What a Successful Red Sox Offseason Actually Looks Like

Aug 26, 2026; Miami, Florida, USA; Boston Red Sox pitcher Sonny Gray (54) delivers a pitch against the Miami Marlins during the first inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images IMAGN IMAGES via Reuters Connect

What a Successful Red Sox Offseason Actually Looks Like

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Oct 3, 2026 3:27 PM ET

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Whether this season was a success or a failure for the Boston Red Sox is up for debate. That they have work to do this winter is not.

After an 87-win season that was miserable for four months and awesome for two, the Red Sox showed all their flaws during their two-game series loss to the New York Yankees earlier this week. Boston is watching two division rivals keep playing in the playoffs post-elimination for the fifth year in a row.

The way the Red Sox lost was demoralizing, as the offense put up the lamest fight we've seen from a playoff team since the 2020 Cincinnati Reds. Here is a concrete blueprint for this team to move forward, lest it suffer a similar fate next fall.

1. Bring in an impact middle-of-the-order bat

There are some options here. Randy Arozarena might be the most exciting name in free agency, but Seiya Suzuki is a fun one as well. Even Yandy Díaz could be a nice get. What matters is bringing in someone who can compliment Willson Contreras in the middle of the order.

It's tough to count on Adley Rutschman, Wilyer Abreu, Ceddanne Rafaela, or Roman Anthony to light up the scoreboard in the postseason based on what we've seen throughout their careers. If the Red Sox want to be true contenders, they need someone else to fear.

2. Adequately fill Sonny Gray's spot in the rotation

We don't know if Gray is coming back to the Red Sox, though it seems a safe bet that it won't be on his $30 million mutual option. In fact, we don't know if Gray is continuing his major league career at all.

What we do know is that if the Red Sox go into next season without a pitcher of similar pedigree to Gray, their rotation is in major danger of taking a step back. The 36-year-old put together a vintage performance, tying for the major league lead in wins while pitching to a 2.76 ERA. That's a huge reason why the Red Sox got to make the short appearance they had in the postseason.

3. End the awkwardness with Jarren Duran

The longer Duran stays on this roster, the tougher it gets to fill out a lineup card on any given day. It's no longer viable to have one of the core outfielders in the designated hitter slot when you sign or trade for another big bat. And whether you've loved Duran or hated him all along, you'd have to admit that the situation seems to have run its course.

If Duran is on the opening day roster, whenever opening day might be post-lockout, it will be a real surprise.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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