Dale Earnhardt Jr. recently shared his take on Wood Brothers Racing driver Josh Berry’s struggles this year, stating that Berry’s disappointing 2026 NASCAR Cup Series season is difficult for him to watch, especially given the long personal history the two share.
On the latest episode of Dale Jr. Download, Dale Earnhardt Jr. spoke openly about former JR Motorsports star Josh Berry’s struggles with the Wood Brothers, questioning what has gone wrong for a driver he still believes has the talent to succeed at NASCAR’s highest level.
Berry currently sits 33rd in the 2026 Cup Series’ points with 233 points after 20 races. The Tennessee native has no wins, no top-five finishes, and only two top-ten results. Adding to these counting stats, the No. 21 team has an average starting position of 24.9, an average finish of 27.4, and has led only 16 laps all season.
The most recent stretch has been especially frustrating. Berry finished 29th at Charlotte Motor Speedway, 15th at Michigan, 33rd at Pocono, 29th at Naval Base Coronado, 28th at Sonoma, and 33rd at Chicagoland.
In response to this start to the season, and continued struggles this past weekend, Earnhardt said, “It’s heartbreaking for me because I think of Josh as a family member. Josh Berry moved here from Nashville, moved in with my mom and Willie, ate their dinners, worked at the shop. He raced with us for 10 years.”
When Berry raced for JR Motorsports, he established himself as a highly successful Late Model racer before getting his opportunity in the Xfinity Series and eventually moving into the Cup Series.
Berry’s rise came after years of work, and his path to NASCAR’s top level was hardly the conventional route. For Junior, seeing that journey reach the Cup Series has seemingly made Berry’s current struggles particularly painful.
Berry joined Stewart-Haas Racing’s No. 4 Ford following Kevin Harvick’s retirement and eventually moved to the Wood Brothers, where he scored his first Cup Series win at Las Vegas in 2025.
While talking about the 35-year-old driver, Dale Jr. remembered the excitement surrounding Berry’s arrival and the positive feedback coming from inside Team Penske when he made the move to WBR in 2025.
“We won Xfinity, O’Reilly races. We did everything we could to give him everything we could give him. And he was presented this opportunity to race at Haas following Harvick into the 4 car after Harvick’s retirement. There was this big announcement. I mean, it was emotional. It was cool. And he ends up winning his first race for the Wood Brothers. I’m hearing Penske was very high on Josh.” — Dale Earnhardt Jr.
The 2021 Hall of Famer also pointed to the strong reputation Berry had developed among his fellow drivers. According to him, Ryan Blaney and others within the Penske organization viewed Berry as a valuable teammate and a positive addition to the operation. His early Cup career seemed to suggest that he was on the right trajectory.
However, the problem is that the momentum has not carried into 2026. Berry’s third-place finish at Nashville was proof that the speed has not completely disappeared.
Still, the bigger issue has been consistency. Berry has struggled to put together the kind of season that would strengthen his position in the Cup Series. The veteran driver admitted he does not have an explanation for the sudden downturn.
That’s why, without placing the blame squarely on Berry or the Wood Brothers, Earnhardt Jr. stated that the deal “Looked like it was going to be positive. And I don’t know. I do not know what has happened. I really don’t. I don’t bug Josh too much about it. I think the world of the Wood Brothers, I idolize Leonard and them.”
Earnhardt, having been a part of the sport for nearly three decades now, knows how difficult the current Cup Series landscape can be for drivers who are struggling to produce results, particularly when opportunities at competitive teams are limited.
“I don’t know what has happened. It’s unfortunate because I don’t know where this goes for Josh.”
With the Wood Brothers currently struggling to produce competitive results regularly, Berry has not been able to build the momentum that Earnhardt Jr. believes his talent deserves ahead of another free agency cycle for the veteran driver.
“The landscape right now is crappy for guys like him. I don’t know what opportunities even exist. It’s heartbreaking because, man, he has worked his ass off to get to this point.”
He believes Berry has already demonstrated enough ability to justify remaining at NASCAR’s top level and hopes the second half of the season can provide the results needed to change the conversation around his future.
Meanwhile, for Berry, the remaining six races in the regular season will be extremely important. A few strong finishes could change the perception surrounding his season and give the Wood Brothers team something positive to build on.
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