasn't 1998. It was the era of "overtime," and a late spin by Daniel Suarez forced a green-white-checkered finish.
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On the restart, things went south. Fast. Busch got shuffled, then caught in a massive 13-car pileup. He finished 19th. While Ricky Stenhouse Jr. celebrated in Victory Lane, Busch was left explaining to reporters how he’d led the most important lap of the race and still lost. It was his best chance in years, and it vanished in a cloud of tire smoke and bent sheet metal.
A History of Near-Misses and Dominance
To understand why this is so frustrating for Busch fans, you have to look at the sheer numbers. This isn't a guy who just isn't good at Daytona. He’s actually great at it. He won the summer race there in 2008. He’s won the Clash. He’s won his Duel qualifying races.
He has led 324 laps in the Daytona 500 throughout his career. That is the most of any driver in history who hasn't actually won the race.
The 2008 Statement
His first year with Joe Gibbs Racing was a statement of intent. Busch led 86 laps—the most of anyone that day. He was the dominant force. But in the draft, dominance doesn't mean safety. He got shuffled back late and finished 4th.
The 2019 Runner-Up
Busch finished 2nd to his then-teammate Denny Hamlin in 2019. It was a clean race, mostly. He just didn't have the help behind him to make the winning move on the final lap. It was a professional finish, but for Rowdy, second place is just the first of the losers.
The 2025 Wreck
The most recent attempt in 2025 didn't go any better. On lap 186, while running in the lead pack, he got swept up in a "Big One" triggered by Joey Logano and others. He ended up 34th. Same story, different year.
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Why Can’t He Close the Deal?
It’s tempting to say he’s "unlucky," but in a race like the Daytona 500, luck is a measurable stat. Superspeedway racing is about 30% skill, 30% car prep, and 40% being in the right place when someone else makes a mistake.
Busch is an aggressive driver. He’s "Rowdy." He likes to control the pace. But at Daytona, controlling the pace makes you a target. You’re the one everyone is trying to leapfrog.
There's also the "teammate factor." In 2023, he had Austin Dillon behind him ready to help, but the chaos of the draft broke them apart. In his Gibbs days, he often found himself at odds with Denny Hamlin or Joey Logano (when Logano was there). Without a dedicated "pusher" who is willing to sacrifice their own win to help you, winning the 500 is nearly impossible.
The Earnhardt Parallel
NASCAR fans love a good historical comparison. Dale Earnhardt Sr. famously tried 20 times to win the Daytona 500 before finally doing it in 1998.
Busch has now hit that 20-start mark.
The parallels are eerie. Both were polarizing figures. Both were arguably the most talented drivers of their respective eras. Both won everything else there was to win before finally (hopefully) conquering the 500. If the script holds, Busch is due for his "walk through the pits" moment very soon.
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What Most People Get Wrong About His Strategy
Critics often say Busch is "too aggressive" at Daytona. That’s a bit of a lazy take. If you look at his recent runs, especially since 2022, he’s actually been quite patient. He often hangs out in the back for the first two stages to avoid the mid-race wrecks.
The problem is the "Next Gen" car. These cars are harder to save when they get sideways, and they require much more aggressive pushing to make a pass. Busch has adapted his style to be a "pusher" and a "leader," but he keeps getting caught in "the accordion effect"—where one car taps another, and five cars back, someone hits a wall.
What’s Next for Rowdy?
As we head toward the 2026 season, the pressure on the No. 8 RCR team is immense. Busch is currently on the longest winless streak of his career. Winning the 500 wouldn't just be about the trophy; it would be about proving he’s still the elite "Tier 1" driver everyone knows he is.
Here is what he needs to change to finally get it done:
- Loyalty in the Draft: He needs to find a manufacturer partner (like a fellow Chevy driver) who is willing to stay on his bumper for the final 10 laps, no matter what.
- Overtime Management: He’s lost the lead in overtime multiple times. He needs to figure out how to defend both lanes better when the field is bunched up for a two-lap sprint.
- Avoiding the Duel Damage: In both 2023 and 2024, he wrecked his primary car in the Duel qualifying races. Starting the 500 in a backup car puts you at a disadvantage before the green flag even drops.
Actionable Insights for Fans and Bettors
If you’re looking at the Kyle Busch Daytona 500 odds for next year, keep an eye on his practice speeds and his teammate’s qualifying position. If Austin Dillon or another Chevy driver is starting near him, his chances of staying at the front skyrocket.
Don't bet on him because of "luck." Bet on him because he is the only driver in the field who knows exactly how not to win this race, having tried every way possible. Eventually, the only path left is the one that leads to the winner's circle.
He’s already a Hall of Famer. But until he gets that Daytona 500 win, there will always be a "but" at the end of his career summary. And for a guy as competitive as Kyle Busch, that "but" is probably the only thing that keeps him up at night.