48.932 seconds! That’s all it took for Kyle Busch to flip the script on nearly two decades of Daytona heartbreak. Under the bright Wednesday night lights at Daytona International Speedway, Busch stunned the field with a blistering pole-winning lap, making it his first-ever for the Great American Race. And suddenly, the narrative shifted. After 20 winless Daytona 500 attempts, the two-time Cup champion isn’t just fast… he’s chasing history. Busch now enters 2026 with a rare chance to accomplish what no driver has ever done: earn his first Daytona 500 victory after start No. 20.

Kyle Busch eyes the one trophy that’s always escaped him

For Kyle Busch, the mission is simple. Even if history suggests otherwise.

“It’s a box we got to check. So here we are. This is the opportunity to be able to do that. I’ve come down here a lot of years and I think I finished in about every position possible. So, it’d be nice to close out 2026 with a victory here in the Daytona 500.” Those words aren’t just optimism from ‘The Rowdy.’ They’re the words of a driver reckoning with a two-decade-long curse at NASCAR’s biggest race.

Busch has won everywhere, in everything, and in nearly every way imaginable. Yet the Daytona 500, the crown jewel of stock car racing, remains the one achievement he’s never been able to conquer. The 2026 running will mark his 21st attempt, and while sitting on the pole gives him momentum, the statistics paint a difficult picture. No driver has ever earned their first Daytona 500 victory after making more than 20 starts. Not even legends could break that barrier.

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The closest comparison? The great Dale Earnhardt himself. The Intimidator famously needed 20 tries before finally winning his first (and only) Daytona 500 in 1998. Driving the iconic black No. 3, Earnhardt dominated, leading 107 laps en route to ending decades of heartbreak. His emotional victory, however, would stand alone. As you guys know, he tragically passed away three years later in the 2001 Daytona 500.

For Busch, the ghosts of Daytona past linger. His last Cup win came in 2023, and since then, a 92-race winless streak has shadowed his career transition with Richard Childress Racing. But landing the 2026 Daytona 500 pole? That’s the glimmer of hope he (and RCR) desperately needed.

Now, with history staring him down, Busch isn’t just chasing a victory. He’s chasing validation, redemption, and one last missing piece to a Hall of Fame résumé.

The parallels between two RCR legends

Every Daytona 500 storyline eventually circles back to one man and one man only – Dale Earnhardt. And as Kyle Busch enters his 21st attempt winless, the similarities between the two RCR icons have become impossible to ignore.

Earnhardt’s legendary breakthrough in 1998 wasn’t just a victory; it was a culmination of heartbreak, superstition, grit, and fate. He qualified fourth and went on to win his Twin 125, but the moment everyone remembers happened before he even strapped into the car. A 6-year-old fan named Wessa Miller handed him a lucky penny.

Earnhardt glued it to his dashboard, and that penny rode with him for all 200 laps as the Intimidator finally conquered the one race that had tormented him for 20 years. The final laps were a perfect blend of chaos and destiny. Earnhardt led Bobby Labonte and Jeremy Mayfield when Lake Speed and John Andretti made contact and spun, triggering the caution that would decide everything.

Racing back to the yellow flag, the trio closed in on Rick Mast’s lapped car. Earnhardt sliced past Mast on the outside with veteran precision. Labonte lost his draft while Mayfield charged low, trapped behind Mast. Side-by-side behind him, the two challengers could only watch as Earnhardt captured both the white and yellow flags, and finally, mercifully, the checkered. It ended a 59-race winless streak stretching back to 1996.

Fast-forward to 2026, and Kyle Busch finds himself in a surprisingly similar position.

Like Earnhardt, Busch is an RCR driver.

Like Earnhardt, he is winless at the Daytona 500.

And like Earnhardt, he enters the race carrying the weight of a long drought (his last Cup win coming in 2023).

Both men arrived at Daytona with something to prove. Only one ever broke the curse. Now it’s Kyle Busch’s turn to try.