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Ranking the Red Sox's Top 5 Offseason Priorities

Sep 30, 2026; San Diego, California, USA; Chicago Cubs outfielder Seiya Suzuki (27) strikes out in the fifth inning against the San Diego Padres during game two of the Wildcard round for the 2026 MLB Playoffs at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images IMAGN IMAGES via Reuters Connect

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Ranking the Red Sox's Top 5 Offseason Priorities

Originally posted on Boston Red Sox on SI
By Jackson Roberts | Last updated Oct 13, 2026 10:00 AM ET

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It's a pressure-packed offseason for the Boston Red Sox, and we're here to cover all the bases.

Not many fan bases leave the winter feeling like their team aced the test, and that's going to be less common than ever with the lockout disrupting business as usual this year. So for Boston to maximize its chances of winning next year, priorities must be set.

So which objectives are the most important this winter, and which are only somewhat important? Here's a somewhat definitive list.

5. Bring back Sonny Gray without overcommitting

The Red Sox and Gray have a $30 million mutual option for the upcoming season, and there's a case to be made that such a contract works out for both parties involved. But in the likely event that either side declines the option, a reunion still makes sense.

But if Gray is commanding a three-year deal on the open market, there's also a point at which the Red Sox should walk away from the negotiating table, and potentially even pivot to other options on the market. This roster is quickly getting expensive, and putting a high-dollar deal on the books after 2027 seems risky.

4. Preserve farm system depth wherever possible

The Red Sox have spent the last few offseasons and trade deadlines trying to improve the major league roster at all costs. Admirable, but also somewhat unsustainable.

Beyond keeping No. 1 prospect Franklin Arias, the Red Sox should have a solid list of untouchables this winter, and they should also prioritize free agency for once, rather than looking to the trade market to solve all their roster holes again.

3. Extend Adley Rutschman – or have a really good backup plan

The language coming out of the Red Sox's camp thus far hasn't portended well for an extension between the team and Adley Rutschman. But there's also a history of extensions happening out of the blue in recent years, like those for Garrett Crochet and Roman Anthony.

Boston couldn't have been thrilled about Rutschman's production in the final two months after the trade, but with one year left on his contract and not many attractive options to take over the catching role if he departs, it's time to put a plan in motion — perhaps multiple plans.

2. Resolve the Jarren Duran situation/overall outfield logjam

It's hard to envision a scenario in which Jarren Duran returns to the Red Sox, and the roster functions in perfect harmony.

Boston's outfield has been overcrowded since Anthony debuted in the majors last summer, and Duran wasn't only bad this year, but his presence boxes out the potential to add a big bat to the outfield/designated hitter picture. Which also leads to the top priority for this winter...

1. Add a serious threat to the middle of the order

Randy Arozarena. Seiya Suzuki. Hunter Goodman. A bat in this tier of sluggers is crucial to the Red Sox being able to tout this winter as a success.

Looking around the postseason, it's clear that teams that survive deep into October have multiple scary bats who can feed off each other in big moments. The Red Sox had no one to run alongside Willson Contreras in the playoffs this year, and that needs to change, pronto.

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

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