As the Milwaukee Brewers celebrated their first-ever World Series championship on the Tampa Bay Rays’ home turf at Tropicana Field on Wednesday night, the sense of finality that always accompanies the final out of the postseason felt more intense than usual.

With Major League Baseball’s collective bargaining agreement with its players’ union set to expire on December 1, most league insiders expect this off-season to extend well beyond pitchers and catchers’ typical reporting date for spring training in mid-February. In fact, as players and team owners dig in their heels for their most contentious battle since the strike that canceled the 1994 World Series, a labor stoppage is seen as all but guaranteed—the only question is whether it will wipe out some or all of the 2027 season.

Team owners are insistent on implementing a salary cap, similar to the systems in the NBA, the NFL and the NHL that restrict club payrolls and in some cases individual players’ compensation—a concept that the MLB union has long viewed as a deal-breaker. Owners have not seriously put the issue on the table since the 1994-95 strike, when they attempted to impose a salary cap unilaterally and begin the 1995 season with replacement players in an effort that was stymied by the National Labor Relations Board and then-federal district judge Sonia Sotomayor.

Now, owners and commissioner Rob Manfred say a cap is needed to level the playing field between big-market, free-spending clubs like the Los Angeles Dodgers and smaller-market rivals shelling out less than a quarter as much for their rosters. But there is another financial motivation behind MLB’s renewed push: Investment bankers believe that a salary cap, combined with more equitable revenue-sharing rules, would significantly boost team values for a league that has largely been left behind by its peers in basketball and football.

And with much more money at stake than in the labor battle three decades ago, owners aren’t expected to back down easily.

“If you lose a season and the CBA is positive for the owners, I think asset values will continue to go up,” says Sal Galatioto, president of Galatioto Sports Partners. “If you lose a season and you come out with basically the same economic system you have now, then the owners are going to take a........

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