“People get enamored with my story — that I short-track raced for so long and finally got an opportunity — and they’re like… But I don’t view it as ‘I’m just happy to be here.’ I want to be up front. I want to be competitive.” That is what Josh Berry had to say about his image of the underdog. But that doesn’t mean that it has defined Josh Berry’s rookie Cup Series campaign. While many still see him as the grassroots racer who finally broke through, Josh Berry is focused on proving he belongs at the sharp end of the field.

Currently, Josh Berry is under the cut line, the No. 13 seed in the playoffs, and is approaching it with ease. With the playoffs now in motion, he’s not just chasing good finishes; he is chasing moments that can shake up the standings and rewrite his own narrative in the sport.

Josh Berry believes the pressure is on those who are playoff favorites and not the underdogs

Josh Berry may be making his NASCAR Cup Series playoff debut just one point below the elimination cut line, but make no mistake, the real pressure belongs to everyone else. The rookie sensation already pulled off one of the season’s most inspiring upsets, driving the iconic Wood Brothers Racing No. 21 to victory lane in March at Las Vegas Motor Speedway. That win wasn’t just his first at NASCAR’s highest level; it was a career-defining breakthrough for a driver who had spent the past decade grinding it out in Late Model Stock cars. It was the kind of story that made the garage smile: a small-town short tracker is joining forces with the Cup Series’ oldest continually operating team and proving they could take on the giants. And now with the playoffs underway, Berry’s playing with house money.

Fully embracing his underdog role, Berry said, “I mean, the pressure is on the guys that everybody has been calling the favorites … and the pressure is on them to deliver, not us. That doesn’t bother me. I feel like these tracks line up really well for us. I feel like if we can execute a little better and finish where we should, then we are going to keep ourselves in contention.”

Josh Berry’s victory came just five races into the season, the 53rd start of his Cup career, and kept him inside the top 20 points for much of the year. Sure, there have been setbacks; a few costly crashes and road course struggles, by his own admission, have slowed momentum. But with Round 1 featuring Darlington, Gateway, and Bristol, Josh Berry sees a golden opportunity to strike early and set the tone. He explained, “I feel good about a lot of the short tracks and intermediates that we’re going to. You know, nearly each one of those that we went to in the first half, we showed potential, won Vegas, and had some issues with execution here or there, like Phoenix.”

The Roval, he admits, remains his biggest question mark. Road racing has never been his specialty, though he notes it has actually been his best road course to date. The Wood Brothers Racing driver said, “So I feel like we are going to some tracks where we can go run well and score stage points and run inside the top-5 and top-10, and contend. The Roval has to be considered a weakness because road racing has been a challenge, but I also feel like that has been my best road course. If we make it that far, and we’ve made improvements on our program, we might be in trouble if we need to win our way in, but we can still go there and have a solid day, get some stage points, and maybe make it through.”

Over 26 races, he has posted one win, two top-five finishes, and an average finish of 20.8. Closing out the regular season with consecutive top 10 results at Richmond and Daytona, he has shown signs of momentum, but maintaining consistency will be key to advancing deeper into the postseason. And now, as Berry raised his biggest playoff concern: if the 34-year-old can navigate the first round like he did in Las Vegas in March—with patience, precision, and a little shock value—then the rookie could turn his playoff run into something far more than just a feel-good story.

Josh Berry points out the biggest difference between the Cup Series and Late Model Racing

Josh Berry’s climb to the NASCAR Cup Series wasn’t just a career milestone; it was the culmination of a decade-long Late Model dynasty. Growing up in Tennessee, Berry kicked off on karts before dominating Legend cars at the Nashville fairgrounds. His big break came after impressing Dale Jr. via online SIM racing in 2010, which led to his signing with JR Motorsports. From there, Berry built an absolute empire in Late Model Stock Racing, earning the 2017 CARS Tour Championship, winning the 2019 ValleyStar Credit Unit 300 at Martinsville, and capturing the 2020 NASCAR Advance Auto Parts Weekly Series national title.

With 95-late model wins and Xfinity success to his credit, he became impossible to overlook. When asked how living the Cup Series compared to the dream, Berry didn’t mince words. Speaking to Jeff Gluck from The Athletic, he said, “To be honest, it’s way harder than people realize. When I was racing Late Models and winning all kinds of races, you’d see guys come through the ranks — maybe they didn’t even have that much success, but they had funding and opportunities. But living it, you realize just how good everyone is in the Cup Series and how hard it is to be competitive — and how much is outside of your control.”

Those words carry weight. While he once fine-tuned his Late Model on weekends with a tight-knit crew, Cup life is a high-stakes symphony of strategy, pit stops, and restarts, all while racing against elite talent and hyper-engineered machines. And now, as the Cup Series heads to Darlington next, eyes will be on Josh Berry to break his underdog narrative and prove his mettle.