After their brief return to the postseason in 2025, the Boston Red Sox are expected to be one of the most active teams this offseason. They have money to spend in free agency after the Rafael Devers trade and they have a deep farm system of prospects to flex on the trade market.
It's hard to estimate Boston's exact offseason plan because its spending in the last half decade hasn't exactly reflected a desire to compete for championships. Chief baseball officer Craig Breslow has helped the team take steps in the right direction in 2025 by signing Alex Bregman and trading for Garrett Crochet, but it's been quite some time since the Red Sox signed someone to a megadeal from the free agent market, which is what Bregman, Pete Alonso or Kyle Schwarber would demand.
Some optimistic reporters and insiders think the Sox might pursue two top-tier bats — for example, both Bregman and Alonso — to shore up their offense. Breslow didn't rule out such a plan. Red Sox reporter Alex Speier of The Boston Globe and NESN's "310 to Left" podcast isn't so convinced.
"My suspicion is that they wouldn't do two of the premium bats this offseason. I think, particularly if you're getting into the so-called 'long-term risk' pool, I think that would be hard," Speier said on the November 20 episode of the podcast. "I think there would be room for there to be a reasonably-aggressive second play. Now, whether or not that gets up to the level of Eugenio Suárez, I don't know."
Red Sox insider shoots down chance of Boston signing two top-tier bats this offseason
This perspective contrasts with a report Speier made for The Boston Globe two days prior (subscription required). The insider noted that the Red Sox payroll sits $40 million below the first luxury tax threshold after their first set of offseason roster moves. Boston spent $5 million above the CBT threshold last year and paid $1 million in penalties, and it's expected to spend more this winter. Speier even theorized that the Sox could elevate their spending to up to $20 million over the CBT, as they did when they won the 2018 World Series.
Personally, Speier seems less confident that the Sox will go all-in on two top bats and imagines a Jorge Polanco-type player as the second free agent offensive addtion. This is a troubling development since Boston could lose Bregman and a solid outfield — either Jarren Duran or Wilyer Abreu — this winter. It will need two top bats to improve upon last year's team after those losses.
Most guesses at the Red Sox's offseason plan include reinforcing the offense on the free agent market and trading for a top-tier pitcher. Maybe they go a different direction and sign a top-tier bat and a pitcher, and trade for a complementary bat. But if they sign anything less than two elite players from the free agent market, all the smoke about increased spending will have been false... again.
Speier's questioning of the Red Sox's motivation to spend big is far from ideal. Boston's young core is on lock for years to come (Roman Anthony, Brayan Bello, Garrett Crochet, Ceddanne Rafeala and Kristian Campbell are all on long-term deals) and its competitive window is wide open. The Red Sox are just a few big-market moves away from a long playoff run, but the moves will need to be risky to compete with the Blue Jays and Yankees, division rivals who made it to the World Series in consecutive years.