Denny Hamlin and his retirement plans have been in the air for quite some time now. Even more so after he described his latest contract extension as “most likely” the final one of his NASCAR Cup Series career. But suddenly now his most likely doesn’t seem all that convincing.

This is because Hamlin keeps racing like someone who is nowhere near retirement! And after his latest victory at Pocono, Joe Gibbs Racing co-owner Heather Gibbs might have hinted that a retirement plan reversal might be in the works.

“I think for Denny, he wants to leave on top, right?” Gibbs told FOX following Hamlin’s recent victory at Pocono. “He doesn’t want to leave where it was one year too long. At this rate, what he’s producing out there, it’s not something you would consider. We want the best drivers in our cars. Our teams work to put the best cars on the track.”

Well, that is quite a statement given where Hamlin was just a year ago.

Last season, Hamlin came painstakingly close to winning the first championship of his career before a late-race decision derailed what could have been a perfect afternoon at Phoenix. That loss hurt even more because it came right on the heels of what many thought would be the final contract extension of his career.

Now, at that time, the assumption was that he would race through 2027 and then hand the keys to the next driver. But the timeline feels less certain now, given the things Hamlin has been doing this time.

His victory at Pocono was the first three-race winning streak of his Cup career. He has already collected four wins this season, and has cut into Tyler Reddick’s points lead after what looked like an impossible gap.

Heather Gibbs mentioned that those results have forced the organization to rethink what once felt like set in stone.

“He had records to break,” Heather Gibbs said. “He had something to prove. He’s doing it now. We joked, we were like, ‘You’re a spring chicken, you have so many years left.’ Now we’re trying to think of how we can keep him longer. With Denny, he’s been outstanding.”

The funny thing is, Hamlin is the only person who continues to push back on the idea.

Each time the question of his retirement comes up, his answer has been largely the same. And after his victory at Michigan earlier this season, he went out of his way to explain why.

In short, Hamlin wants to walk away driving like a boss!

“I feel there’s three things that happen,” Hamlin told Dale Earnhardt Jr. “You lose your eyesight. You lose your reaction time. And your body hurts. The body hurts are there. During the week, I’m not recovering as quick. But the other two things, I still feel sharp. So, yeah, I want to go out like this. It’s a fantasy land to do it.” This perspective is also shaped by history.

Hamlin probably has watched plenty of drivers stay far too long in the game. Drivers like Richard Petty, Darrell Waltrip, Terry Labonte, and even Jimmie Johnson all declined late in their careers. Hamlin, for once, knows how quickly things can change once age catches up to you. He is, therefore, all prepped for it.

“If — and that’s a big if — I’m at this point and this fast at this point next year, it would be a tough, tough decision,” Hamlin said. “Because, again, I’m planning for the downfall that I know will come.”

Of course, there are plenty of reasons he could choose to walk away.

The one thing standing between Denny Hamlin and a new JGR deal!

The biggest hurdle being that he co-owns 23XI Racing alongside Michael Jordan. As Gibbs mentions: “He’s got his own team that he kind of wants to run, but it’s hard when we dangle checkered flags in front of them.”

This statement easily symbolizes the biggest conflict of interest in Hamlin’s heart currently. Denny Hamlin is the co-owner of 23XI Racing, and at the same time, he is furiously competing against them for the championship. This makes it difficult for him to pick sides. Whenever he gets behind the wheel, he is expected to show fierce loyalty to JGR.

But as a co-owner, he is also expected to be the mentor to 23XI Racing drivers. Now, Hamlin has been under fire for racing hard against his own team’s drivers multiple times over the years. So it’s no wonder that this situation leads to numerous doubts in Denny Hamlin’s man. He can only juggle two tasks perfectly for so long. At one point, he is bound to lose track of one thing or the other.

That day will be disastrous for all three parties involved. And Heather Gibbs wants to tread this line very carefully when her team tries to approach Hamlin with a contract beyond 2027. For now, Hamlin might insist the plan hasn’t changed. But if he keeps stacking trophies over the next months, then well, Gibbs had said:

“Now we’re trying to think of how we can keep him longer.” And you bet they would give it their all.