Josh Berry knows better than most that getting to the NASCAR Cup Series is only half the battle. Staying there is a different fight. Sixteen years ago, he was working as a bank teller in Hendersonville, Tennessee, squeezing in local Legends races whenever he could afford them. Today, he’s a Cup winner. Yet somehow, his future in the sport remains uncertain, and that’s the reality Dale Earnhardt Jr. opened up about this week. It hit closer to home than most driver stories do.
“It’s heartbreaking for me because I think of Josh as family,” Earnhardt said on The Dale Jr. Download podcast. And for him, that isn’t just a figure of speech.
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Dale Jr. has watched every step of Berry’s journey. Earnhardt explained that Berry’s connection to his family goes back much further than NASCAR fans might realize.
“Josh Berry moved here from Nashville, lived with my mom, ate dinner with my family, worked at the shop, and raced with us for 10 years. We won hundreds of races, track championships, a national championship, Xfinity [now O’Reilly Auto Parts] races, everything we could possibly do to give him every opportunity,” he stated on The Dale Jr. Download podcast.
That started in 2010 after Earnhardt spotted Berry’s talent through iRacing. Berry left his bank job and joined JR Motorsports as a mechanic, sweeping floors, cleaning race cars, and working in the shop by day before racing Late Models at night. With little money, he even lived with Dale Jr.’s mother, Brenda Jackson, until he could get on his feet.
Years of grinding finally paid off. Josh Berry became one of short-track racing’s biggest stars, won the 2020 NASCAR Weekly Series National Championship, got an Xfinity opportunity with Dale Jr.’s team, and eventually reached the Cup Series after impressing as Hendrick Motorsports driver Chase Elliott’s substitute driver in 2023.
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When Stewart-Haas Racing shut down in 2024, Earnhardt was one of Berry’s biggest supporters behind the scenes. He pushed hard for the Wood Brothers Racing seat, believing Berry was ready. That faith looked justified when Berry won his first Cup race at Las Vegas in 2025 and helped deliver the team’s historic 101st victory.
Now, Berry’s future is suddenly uncertain. That’s why Earnhardt admitted he can’t make sense of what’s happened since.
“Then he got the chance to replace Kevin Harvick… Then he wins his first Cup race with the Wood Brothers… They had a really solid first year… It looked like everything was headed in a positive direction. I don’t know what has happened. I really don’t.”
Josh Berry is 33rd in the standings after a season full of crashes, mechanical issues, and missed opportunities. Wood Brothers Racing has already decided not to exercise its option for 2027, with 2025 NOAPS champion Jesse Love expected to take over the No. 21 Ford.
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Earnhardt said he hasn’t pressed Berry for answers because he respects both the driver and the Wood Brothers organization too much.
“It’s unfortunate because I don’t know where this goes for Josh. The landscape right now is tough for drivers like him. I don’t even know what opportunities are out there.”
That uncertainty is made worse by today’s Cup market. Most seats are already locked down, and Josh Berry doesn’t have the personal funding many teams now expect. Even though many of his poor results came through bad luck rather than a lack of speed, the standings rarely tell that story.
For now, all Josh Berry can do is keep fighting. With races still left this season, every weekend is another chance to remind the garage of his talent and grit, which is what got him here in the first place.
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The post “I Don’t Know Where This Goes”- Dale Jr Breaks Silence On Cup Star’s Career Distress With Heartbreaking Confession appeared first on EssentiallySports. Add EssentiallySports as a Preferred Source by clicking here.
