Major League Baseball's owners and Players' Union appear headed for a lockout when the current collective bargaining agreement expires on Dec. 1 at 11:59 p.m. ET. Do the latest business dealings by Fenway Sports Group signal that the Boston Red Sox owners are gearing up for a lengthy lockout?

The Los Angeles Dodgers have become baseball's boogeyman after winning back-to-back World Series titles, a sentiment that has only increased after LA landed back-to-back American League Cy Young Award winner Tarik Skubal in a trade deadline deal with the Detroit Tigers. The biggest point of contention between the two sides is the owners' desire to implement a salary cap and floor, a move they argue will allow for greater parity across the league.

Of course, the players are staunchly opposed to a salary cap, especially under the league's current offers, which include maximum contracts similar to those in the NBA, as it greatly limits players' earning power. 

While the two sides will have nearly four months to bridge the gap, neither side seems particularly keen on giving in at this point. "The MLBPA is not going to accept a salary cap; it's just not," said ESPN's Jeff Passan on the 'All The Smoke' Podcast. "And MLB right now, the way it's going, is saying, 'we want a salary cap, and we will not accept anything else,'" he continued. 

While missing games is certainly a worst-case scenario, the players seem willing to do so if it comes down to it. "There's a line that we're not going to cross, and if we have to miss games, we'll miss games," Pittsburgh Pirates' star pitcher Paul Skenes told Colin Beazley of the Pittsburgh Post-Gazette. 

Over the past year, Fenway Sports Group, led by Red Sox principal owner John Henry, has made a number of business moves, including selling shares of its other franchises.

On June 23, the NHL Board of Governors unanimously voted to approve FSG's sale of the Pittsburgh Penguins to the Hoffmann Family of Companies for $1.75 billion. That's a nearly $1 billion increase from the $900 million that the group purchased the team for in 2021. 

On Monday morning, FSG found itself in the news once again, with Sky News reporting that the group had agreed to sell a minority stake in Liverpool FC to a consortium including billionaire Jeff Bezos. 

According to a 2025 Forbes study, Major League Baseball made over $12 billion in the 2024 season, a figure that has almost certainly risen in each of the last two seasons. Whether it be TV deals, merchandise, or game-day-associated revenue (tickets, concessions, etc), the owners risk losing nearly all of their expected revenue. With both sides stuck in a stalemate over the implementation of a salary cap, could Henry and FSG be offsetting the potential losses of a completely canceled 2027 season?

We'll likely never know the true answer; however, their recent dealings certainly seem to signal that there will be at least some amount of games missed during the 2027 season.