Denny Hamlin is one of the very few drivers who check nearly every “all-time great” box. When it comes to longevity, marquee wins, and week-to-week speed, Hamlin delivers, yet the Cup title still dodges him. He’s been in the fight repeatedly and come agonizingly close, but as the years go by, the championship-sized asterisk keeps shadowing an otherwise Hall of Fame resume.

Now, with Denny Hamlin turning 45 this November and signing what he says is most likely his final multi-year deal at Joe Gibbs Racing, running through 2027, the window talk has sharpened. And now, NASCAR insiders have essentially framed this extension as the last big bet on Hamlin’s title push, and it doesn’t sound too positive.

NASCAR Insiders are done waiting, black-flagging Denny Hamlin’s 2025 Championship hopes

Across his near misses, one can trace a clear pattern. He gets to the doorstep and circumstances till the end.

• In 2010, he led the standings into Homestead but lost out to Jimmie Johnson after late setbacks.
• In 2014, he reached the Championship 4 and was outgunned by Kevin Harvick on late tires.
• In 2019, an overaggressive tape call overheated the car and nuked a title shot.
• In 2020, he made the Championship 4 and finished fourth at Phoenix.
• In 2021, reached the Championship 4, finishing third as Kyle Larson’s late pit stop heroics sealed the Crown.

That’s five credible cracks with heartbreak baked in.

But now contract-wise, the latest chapter is official. Last month, JGR announced a multi-year extension that keeps Hamlin in the No. 11 through 2027. He acknowledged that it is most likely his last deal, while noting he’ll keep racing only as long as he is winning at a high level. The announcement also underscored his standing: 58 career wins and the best series win total this season at the time of the signing.

Moreover, reporters have repeatedly characterized the 2025-27 period as the final act, with the retirement possibly very real at the end of the term. Even Hamlin has stopped making further predictions, joking with Jeff Gluck that he’s not good at predicting timelines, another hint that this extension is intended as a sunset run unless the competitive fire and results demand more. But recently, some within the paddock have been more blunt; NASCAR insiders have metaphorically black-flagged Hamlin’s championships.

In a recent interview, when SiriusXM’s Brad Gillie was asked about the possibility of Denny Hamlin being the 2025 NASCAR Cup Series champion, Brad responded immediately. “ Black flag,” he said. “Add ’26,’27,’28 to that as well.” However, Doug Rice chimed in with candid self-awareness.

“I am jumping on the good ship Denny Hamlin; he has dealt with just so much this year. He has crapped in his own mess kit a couple of times, but I think, after all is said and done, maybe this is the year, through all this maelstrom that he’s been through, that he wins the championship.”

On the track in 2025, Hamlin has been in vintage form. With victories at Martinsville, Darlington’s throwback weekend, Michigan via a few economy masterclasses, and the fourth of the season at Dover, even after missing Mexico City for the birth of his son, Hamlin’s 2025 season has been phenomenal. Through it all, he has maintained a leading presence in standings and buzz. However, it is Alexis who pulled the reins on the Joe Gibbs Racing driver in the podcast.

“Black flag. I can’t tell you how many times I’ve said ‘maybe this is the year’ and it wasn’t. So I’m just going to go back and look at what history tells me so until I get proven wrong, which happens quite often, I’m gonna say black flag,” she said.

But as Hamlin is marked as Richmond’s favorite for the weekend, he battles the villain image that he has created among fans. Weighing in on that, Hamlin has made his stance clear.

“I don’t think I’m an a——,” declares Hamlin about his Villain image in NASCAR

Danny Hamlin’s  villain label took on a new twist when Kyle Busch, one of NASCAR’s most notorious drivers, joined him on the Action-Detrimental podcast. In a memorable exchange, Kyle jokingly passed the black hat to Hamlin, symbolically transferring the title of the sport’s most controversial figure. The difference? While Busch has been battling to stay in playoff contention, Hamlin’s momentum hasn’t wavered, sparking frustration and rivalry among competitors like Hendrick Motorsports and their fan base.

However, in a recent candid interview with Jeff Gluck, the Joe Gibbs’ driver addressed the biggest misconceptions about his personality. With his trademark humour, he questioned the notion that he is difficult to like. He said, “I mean, I don’t think I’m an a——. But people don’t think that? Who? Fans from TV interviews? It’s more than likely who have never met me, or saw me walking somewhere, and I didn’t have time to stop. I always try to when I can. Or maybe the trash talking I do on the track makes them think that’s just who I am.”

With critics constantly circling and detractors quick to speak up, a championship win this season could do more than add to his career resume; it might finally change the conversation. Such a victory could shape how fans see him, moving beyond the villain narrative to highlight the complexity of a seasoned driver, a devoted father, and a competitor unwilling to be boxed in by public perception.