NASCAR

3 NASCAR Cup Series Drivers Rapidly Running Out of Chances To Win the Daytona 500

Disclosure
We publish independently audited content meeting strict editorial standards. Ads on our site are served by Google AdSense and are not controlled or influenced by our editorial team.
Kyle Busch looks on during qualifying at Daytona International Speedway on Feb. 15, 2023.

The Daytona 500 is an extremely difficult race to win. Not that anyone ever doubted it, of course.

Need some quick proof, though?

It took the late, great Dale Earnhardt 20 tries to get it done.

Darrell Waltrip needed 17. Kurt Busch required 16.

Many retired NASCAR Cup Series legends — Mark Martin, Rusty Wallace and Tony Stewart, among them — went 0-for-their-careers in The Great American Race.

Given this, it’s no surprise that several of the Cup Series’ most accomplished active drivers don’t possess a Harley J. Earl Trophy.

Of those drivers, three stand out above the rest as rapidly running out of opportunities.

Here’s a breakdown of the big trio and their chances of finally carving out a piece of Daytona glory.

Kyle Busch, age 39

Good luck finding anyone who’s faced more Daytona 500 heartache than the younger Busch sibling, who is the all-time wins leader across NASCAR’s three major stock car series.

He’s finished second (2019), third (2016) and fourth (2008). In the 2009 Daytona 500, he led over half the race before wrecking out.

Busch owns one points-paying Cup Series victory at The World Center of Racing, where he prevailed with Joe Gibbs Racing in July 2008. In last August’s Daytona event, the two-time NASCAR Cup Series champ led coming to the white flag before getting the short end of a last-lap battle with unheralded Harrison Burton. He finished second, a car length behind.

Busch, who turns 40 in May, has undoubtedly entered the twilight of his Hall of Fame career, which has produced not only two Cup Series championships but 63 premier series triumphs among other highlights.

2024 was Busch’s first season since the joining the Cup Series full time in 2005 that he didn’t go to Victory Lane. So, to end his highly publicized drought by finally exorcising his Daytona 500 demons would be quite the redemption story.

For what it’s worth, this will be Busch’s 20th attempt to win the 500 — the same of number of tries it took Earnhardt. And Busch is entering his third season with Richard Childress Racing — the organization Earnhardt captured his lone 500 victory with in 1998.

Coincidentally, Earnhardt’s Daytona 500 breakthrough came on the heels of a rare winless season. So, maybe, just maybe, all the stars are aligning for Busch in 2025.

Or maybe this be the latest chapter in his proverbial book of Daytona disappointments.

Brad Keselowski, age 40

No one drives more hammer down at Daytona International Speedway than Keselowski. The 2012 Cup Series champ and RFK Racing driver/co-owner’s aggression has triggered several chain-reaction multicar wrecks at the 2.5-mile superspeedway in recent years.

Perhaps the 40-year-old’s no-holds-barred approach to Daytona is a by-product of knowing time is running out for him to finally snare the Daytona 500 win that’s repeatedly escaped him.

How close has Keselowski come to leaving Central Florida in February with a big check and trophy? Arguably not as close as Busch. But he’s been close, nonetheless. He finished a Daytona 500 career-best third in 2014, after coming home fourth one year earlier.

Hands-down Keselowski’s most gut-wrenching Daytona 500 defeat came in 2021 when he and then-Team Penske teammate Joey Logano crashed together while battling for the lead with less than half a lap to go. The accident allowed Michael McDowell, who was running just behind in third, to grab the lead and score an unlikely win.

Keselowski does own a points-paying triumph at Daytona, which he scored in the summer of 2016 while driving for Team Penske.

The biggest barrier between Keselowski and a Daytona 500 breakthrough has been being around at the finish. Keselowski has recorded a DNF in four of his last five starts in The Great American Race. That’s no surprise, however, given his proclivity to set melees in motion on the sport’s biggest stage.

Martin Truex Jr., age 44

Time and opportunities are not on Truex’s side in the Daytona 500. His full-time driving days having ended with the end of the 2024 NASCAR Cup Series season, Truex is on the precipice of what will almost certainly be his final start in the 500.

So, it’s likely quite literally now or never for Truex, whose Daytona 500 shortcomings are best encapsulated in the finish of the 2016 season opener. In that race, Truex fell exactly one-hundredth of a second short of victory. The winner, Denny Hamlin, beat him by a nose.

Truex hasn’t finished that well in the 500 before or since. He’s actually an ugly 0-for-39 in Cup Series points races at the high-banked Daytona Beach track. While Truex won’t be running this Daytona 500 with his former team at Joe Gibbs Racing, he will have technical support from JGR in a car fielded by TRICON Garage — a NASCAR Craftsman Truck Series team owned by former Cup Series driver David Gilliland.

He will also be paired with a familiar face in his former crew chief, Cole Pearn, who’s making a cameo return to the sport just for the occasion. Truex and Pearn claimed the 2017 Cup Series championship together during their days for since-disbanded Furniture Row Racing.

If Truex can somehow find the Daytona 500 magic he’s been missing in 20 previous tries, it’ll be while racing with a heavy heart. The family patriarch, Martin Truex Sr., passed away earlier this month. He was only 66.

“We are devastated by the loss of our father,” Martin Truex Jr. and younger brother Ryan Truex said in a joint statement. “Simply put: He was our hero and a great man. We appreciate everyone’s thoughts and prayers.”