In 2024, the Cup Series’ Silly Season began with a harmless shift of drivers and is ending with a courtroom battle. The updates took a wild turn when Tony Stewart announced his team would shutter. 70-time Cup race-winning Stewart-Haas Racing’s demise brought out the faults of NASCAR’s system as well, which can axe even the most successful teams. Now, Stewart may not even scrape the last profits of his crumbling team with Michael Jordan’s fight growing intense.

After NASCAR dropped a new charter deal with a short 6-hour window to sign it, teams were left in a fix. 13 teams signed it, reportedly claiming later that they feared their charters would get absolved. Only 23XI Racing and Front Row Motorsports stood out, beginning a legendary battle with the sport. However, they may fail to keep promises made to Stewart.

Tony Stewart’s profits in jeopardy

After SHR’s impending demise became public in May, alerts sounded across the Cup Series garage. Charter value was the hot topic, as teams fumbled to strike deals with Tony Stewart to secure his charters. Rumors circulated about three potential teams – FRM, 23XI Racing, and Trackhouse Racing. FRM publicly announced its purchase in May, while Michael Jordan’s team still speculated. However, the NASCAR lawsuit revealed that even 23XI Racing “entered into a purchase agreement on August 7, 2024.” But both recalcitrant teams have one common factor – “the transaction is still in escrow and requires approval from NASCAR.”

Now, with things heating up inside the courtroom, Michael Jordan is also not proceeding with the purchase. NASCAR’s approval of the charter purchase would first require the team to request for it. But with legal matters occupying the teams’ attention, neither 23XI nor FRM are working towards Tony Stewart’s peace. Bob Pockrass updated the situation: “NASCAR just filed response to preliminary injunction motion. Some quick notes: -New charter deal is 7 yrs ww/possible extension. -Neither 23XI nor FRM has submitted a request yet for a charter transfer from SHR. -NASCAR plans for a season with 32 charters and eight open positions.”

With the charter figures climate uncertain, Tony Stewart‘s prospects seem more dire. For instance, Furniture Row Racing departed and sold its charter to Spire Motorsports for just $6 million. But only five years later, Spire bought another charter, this time from Live Fast Motorsports reportedly for $40 Million. Whispers inside the garage suggested that SHR’s charters would fetch figures in the neighborhood of $25 Million. But 23XI Racing’s strong battle to take down the entire charter system darkens that prospect. Denny Hamlin claimed earlier in May, “The charter agreement needs to be better than what it is certainly before I invest any more money in it.”

And even most of the Cup Series garage is siding with Hamlin and Jordan’s battle.

Winds of change are here

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Since 1949, NASCAR has been a sport based on independent contractors investing their own money for the privilege of racing. However, the racing events and the racetracks were largely owned by the France family. Their monopolistic rule led to some questionable outcomes. Even the most successful teams (like Tony Stewart’s team in the present day) and drivers left the sport with thin wallets. In 1999, Ricky Rudd, who has been elected to the 2025 NASCAR Hall of Fame batch, auctioned off his life’s work for pennies on the dollar. Six stellar years as a driver/owner that saw a Brickyard 400 win came to nothing. Rudd watched his cars and equipment be picked apart and hauled off like junk scraps.

So Michael Jordan and Co.’s drive to revolutionize the sport is gaining traction among other teams. Hendrick Motorsports driver William Byron is hopeful to reverse Rudd’s situation. “I’d like to see our sport be more prosperous. In watching other professional sports and where we could be, I am excited for that. So hopefully that comes to fruition.” His teammate Kyle Larson chimed in, “Obviously, we would love to see it trend upward instead of the opposite. But the teams probably have to make a lot more money to make it viable to pay the people who are working for their organizations.” Even Team Penske star Joey Logano is optimistic about the lawsuit. “This is huge for our sport no matter what happens. It’s obviously big because we’ve never seen it before.”

Evidently, Michael Jordan and his compatriots are on a mission. Even if it means jeopardizing Tony Stewart’s end of the deal, they are determined to change NASCAR.