Ranking the Red Sox’s most important free agency decisions this offseason

Expectations are high for the Boston Red Sox this offseason as they sit at the cusp of becoming true playoff contenders. 

Entering the All-Star break, the Sox had the chance to sneak into the Wild Card as the Tigers appeared they might be sellers at the deadline and the Royals. But after a late summer slump and AL Central surge, it was clear by mid-September that postseason baseball was unlikely. Fortunately, the Sox have the chance to end the story differently in 2025 and become AL East threats this offseason. 

Boston has several weaknesses it needs to improve; it’s not a matter of what but in what order. With only a few weeks before winter meetings begin in December, the Red Sox must get their priorities straight before they enter free agency negotiations. Here are Boston’s most important free agency decisions this offseason.

Ranking the Red Sox’s most important free agency decisions this offseason

1. Who their ace will be

Signing a No. 1 starter is a non-negotiable. Though Tanner Houck, Brayan Bello, and Kutter Crawford are solid middle-rotation pitchers, and Lucas Giolito and Garrett Whitlock's returns add depth, none can substantially raise the rotation’s floor and ceiling. Adding a player like Corbin Burnes, Max Fried, or Blake Snell, would substantially raise the team’s playoff potential. While Boston’s rotation was serviceable, adding a star starter is critical to taking the Sox to the next level.

2. How to strengthen the bullpen

The Sox bullpen fell apart in the second half of the season. Behind Luis García and Lucas Sims, who were acquired at the trade deadline, the bullpen had a 5.45 ERA after the All-Star break. García and Sims had an 8.22 ERA and a 6.43 ERA, respectively, and not a single save before they got hurt in late August.

Ultimately, relief pitchers held a combined 4.39 ERA and 1.34 WHIP and blew 39 saves, tied for third worst in the league. Boston got a jump start on improving their bullpen by signing lefty Justin Wilson, but they can’t stop there.

3. Which righty bats should join their lineup

The lefty-heavy lineup didn't help the Red Sox as they struggled against left-handed pitching. Sox batters hit below a .250 batting average and struck out a league-high 506 times against southpaws. To make matters worse, Roman Anthony, Marcelo Mayer, and Kyle Teel, three of Boston’s top four prospects, are lefties. That leaves chief baseball officer Craig Breslow no choice but to add at least one righty bat this offseason. 

4. How to improve plate discipline in their lineup

Next year’s lineup needs to put the barrel on the bat more frequently — 1,570 strikeouts and a 28.0% whiff rate won’t get the Sox to the playoffs. Though Boston slugged .423 and had a hard-hit rate of 41%, the lineup lacked consistent contact. While it’s not their most urgent issue, the Red Sox must cut down on swings and misses if they want to play at playoff caliber.

5. Which Gold Glove Award winner would be best to add 

Boston needs to clean up its defense. Rafael Devers and Tyler O’Neil each ranked in the top five for errors committed by their position, contributing to the 115 errors the Sox committed. While Wilyer Abreu had a great year and won a Gold Glove, the rest of the lineup needs to do better to make clean outs. A healthy Trevor Story should help tighten the defense, but it never hurts to have more talent.

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