Five Key 2027 NASCAR Silly Season Questions Still Unanswered

What’s Happening?

We are a quarter of the way through the 2026 NASCAR Cup Series season and, despite the gears turning on some team’s Silly Season, there are several major Silly Season questions left to answer.

1. Where Does Kyle Busch End Up?

The story of Kyle Busch and Richard Childress Racing seemed like a great turn for the team, and a rebound for the veteran driver upon his signing in 2023. But since his three-win debut season at RCR, things have turned downhill for both Busch and RCR.

Busch is currently on a contract season with the team, and there are several routes for him to go at the end of the year. To many fans, these fall into three main paths: change teams, stay at RCR, or retire.

While retirement seems unlikely, Busch’s options could be limited on the free agent market, all while top RCR prospect Jesse Love continues to knock on the door to the Cup Series garage.

2. Does Jesse Love Stick With RCR?

Speaking of Jesse Love, while he is a great option to take RCR into a new era, rumors from 2025 suggest he could be on the table for a spot at another team.

Last year, amid Legacy Motor Club’s bid to get a third charter for 2026, rumors circled that Love might be an option for the team. While LMC did not get this charter for this season, they will for next season, something that could bring Love’s name back into the picture.

Nonetheless, if Love is forced to decide between the two, given that a spot opens up at RCR, it could be a hard call for the reigning NASCAR O’Reilly Auto Parts Series Champion. LMC has had its struggles in the past, but is improving slowly, all while RCR looks like a team in need of a new coat of paint.

3. What Does HMS do About Alex Bowman?

Alex Bowman has had a trying 2026 season. After tough finishes in the first two races of the season, Bowman missed four races due to a vertigo diagnosis that followed an early exit from his car at Circuit of the Americas.

This stretch, the third time Bowman has missed a significant number of races during his tenure at Hendrick Motorsports, came at a tough time for the 32-year-old, as he is on a contract season with the team. For a time now, most have felt that Bowman was the weak link at Hendrick; however, while that may be the case, he is a reliable option for the team.

The main problem if HMS moved on from Bowman would be who replaces him, as HMS seemingly does not have a realistic option in the early portions of the season.

4. Will Penske Retain Austin Cindric?

Another major name on the potential chopping block is Austin Cindric, who, following another playoff performance in 2025, is facing a contract season in 2026.

Cindric, the son of former Penske executive and current IndyCar team member Tim Cindric, has seen his fair share of questions throughout his time in NASCAR’s top division. While he has yet to look like a real championship contender, he has won races for the team, something that other drivers failed to do at Penske.

Though there may be calls for Penske to move on from Cindric, the fact remains that he is a winner, and a solid option for the team, and much like HMS and Alex Bowman, a suitable replacement for Cindric has yet to be seen.

5. Who Drives for Legacy Motor Club?

By far the biggest question on the minds of fans is who will get the newest full-time, chartered spot in the NASCAR Cup Series garage.

LMC is getting its third charter from Rick Ware Racing, leading many fans to shape this storyline into the addition of another competitive team to the Cup Series field. While LMC may not be the best, they showed tremendous strides towards competitiveness last season.

Early rumors of names for this seat include Riley Herbst, Harrison Burton, and Jesse Love. Each has a compelling argument leading towards their spot with the team, though these are, as of press time, still just rumors.

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