With Josh Berry’s recent announcement that he will not return to Wood Brothers Racing, NASCAR fans are asking which driver is the best fit to take over the iconic No. 21 in 2027.
While many drivers have re-signed with their teams for 2027, few have confirmed plans to hit the free-agent market next year.
The first NASCAR 2027 Silly Season domino to fall was Riley Herbst (as far as free agency goes). Herbst is being replaced at 23XI by Corey Heim.
But unlike Herbst, who has a clear landing spot, with many rumors tying him to Legacy Motor Club’s third full-time car, the No. 84, for 2027, newly announced free agent Josh Berry has an uncertain future.
Still, while questions about where Berry could go are on the minds of fans, for the first time in a long time, a seat in the NASCAR Cup Series garage is open, putting Berry’s replacement at the forefront of Silly Season discussions.
Wood Brothers Racing has yet to announce an official replacement for Berry, but there are some strong contenders across the three NASCAR National Series.
Austin Cindric is a major question entering the latter half of the 2026 season. While he performs well, Team Penske is lagging behind the rest of the garage, leaving Cindric, who is on a contract season, as potentially the odd man out if the team wanted to make a change.
Given Penske’s relationship with WBR, if Penske were to make a dramatic change by targeting a top free-agent Cup Series veteran and wanted to keep Cindric in-house, they could move him to the No. 21.
This would serve the team well and give WBR a driver capable of winning. Still, there is no indication of what Cindric’s future holds beyond the 2026 season, and it might be time to put a younger driver on deck to join the Penske brigade in the future.
At the end of the day, fans would mostly note that in the developmental cycle, Penske, who uses WBR’s No. 21 as a developmental car on occasion, should focus on the future.
So, why not go after the best Ford prospect there is in Front Row Motorsports’ Layne Riggs? Riggs is in his third full-time Truck Series season and looks like he’s ready for the next level. Of course, with no NASCAR O’Reilly Auto Parts Series teams, Penske would need to find a stopgap for the rookie to adjust, something the No. 21 could provide.
Nonetheless, while Riggs’ name is often thrown around in Silly Season discussions, it is mostly in regard to Front Row, given their status as a Tier One Ford team and the investment they have already made in the second-generation driver.
To keep it in the Ford family, why not knock on the door of Riggs’ NASCAR Craftsman Truck Series teammate Chandler Smith? Smith is in his second season in the Truck Series with FRM after taking a step down after getting ever so close to a Cup Series ride.
While Smith has seemingly had his ups and downs, the stability of sponsors like Motocraft and DEX could give him a leg to stand on in the Cup Series.
Much like Riggs, however, while Smith’s name has come up in the Silly Season speculation, most have tied it to FRM.
Sticking with the idea of developing for the future, one of the biggest rumors of the 2025 season was that JR Motorsports’ NASCAR OAP Series driver Carson Kvapil had signed as a developmental driver for Team Penske.
While this has yet to be confirmed, Kvapil has carried sponsorship from Clarience Technologies, a sponsor of Team Penske in the NTT IndyCar Series.
Nonetheless, while Kvapil as a candidate for the No. 21 should be on the minds of fans given last year’s rumors, these are, after all, just rumors. Even then, he is still likely not the best possible option in NASCAR’s secondary series.
When fans talk driver promotions for 2027, Jesse Love continues to be part of those conversations. Love is the reigning NASCAR O’Reilly Auto Parts Series Champion, doing so with Richard Childress Racing, but has met dead ends in his pursuit of a Cup Series ride.
Following the passing of Kyle Busch, RCR has opted to use his teammate, Austin Hill, as Busch’s full-time Cup Series replacement for 2026, and, this past weekend at Michigan International Speedway, Richard Childress confirmed that Busch had signed a contract to return to the team in 2027 prior to his passing, suggesting Love was always a long shot for the No. 8/No. 33.
If Love is on the move from RCR, and if Legacy Motor Club (a long-rumored landing spot for Love) opts to go with its 2026 lineup plus Riley Herbst, it would be a no-brainer for Ford and Penske to pursue Love, placing him in the No. 21 for a 2027 rookie campaign.
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