Free agency in NASCAR can be a perilous venture, even for an established Cup-level talent like Josh Berry.
Five years ago, Matt DiBenedetto found himself in a strikingly similar position, learning that his days with Wood Brothers Racing were numbered as Harrison Burton prepared to take over the No. 21 for the 2022 season. Now, Berry, in just his second year at the team, is staring down a familiar uncertainty.
For the veteran, however, the hardest part of free agency might not be finding another Cup Series seat. Rather, it appears to be convincing the right people that he deserves one.
Following the Cup Series weekend at Iowa Speedway, one in which Berry cracked the top five for the first time this season, the third-year Cup Series driver offered a remarkably candid look at his situation during Wednesday’s Ford Racing media call.
According to the 35-year-old, the conversations have ranged from genuinely promising to downright frustrating. While some discussions showed promise, others posed a very different kind of hurdle.
“It’s been a little busier,” Berry said. “We’ve had conversations. I don’t feel any closer now than I did two months ago, if I’m being honest.”
Diving into how these discussions have gone, Berry explained, “We’ve had conversations, we’ve had good ones, we’ve had bad ones, we’ve had ones that we thought had potential, we had ones that we sat down and they asked for $3 million dollars.”
That is the hard reality at NASCAR’s elite level. In his case, Berry isn’t exactly approaching free agency with a massive personal fortune, a stellar Cup Series resume, or a ready-made sponsor package that can find him a ride.
In fact, the Tennessee native has already lived the long version of the NASCAR dream, working his way through short tracks, spending time at JR Motorsports, and eventually earning his place in the Cup Series.
On the bright side, that grind got him into the victory lane at Las Vegas with WBR last year, locking himself and the team into the playoffs in his first full season with the organization. Yet now, just as he appeared to have established himself at NASCAR’s top level, Berry is fighting to keep his place.
For 2027, WBR announced they’re moving on, signing Jesse Love to pilot the iconic No. 21 Ford, leaving Berry navigating the free-agent market at a particularly uncomfortable time, and by his own admission, the process has not exactly been encouraging.
Making matters worse is his tumultuous 2026 campaign. Riddled by difficult starts, five disastrous DNFs, and, of course, the Fords struggling to compete against rival OEMs, Berry has fallen down the standings to 30th.
That said, his recent outings are looking considerably more like the driver who earned his Cup opportunity in the first place.
A fourth-place finish last Sunday, after a seventh-place finish at Indianapolis Motor Speedway, has given him consecutive top-ten finishes and a big morale boost for the No. 21. Yet, given the uncertain future that’s in front of him, he is running out of things he can personally do to influence the 2027 Silly Season.
“You know, to be honest, I’m kind of at the point right now where really I can’t do much else other than just try to focus on Sundays and try to have days like we had the last couple of weeks,” Berry said.
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