Josh Berry has already clawed his way from short tracks to the NASCAR Cup Series, won at Las Vegas with Wood Brothers Racing, and even made the playoffs in his first full season with the team. But he finds himself without a ride for the 2027 season. With his No. 21 seat gone to Jesse Love, Josh Berry has been making calls, taking meetings, and trying to find a way to stay in Cup. So far, nothing has moved the needle.

“I don’t feel any closer now than I did two months ago. I mean, it’s been a little busier,” Berry said in a post shared on X by Joseph Srigley.

“I mean, we’ve had conversations. I don’t feel any closer now than I did two months ago, if I’m being honest.”

That was the clearest sign yet of how difficult his free agency has become. Josh Berry said some meetings looked promising. Others went nowhere. Then came one particularly difficult request.

“We’ve had, you know, ones that I thought had actual… and ones that we sat down and they asked for $3 million,” he added. “So, it’s been a little bit of a challenge working through all that.”

Berry did not name the team. That leaves the specific identity of the organization open to speculation. Still, the number gives a glimpse into what some Cup teams now expect from drivers trying to secure an open seat.

Josh Berry is not coming from a family fortune or a ready-made sponsor package. He got his career the long way, from working at JR Motorsports to winning Late Model races and eventually breaking into O’Reilly Series. He found his big break at Stewart Haas Racing, but they shut down in 2024, that eventually saw him move to WBR.

Berry’s 2026 season has not helped his case. He has five DNFs in his first 21 starts and sits 33rd in the standings with a career-low 25.5 average finish. Wood Brothers Racing ultimately declined his 2027 option and chose Jesse Love for the No. 21 Ford. And on paper this move makes sense as Love is up and coming talent in NASCAR.

Yet the results do not tell the whole story. Berry has also dealt with crashes and problems outside his control, while Ford teams have struggled for pace across the season. He recently showed what he can still do with a fourth-place finish at Iowa. That is why Berry has now shifted his focus away from the negotiations.

“I kind of feel… I mean, it just shows more about the system than it does about me,” he said, if strong results come and nothing still materializes.

So where could Josh Berry actually land? Kaulig Racing, Front Row Motorsports, and Legacy Motor Club could the teams he’s talking to. If Berry and his management team sat down with an organization like that, a funding request would not be surprising. These are not manufacturer backed tier-1 organizations.

Top teams such as Hendrick Motorsports, Joe Gibbs Racing, or Trackhouse are far less likely suspects. Those already have major sponsorship structures in place and generally recruit drivers for performance, not for a personal check. Berry’s immediate solution is much simpler.

“I can’t do much else other than just try to focus on Sundays,” he said.

That may be his strongest argument anyway. Josh Berry has three races to build on his recent form and show prospective teams exactly what they would be getting.

For now, the $3 million question remains unanswered. More importantly, so does Berry’s 2027 destination.