The Biggest Silly Season Questions Entering 2026

MARTINSVILLE, VIRGINIA - MARCH 29: Alex Bowman, driver of the #48 Ally Chevrolet, and Tyler Reddick, driver of the #45 Mobil 1/O'Reilly Auto Parts Toyota, drive during practice for the NASCAR Cup Series Cook Out 400 at Martinsville Speedway on March 29, 2025 in Martinsville, Virginia. (Photo by Logan Riely/Getty Images)
Photo by Logan Riely/Getty Images

What’s Happening?

Though the 2026 NASCAR season has yet to start, the 2027 Silly Season talk is already picking up. So, what are some major storylines to watch entering the 2026 NASCAR season?

Who Retires?

NASCAR saw many top drivers call it a career in the latter half of the 2010s, and like clockwork, there is already another batch of veterans that could be looking to hang up the helmet in the near future.

On this list are some drivers that are in very stable situations, like 41-year-old Michael McDowell, who is just entering his second full-time season at Spire Motorsports, or 44-year-old A.J. Allmendinger, who seemingly has a spot at Kaulig Racing as long as he wants it.

Both of these drivers still can win races, but both are in the midst of multi-year losing streaks, having not won a race since the 2023 season.

Other options that make the rounds of conversation in the fan community include 41-year-old Brad Keselowski, who has yet to show signs of true competitiveness as a driver/owner, and 45-year-old Denny Hamlin, who, despite a recent renewal with Joe Gibbs Racing, hasn’t shied away from the fact that his career is coming to an end.

Regardless, the biggest question of all is Kyle Busch, who is entering his fourth full-time season as a driver for Richard Childress Racing. Busch is on a contract year, and though he finds the front of the field often, with prospects like Jesse Love waiting in the wings, Busch could enter the offseason in a tight spot.

Who Moves?

Kyle Busch is far from the only driver on a contract year in 2026, with Bob Pockrass of FOX Sports reporting last week that the number of drivers facing the end of their contract this year is over 20.

Entering the new year, there were a few names that fans knew were on a contract year, such as Austin Cindric, or most importantly of all, Kyle Larson, who is coming to the end of his extension signed in 2022.

Larson is expected to re-sign, but the biggest story of the past two weeks is perhaps Alex Bowman and Tyler Reddick, whom Pockrass claimed in his January 26 report are both on the final year of their current deal.

While Bowman could be racing for his seat in a crowded free agent field, Reddick, should he maintain his consistent nature on track, could be one of the hottest names on the market for teams with an open spot.

Who Is Legacy Motor Club’s Newest Driver?

Last season, 23XI Racing and Front Row Motorsports weren’t the only teams in court, as Legacy Motor Club, owned by NASCAR Hall of Famer Jimmie Johnson, and Rick Ware Racing, took a spat over a charter sale to court.

The battle was regarding a charter that RWR was selling to LMC, a sale that LMC claimed RWR attempted to back out of. In mid-September, the two sides settled, with LMC getting its charter for the 2027 season.

This acquisition opens up another major seat in the NASCAR Cup Series field, and the candidates for this ride could play a major role in LMC’s continued growth.

There were rumors in 2025 that eventual NASCAR Xfinity Series Champion Jesse Love was looking to make the jump to Cup, with LMC an option. While Love could have been looking to make this jump, it’s hard to think that RCR would let him walk after his title win in 2025.

Sam Mayer is another name that often comes to mind when there is talk of a promotion. Last year, Mayer showed he was a real consistent threat for the title, though many have suggested they’d like to see him clean up his racing before making the move to Cup.

Of course, there will always be talk of top Toyota prospects in the mix.

If 23XI ends up with no open spots for the new year, could Corey Heim make the jump to full-time action with LMC in 2027?

What about Brent Crews? The 17-year-old is slated to race in a majority of NASCAR O’Reilly Auto Parts Series races for Joe Gibbs Racing in 2026, and with Denny Hamlin’s long-term future in the air, what if the team opts to promote Crews to the next level if he performs in the OAP Series this year, in preparation for a move to JGR down the line?

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