The NASCAR Cup Series playoffs have already produced some unexpected twists so far, and Josh Berry’s last two races have been a part of it. Driving the iconic No. 21 for Wood Brothers Racing, Berry opened his first playoff run with a devastating 38th-place finish at Darlington after an early crash left him 128 laps down. Gateway was supposed to offer redemption, but instead, his campaign unraveled further, where he finished 36th. With only one race left in the Round of 16, he now sits at the bottom with 45 points below the cut line, on the brink of elimination. That grim position has also brought out an emotional reaction from his longtime mentor, Dale Earnhardt Jr.

Berry’s struggles cut deeper because of his history with Earnhardt Jr. A late bloomer in the sport, Berry spent years working his way up through short-track racing. This was before Earnhardt Jr took a chance on him at JR Motorsports. Together, they built a story of perseverance that culminated in multiple Xfinity Series victories. This eventually opened the door to a full-time Cup ride. Now, in his first postseason at NASCAR’s top level, Berry carries experience. He has the legacy of Wood Brothers Racing and their alliance with Team Penske. Moreover, he has to live up to the faith Dale Jr. placed in him. That clash of promise and results is what led Earnhardt Jr. to speak so bluntly about his driver’s predicament.

Dale Earnhardt Jr. gives his brutal assessment of Berry’s playoff woes

On his Dirty Mo Media podcast, Dale Jr. did not hold back as he reflected on Berry’s back-to-back crashes. “Josh Berry had another… He’s had the two worst weeks you could possibly have. Terrible,” he said, summing up the disastrous start to Berry’s postseason. The comment highlighted not only the disappointment in the results but also the reality that Berry’s margin for error has disappeared entirely. The remark captured just how crushing these weeks have been for a rookie trying to establish himself on NASCAR’s biggest stage.

The frustration extended beyond the finishes themselves. Dale Jr. broke down the Gateway crash in detail. He pointed to Chase Elliott’s move underneath Berry before sliding up into the No. 21 Ford. “I know that Chase dove down into the corner underneath him and got up the track a little bit. Just got into the left rear quarter panel of the 21 car,” he explained. That contact sealed Berry’s day before Stage 1 ended and stripped him of the chance to repair his playoff standing. For a driver needing a turnaround, the blow could not have come at a worse time.

Dale Jr. and his co-host TJ Majors also lamented how Gateway should have played into Berry’s hands. “Being the short tracker I think Josh probably had a good shot of having a good run,” Majors said, with Dale Jr. echoing the sentiment. “I felt like that was if there was a racetrack where you felt more confident to get a good run.” Instead, what was expected to be a confidence boost turned into another wrecked car, leaving Berry in a must-win situation at Bristol.

Looking ahead, Berry’s playoff hopes now rest entirely on the Bristol Night Race, a track where his short-track roots may give him a fighting chance. Analysts have pointed to his tire management skills as a potential edge under NASCAR’s new softer right-side tires. Still, with the stakes at their highest and Dale Jr. himself admitting the past two weeks have been “terrible,” the challenge is monumental.

Josh Berry on his WWT spin-out

Josh Berry’s playoff run went from bad to worse at Worldwide Technology Raceway, as his clash with Chase Elliott left the No. 21 Wood Brothers Racing Ford parked early for the second straight week. Berry, who made the postseason with his Las Vegas triumph, now sits in a deep hole heading to Bristol with elimination looming.

The incident unfolded on Lap 35, when Elliott’s No. 9 Hendrick Motorsports Chevrolet slid into Berry entering Turn 1. Berry’s Ford crunched the outside wall before limping back to the garage with heavy damage, ending his day at the Enjoy Illinois 300. Elliott recovered to finish third, but not before taking time to apologize. “I had no intention of getting into him,” Elliott said, stressing his respect for Berry and the 21 crew.

Berry, who once filled in for Elliott during his 2023 snowboarding injury absence, chose not to assign blame. “It looked like Chase just made a late move and got a little loose… just an unfortunate scenario,” he said. For Berry, the early exit followed a last-place result at Darlington, marking back-to-back playoff disasters in what has quickly become a nightmare start to his Cup postseason career.

With a 45-point deficit below the elimination line, Berry faces a must-perform situation at Bristol Motor Speedway. “We’ve got no choice,” he said, determined to lean on his team’s effort despite the setbacks. The bottom four will be cut after Saturday, leaving Berry’s playoff hopes hanging by the thinnest thread.