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This year’s Silly Season got a bombshell announcement this past week as Josh Berry broke the news, later confirmed by the Wood Brothers, that he will not be returning to drive the #21 Ford in 2027.
Maybe I just don’t have the resources that others have (which is probably why two or three hits on each post is considered a bonanza week) but this came out of nowhere for me. It also raised a number of questions. Where will Berry end up? Who gets the famed #21 ride?
And if you think those are the only questions that will need to be answered due to this move, well, there’s a whole lot more where that came from. If Berry was retiring from Cup and heading back to Late Models, the secession plan would be simple, get someone from the O’Reilly Series and put them in the seat and look for a young driver from the regional series to, in turn, replace them in their former O’Reilly Series ride. Where it gets tricky – and rather mind-bending – is the moving pieces in the national series.
Most pundits, official or otherwise, seem to expect that Richard Childress Racing’s Jesse Love will be named to take over for Berry at the Wood Brothers.
In any sport, there are instances where an athlete will find his way to the major leagues blocked by the plans of the team. Example: If a shortstop was coming up through the Baltimore Orioles system in the 1980s and 1990s, they knew their major league options were limited with Cal Ripken, Jr. cemented in that position for literally EVERY game for fourteen straight years.
Austin Hill is currently in the #33 Cup car at RCR and set to be there for the remainder of the 2026 season. There has been a lot of discussion about Noah Gragson leaving Front Row Motorsports and finding his way to that seat in 2027.
However, if the deal with Gragson falls through, one must assume that, of the two RCR drivers in the O’Reilly Auto Parts Series, it would be Hill and not Love who gets tabbed to take over the second Childress Cup car next season. After all, if the plan was to put Love in the #33 next year, one would assume he’d be getting as much experience as possible now.
So, if the online rumours are to be believed, it would certainly appear that Love has two blocks to driving a Cup car for Richard Childress in 2027, an incoming Noah Gragson and teammate Austin Hill already occupying the seat.
Love has two choices. He can either spend another year in the O’Reilly Auto Parts Series or he can look for opportunities elsewhere. With three full years in the O’Reilly series and a championship to boot, Love has all the experience he needs to make the move to Cup. As I stated in a previous article, it’s doubtful that RCR would expand to three cars. Short of Austin Dillon retiring and giving Love the #3 RCR Chevrolet Cup car, a move beyond the organization is the only route he can go.
But, even if Love decides to stick around in the O’Reilly Series, who else could step into the Wood Brothers ride?
- Layne Riggs has been rumoured to be headed to the Cup Series and is already in the Ford pipeline, having driven for Front Row Motorsports in the Truck Series. If it were me, I’d have Riggs drive at least a season or two in the O’Reilly Auto Parts Series. He’s having a lot of success in the Trucks but I still think a jump to Cup would be too big a jump and too soon for Riggs.
- Does Noah Gragson leave Front Row but stay in the Ford camp and end up with the Wood Brothers? In which case, Riggs still comes up to Cup but in the ride that Gragson departed at Front Row.
- What about Austin Cindric, currently without a contract for next season? His father, Tim, is back with Team Penske so Austin’s position isn’t as precarious as it once was. Still, that doesn’t mean that Austin, should he fail to make the Chase, might be out at the main Penske camp. Having said that, he could remain on the periphery with the #21 ride with the Wood Brothers. As far-fetched as that might be, it would raise the question of who replaces him in the #2 Ford? Could Penske see Jesse Love as having a better future return on investment than Cindric? Could Penske placate Tim by retaining Austin but still get Jesse Love for his Cup team?
But no matter who drives for the Wood Brothers next year, another question is about the future of Josh Berry. Does he remain in NASCAR at the Cup Series level? This weekend at Pocono will mark his 100th Cup start and while that is a substantial number, it also feels like Berry just got here. He’d had success in the O’Reilly Auto Parts Series, driving for JR Motorsports, before coming up to Cup in the #4 Ford for Stewart-Haas Racing. He nabbed a win for the Wood Brothers last season so while a return to the O’Reilly Series isn’t completely out of the question, I’m thinking he either looks for another Cup ride or leaves the sport entirely. Does Berry head to Front Row if Gragson leaves for RCR (or the Wood Brothers)?
If Love leaves for the Wood Brothers and Hill remains in Cup as the driver of the #33 car, the next question is: what becomes of the RCR O’Reilly Auto Parts Series program? While a team like Penske has shut down their once-formidable O’Reilly Auto Parts Series program (although it was largely a seat for drivers like Brad Keselowski and Joey Logano to get more practice at the expense of the series regulars), Hendrick Motorsports has expanded beyond their satellite JR Motorsports team to have a regular presence in the series. Richard Childress is smart enough to know how important the O’Reilly Auto Parts Series has been to developing young drivers. Having had a presence in the series since 1995, it’s doubtful that RCR would close up their O’Reilly shop completely.
Back in the day, RCR also had a truck series that they could elevate drivers from. As it stands now, they’d have to see what other O’Reilly Series, Truck Series and even ARCA series teams have to offer.
Throughout the season, even before his bout with vertigo, Alex Bowman’s future in the #48 was unclear. I’ve seen a couple of hints and rumours that Bowman may leave Hendrick Motorsports not due to any move to oust the driver due to his on-track performance but to focus on his own physical well-being. It’d be a tough move for Bowman and most likely not one that is going to come immediately. He’ll probably try to tough it out as long as he can.
I’m not suggesting that Berry or Riley Herbst, the other driver currently looking for a ride for 2027, would replace Bowman at Hendrick. Neither seem like the right fit for the #48 although of the two Berry might have the inside track due to his history with JR Motorsports. Still, if I was putting money on it, I’d actually pick Rajah Caruth, who has ties with Hendrick through sponsorship and his O’Reilly Series ride with JR Motorsports. (I know the more popular pick might be Corey Day but I think he needs more experience.)
My predictions for the 2027 rides in question (as of June 11, 2026)
- #21 Wood Brothers Ford: Jesse Love
- #33 Richard Childress Racing Chevrolet: Noah Gragson
- RCR O’Reilly Auto Parts Series rides: Austin Hill and Christian Eckes
- #48 Hendrick Motorsports Chevy: Rajah Caruth
- #4 Front Row Motorsports Ford: Layne Riggs
- Josh Berry: returns to JR Motorsports
- Riley Herbst: Goes to Legacy Motor Club’s third charter
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