3 significant 'what ifs' that could've drastically changed the Red Sox season

It might be a cliché, but the MLB season really is a marathon, not a sprint. The 162 games spanning from late March to September are no joke.

It's fun for fans to check a team’s baseball reference page near the end of the season and see all the players who made an appearance for them. Who remembers Michael Fulmer’s two and two-thirds innings for the Sox back on April 14, or the eight games Blake Sabol was Boston’s backup catcher?

Another fun thing to do with such a long season is playing the 'what-if' game, and the 2025 Red Sox season is full of good ones. There have been a myriad of injuries that have affected the season, another poorly executed trade deadline, and some players that didn’t live up to expectations. Here are the biggest 'what-ifs' of the Red Sox season. 

3 significant 'what ifs' that could've drastically changed the Red Sox season

What if Triston Casas never got injured?

This has to be the biggest what-if of the season. While Triston Casas struggled mightily through the first month of the campaign, his injury was the tipping point in the Rafael Devers drama. Had Casas not ruptured a patellar tendon, Raffy wouldn’t have been asked to move to first base after already being upset about being moved off of third base.

In Devers' first (and only) season as a full-time DH, he racked up 2.2 bWAR in 73 games. Despite all the drama surrounding him, his play at the plate never faltered, but his attitude with the coaching staff and front office wasn’t working, and they felt the need to trade him.

Had none of that happened, Devers would have been on pace for a 4.9 WAR season. Not only did they miss out on a projected 2.7 WAR, Jordan Hicks has been worth -1.1 bWAR in Boston. While Kyle Harrison’s Sox debut got him 0.2, that is still a 3.6 WAR swing that the trade has caused to this point in the season. Boston sent another piece of the trade, James Tibbs, to the Dodgers in the catastrophic Dustin May deal. Who knows if they make that trade without Tibbs? If Casas never fell injured, Devers might still be in Boston, and Hicks, Harrison, and May likely wouldn't be. 

What if Boston traded for Joe Ryan at the trade deadline?

This was the big swing the Sox took at the deadline, but it ended up a whiff. While reports after the fact were that the Twins were never truly playing ball and were just stringing Craig Breslow and the rest of the front office along, what if they were actually able to agree to terms?

Boston’s rotation would look completely different right now. There would be an established one through four of Garrett Crochet, Ryan, Brayan Bello, and Lucas Giolito. Payton Tolle likely wouldn’t have been summoned for his MLB debut, not just because they wouldn’t have needed to call him up, but he likely would have been part of the return for Ryan. Reports were that the Sox were offering two of their top three prospects at the time, Tolle, Jhostnyxon Garcia, and Franklin Arias.

What if Trevor Story wasn’t the worst hitter in baseball in May?

Trevor Story has been a hero of the Red Sox's season. In his first fully healthy season in Boston, the shortstop might reach 30 homers and 30 stolen bases, will likely have over 100 RBIs, and be a 4-WAR player for the first time in a Red Sox jersey. That is all the more impressive when adding in the fact that he had a horrendous May. 

In May, Story hit just .158 with an OPS under .450. He had just three extra-base hits and seven RBIs. The result of that was the Sox's worst month of the season, too; they went 11-17.

What if Story wasn't terrible, but just below average, a batting average around .200 and an OPS around .600? That could have resulted in three or four more wins. While that doesn’t seem like many, that’s the difference between the Wild Card and leading the division, or even the American League. The AL is so tight with just weeks to go. If Story didn't sputter for an entire month, would the Red Sox be leading the league right now?