For two decades, Denny Hamlin has lived with the cruelest label in NASCAR: the best driver to never win a championship. Sixty career wins, three Daytona 500s, and a Hall of Fame résumé say one thing, but that empty championship column says another.

Now, at 44, Hamlin is back in the Championship 4, trying once again to finish the story that has haunted him for 20 years.

Denny Hamlin’s endless chase

There’s a moment in one of Denny Hamlin’s The Athletic interviews that feels like it sums up two decades of chasing the one thing he’s never held. Sitting back, half-grinning, he said, “I’m not going to kid myself or downplay that this is a great opportunity. But have I mentioned this is one race?” It’s the kind of line that sounds confident, but if you listen closely, it carries a lifetime of near-misses, heartbreaks, and hard lessons learned in the cruelest playoff format in motorsports.

Hamlin’s résumé is the definition of greatness: 60 wins, three Daytona 500s, and a guaranteed spot in the Hall of Fame. Yet, year after year, one empty box shadows all of it, a Cup Series championship.

For twenty seasons, he’s been close enough to touch it, five times in the Championship 4, four others eliminated by bad luck or heartbreak, and every time, the trophy’s slipped away. He’s 44 now, the oldest full-time driver in the field, and this Phoenix finale might be his last, best shot to silence the one knock that’s followed him his entire career.

The irony is, this might be his most unlikely run yet. When the 2025 season began, Hamlin’s No. 11 team looked more uncertain than it had in a decade. FedEx, his career-long sponsor, was gone. Joe Gibbs Racing shuffled crew chiefs, replacing Chris Gabehart with Chris Gayle.

And off the track, Hamlin found himself juggling a federal court case as 23XI Racing co-owner in an antitrust battle against NASCAR. “We rolled in with no sponsors, a new crew chief, all that. I was looking for any glimmer of hope,” he said.

That hope came quicker than expected. Gayle, a quiet but sharp-minded engineer who once led Erik Jones’ Cup effort, found instant chemistry with Hamlin. The two started fine-tuning setups that fit Hamlin’s ultra-detailed style, leading to six wins, more than any other driver this season.

“I was probably more pessimistic at first,” Hamlin admitted. “But I realized [Gayle] could give me what I need to win. With the right people around him, and when he gets the information he’s seeking, he can do great things with a car.” For a driver who’s seen eras, teams, and technology shift beneath him, Hamlin’s adaptability remains his edge.

“I always want change,” he said. “Do not let it sit and get too stagnant, because everyone is going to catch up eventually to whatever I feel like my edge is. I absolutely love change.” That attitude has defined him across four generations of Cup cars, from the high-downforce Gen-6s to today’s unpredictable Next Gen machines.

“I just do my best to figure out how to make speed out of whatever the change is,” he said. That relentless curiosity, not just talent, has kept him relevant long after most drivers his age have stepped away.

Still, no amount of preparation guarantees good fortune. From the blown tire that cost him a title shot in 2010 to pit road mistakes in 2019 and mechanical failures in 2021, Hamlin’s playoff heartbreaks are NASCAR folklore by now. “Truthfully, in the bucket of luck, my career luck in the playoffs has been freaking horrible,” he said on his podcast. “I only need it to be good for one more week. That’s it. Just hang on for one more week.”

And that’s where the story comes full circle. The driver who’s done everything, built his own race team, survived sponsor exits, evolved through eras, and outlasted most of his peers, is once again one race away from rewriting his legacy.

Whether he finally lifts the Cup or not, Hamlin’s place in NASCAR history is secure. But for a man who’s spent 20 years watching the ultimate prize slip through his fingers, this Sunday at Phoenix isn’t just another chance. It’s a test of everything he’s ever been: resilient, relentless, and still chasing the one thing that’s always been just out of reach.

Kenny Wallace bets on Hamlin

Kenny Wallace threw his hat in for Denny Hamlin as the Phoenix champ, edging out William Byron, Kyle Larson, and Chase Briscoe. After Martinsville locked the final spots, Byron and Larson joined Hamlin and Briscoe, and Wallace made his call on X.

He said, “I say, my choice is gonna be Denny Hamlin. To win it out with William Byron, those two are gonna go at it. But I think is gonna win it all. I want him to win it all. This is because of my feeling that Denny’s gonna run a couple more years, his clock is ticking, and I think it’d be a great win.”

Wallace sees the urgency. Hamlin’s first Championship 4 since 2021 feels like now or never. A win ends two decades of close calls for the No. 11. Byron, last year’s third, pushes hard with Larson and Briscoe in the mix. But Wallace roots for the vet to grab it while time allows.

Hamlin’s journey ties the picks together. Twenty years of grit meet one race. Wallace’s nod echoes the hope, the clock ticks, but the chase burns on.