Red Sox Must Stockpile Starting Pitchers at Winter Meetings

The Boston Red Sox roll into the 2025 Winter Meetings in a spot they haven’t seen in ages. They’ve got surplus starting pitching and the wiggle room to actually reshape the roster around it.

With nine legit starters and enough payroll space to chase impact bats, Boston’s making it clear: this winter is about turning depth into real difference-makers. They want to push the club back into true World Series conversations.

Red Sox Rotation Depth Creates Real Trade Leverage

The rotation is front and center for Boston. With Sonny Gray and Johan Oviedo now in the mix, the Red Sox suddenly have one of the deepest starting staffs in the American League.

Not long ago, they were scrambling for back-end innings. Now? They’re staring at a genuine surplus.

Heading into spring training, Boston expects nine experienced starters to be healthy and ready. Guys like Garrett Crochet, Brayan Bello, and Kyle Harrison are all in the mix.

That kind of volume has, unsurprisingly, drawn plenty of calls from pitching-hungry teams. Boston’s become a natural hub for trade talks this winter.

From Depth to Deals: A New Approach in Boston

Chief Baseball Officer Craig Breslow has said it outright: the Red Sox plan to use their pitching depth as trade currency. Instead of just hoarding arms, the front office wants to reallocate resources, especially to the middle of the batting order.

The message is pretty direct. The Sox aren’t just collecting starters—they’re ready to move the right one if it lands them a true impact hitter.

Middle-of-the-Order Power Is the Top Priority

Boston’s biggest need this winter is obvious: a real power threat for the middle of the lineup. The current group has plenty of useful pieces, but they’re missing that consistent, game-changing slugger who makes pitchers sweat and stretches the order.

Breslow and his crew are chasing that fix through every path: trades, free agency, even some creative combos.

Free-Agent Targets: Bregman, Alonso, Schwarber

Gray and Oviedo together cost about $23 million for 2025, which is totally manageable for a big-market club. That leaves Boston with room to chase top-shelf free agents like:

Any one of these hitters would instantly change the Red Sox’s offensive profile and raise their ceiling.

Trade Market Targets: Ketel Marte and Tarik Skubal

The Sox aren’t stopping at free agency. They’re also poking around the trade market, looking at both bats and arms as they try to balance now and the future.

Arizona’s Ketel Marte has come up—a star-level second baseman with real offensive impact and positional value.

Marte, Skubal, and the Balancing Act

Boston’s checked in on Marte, but they don’t sound as aggressive as some other teams. The Diamondbacks want a lot, and the Sox seem cautious about moving too many premium pieces.

On the pitching front, they’re not ruling out upgrades even with all that depth. Trade talks have included names like Tarik Skubal, one of the most electric lefties in the game. Boston’s not settling for “deep”—they’re at least considering ways to get truly dominant at the top of the rotation.

Valuing Duran and Abreu: No Fire Sale in the Outfield

Boston’s open to dealing from their pitching surplus, but they’re a lot more careful with certain position players. Outfielders Jarren Duran and Wilyer Abreu have become real trade chips, drawing steady interest around the league.

Still, the Sox have set a high bar for moving either guy. They know what they’ve got—both have made a real impact on offense and defense lately.

Why the Sox Are Holding Firm

Duran brings speed, better on-base skills, and a spark that can flip games with his energy. Abreu’s got power, plate discipline, and reliable defense that’s tough to find at a decent price.

If Boston moves one—or both—it’d have to be for a blockbuster, not just a minor upgrade. They want to be aggressive, sure, but there’s no appetite for reckless moves here.

Ownership Commitment and the Bigger Picture

Red Sox ownership keeps talking about how they’re willing to invest—not just money, but also prospects and current big-league talent. They’re not satisfied with just small steps forward.

This offseason, Boston walks in with a deep rotation and some real financial flexibility. The front office seems ready to get creative and aggressive if that’s what it takes.

Maybe they’ll chase a big bat. Maybe it’s a blockbuster trade, or maybe they’ll just keep stacking smart moves. However it shakes out, the Red Sox are setting themselves up to leave the Winter Meetings in a stronger spot, with their sights set firmly on the World Series—and, honestly, who wouldn’t want to see them become a contender year after year?

 
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