Red Sox can no longer avoid this painful trade deadline realization

The Boston Red Sox just went through a crucial stretch in their schedule in which they only could muster one win over their last six games. Boston was swept by the Los Angels Angels, whom they now trail in the AL Wild Card standings, and followed that series by losing two of three to the divsion rival Toronto Blue Jays.

This stretch was the perfect opportunity for the Red Sox to prove that they have what it takes to be postseason contenders. Instead, they did the opposite. These struggles now open the door for some tough trade deadline conversations, especially following the promise of Craig Breslow that the team will be looking to make moves to improve the 2025 roster. The cold, hard truth is they cannot wait until the deadline to make a move, or they need to change the path of the organization moving forward.

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Boston needs to act now or decide to sell at the trade deadline

If the Red Sox wait any longer to make a move, it may be too late to salvage the 2025 season. The last six games were a golden opportunity to make up ground in both the AL East division race and Wild Card race.

Having to play in one of the most competitive divisions in all of Major League Baseball is certainly not doing the Red Sox any favors, and after trading away Rafael Devers, Boston has seemed to struggle quite a bit. When they signed Alex Bregman this offseason, Boston expected to pair his power bat in the middle of the order with Devers to create a deadly tandem. Now that this is no longer the case, it may not be too far-fetched for Boston to listen to offers to trade Bregman by the deadline and start building for the future.

Boston fans are growing impatient, and they will be furious to miss the postseason yet again. But if major moves are not made in the near future, the Red Sox could be sealing their fate as a .500 or worse ball club for years to come. Bregman's current contract is techincally for three years but he has an opt-out clause after both the 2025 and 2026 season. If Boston feels like the veteran will likely opt out at season's end, he could be playing for another team the second half of the season.

This is far from what Red Sox fans want to hear, but looking to rebuild may not be the worst idea right now. Even household names do not promise October baseball in Boston, especially when there are so many talented teams they are trying to catch. Breslow can cling to his dream of being a buyer if he wants, but it seems far more likely that this team misses the playoffs entirely than make serious noise come October. The future is still bright, with the Big Three all just beginning their careers and other young, controllable talent in place. But the holes are glaring, and this could be the perfect chance to get them patched ahead of 2026.