The Red Sox missed out on signing rumored targets Pete Alonso and Kyle Schwarber after they agreed to five-year deals with different teams this week.
The Red Sox haven’t signed a free agent to a deal that’s more than three years long in Craig Breslow’s tenure as chief baseball officer. (AP Photo/Charles Krupa)
December 12, 2025 | 2:03 PM
2 minutes to read
The Red Sox were considered to be among the favorites to land top free agents Pete Alonso or Kyle Schwarber entering this week’s Winter Meetings. Instead, they watched the star sluggers sign five-year deals with different teams.
As Boston left Orlando empty-handed in its search to add power to its lineup, one agent thinks he knows why the Red Sox weren’t able to get Alonso or Schwarber.
“They don’t believe in long-term deals,” a “prominent” agent told MassLive’s Sean McAdam.
While the contracts Alonso and Schwarber received might not look like super long-term commitments compared to some of the other top deals across MLB, they’re both longer than any deal Craig Breslow has given a free agent since he became Boston’s chief baseball officer in 2023. They’re also richer in value than any contract the Red Sox have given a free agent in Breslow’s tenure, with Alonso receiving $155 million from the Orioles and Schwarber getting $150 million from the Phillies.
The $90 million contract the Red Sox gave Masataka Yoshida ahead of the 2023 season was the last time they signed a free agent to a deal that was at least five years long. They gave Trevor Story a six-year deal in the prior offseason.
Boston’s exact offers for Alonso and Schwarber are unknown. However, it’s believed that the Red Sox’ offer for Alonso was for fewer years and “significantly” less money than the contract he got from the Orioles, The Boston Globe‘s Tim Healey reported. Boston’s lower offer for Alonso was due to his age, with the Red Sox being wary of signing him to a deal that would take him through his age 35 season, Healey added in his report.
Alonso turned 31 on Sunday.
The Red Sox’ reported stance on not giving free agents long-term deals and being wary of the ages of free agents could seemingly play a role in Alex Bregman’s future in Boston. Bregman, who’ll turn 32 in the first week of the 2026 season, is one of the top free agents available after opting out of his contract.
Bregman’s age also might have come into play when the Red Sox signed him last offseason, when he didn’t agree to a deal until the start of spring training. In fact, he took a shorter deal with the Red Sox (three years, $120 million) than the longer deals he was reportedly being offered by the Astros (six years, $156 million) and Tigers (six years, $171.5 million).
As for the latest on Bregman, re-signing the All-Star third baseman is “clearly” the Red Sox’ top priority at this point, The Boston Globe‘s Pete Abraham reported earlier this week. Bregman’s agent, Scott Boras, has also reached out to the Mariners to say that his client would be interested in joining them, The Seattle Times‘ Adam Jude reported earlier this week.
Now, the Red Sox have been more open to giving long-term deals to some of their own players. They signed All-Star pitcher Garrett Crochet to a six-year, $170 million extension in April. Shortly after, Kristian Campbell got an eight-year, $60 million deal, while Roman Anthony agreed to an eight-year, $130 million extension.
In the cases of Campbell’s and Anthony’s contracts, their deals mostly cover the seasons that they still would’ve been under team control. But Anthony’s contract can reportedly climb up to $230 million depending on his performance.
As for the Red Sox’ finances for the 2026 season, they’re projected salary commitments currently sit at $226 million, per Red Sox Payroll on X. That number is roughly $18 million shy of the first luxury tax threshold and $38 million short of the second luxury tax threshold.
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