The 2025 NASCAR Cup Series season has been a wild ride, but for 23XI Racing, co-owned by Denny Hamlin and Michael Jordan, it’s been a rollercoaster of courtroom battles and gut punches. The trouble kicked off in fall 2024 when 23XI, alongside Front Row Motorsports, refused to sign NASCAR’s new charter agreement for 2025. Charters guarantee teams a spot in every race and a hefty slice of prize money, but the teams balked at terms they called unfair, especially a clause blocking lawsuits against NASCAR.

Instead of signing, they filed an antitrust lawsuit, accusing the sanctioning body of monopolistic practices that stifle competition and limit team revenue. For a while, it looked like they’d dodge the bullet, but a federal judge granted an injunction in December 2024, letting 23XI and Front Row keep their charters and race as usual while the legal fight played out. But the tide turned in June 2025. The U.S. Court of Appeals for the Fourth Circuit flipped the script, overturning the injunction and opening the door for NASCAR to yank all six charters, three from each team, including two acquired from Stewart-Haas Racing. 23XI’s drivers, Bubba Wallace, Tyler Reddick, and Riley Herbst, now face the uncertainty of racing without guaranteed spots.

The ruling, which takes effect after a 21-day window unless a rehearing is granted, could cost the teams a staggering $270 million in charter value, with a single charter recently sold for $45 million. The financial hit is brutal, and the teams’ fight to keep their charters hinges on a December 1 trial that’s shaping up as a make-or-break moment for their future. The fallout doesn’t stop there. 23XI and Front Row are now “open” teams, forced to qualify on speed and scraping by on less than a third of the prize money that charter teams pocket. A federal judge shot down their bid for a temporary restraining order, noting NASCAR’s pledge not to sell the charters immediately and no imminent risk of missing races like Dover or Indianapolis.

23XI is losing sponsors along with charters

Just when it seemed things couldn’t get worse, 23XI took another hit. DraftKings, the sports betting giant whose logo has been a staple on Bubba Wallace’s No. 23 Toyota since 2021, is jumping ship to Kaulig Racing. The move, announced on August 12, is a seismic shift in NASCAR’s sponsorship landscape. DraftKings, which partnered with 23XI after NASCAR greenlit sportsbook deals in 2020, brought live odds and fan promotions that juiced up race days.

Now, Kaulig Racing, fielding cars for Josh Williams and A.J. Allmendinger, scores the $21 billion betting behemoth as a primary sponsor for Ty Dillon’s No. 10 Chevrolet at Gateway on August 12th and Kansas on September 28th. “I am passionate about delivering fans the best experience possible, which is why it is so exciting to be working alongside DraftKings. It’s an iconic brand that’s become synonymous with innovation and fan engagement, offering a responsible and entertaining way for fans to get even more invested in the action.” Dillon said.

For Kaulig, this is a coup. The team’s been building its brand since going full-time in 2022, and DraftKings’ backing means flashier fan campaigns, better hospitality, and deeper broadcast integrations. Dillon, sitting 32nd in points with one top-10 finish at EchoPark Speedway, also nabbed second in the DraftKings-sponsored In-Season Challenge. Meanwhile, 23XI’s loss stings extra hard coming off the charter blow. The team’s fight to stay competitive without guaranteed spots or big sponsor bucks is a steep climb, and losing DraftKings’ visibility could shake driver and sponsor confidence as the trial looms.

Legacy Motor Club locks in Pye-Barker.

While 23XI reels, Legacy Motor Club is celebrating a win. On August 12, the team announced that Pye-Barker Fire & Safety, the nation’s largest fire protection and security provider, extended its partnership through 2026. Pye-Barker, which joined Legacy in 2024, will stay on John Hunter Nemechek’s No. 42 Toyota Camry for 14 races, keeping its status as the team’s Official Fire Safety Partner. “We are thrilled to have Pye-Barker Fire & Safety renew for next season,” said co-owner Jimmie Johnson. “John Hunter and the No. 42 team are great representatives of the brand, and our collective goal is to put Pye-Barker back in victory lane.”

“This partnership with LEGACY MOTOR CLUB reflects the same values that guide our business every day, putting people first and building lasting relationships built on trust,” said Pye-Barker CEO Bart Procto.  Pye-Barker’s growth, landing on the Inc. 5000 list for fast-growing companies, aligns with Legacy’s push for on- and off-track success, including expanded hospitality and community outreach.

The contrast is stark. 23XI’s charter and sponsor woes threaten its 2025 campaign, with Hamlin’s squad fighting to keep drivers like Wallace and Reddick, whose contracts reportedly demand charter entries. The December trial could redefine NASCAR’s structure, but for now, 23XI is scrambling to stay afloat. Meanwhile, teams like Kaulig and Legacy are capitalizing on big-name sponsors to build momentum, leaving fans wondering how Hamlin and Jordan will navigate this storm.