The Boston Red Sox offseason woes continue to persist as they lost out on all-star first baseman Pete Alonso to their division rivals the Baltimore Orioles. Alonso has signed a five-year, $155 million contract with the Orioles; the $31 million AAV makes Alonso the highest paid first baseman in MLB history.
This is one of the more frustrating losses on a big-name free agent in recent Sox history. Alonso, on paper, was a perfect fit for Boston: they needed a first baseman, a powerful right-handed bat, and they had the money to spend after shedding Rafael Devers contract last season.
Alonso checked every single box.
No reports have come out yet on whether the Red Sox offered a deal to Alonso or not, but either way, it’s a smudge on the entire Red Sox front office after all of the hullabaloo coming out of the winter meetings that Alonso was at the top of Boston’s list.
Boston has been dubbed “the interest kings” by local media; every single year, we hear reports that they are highly interested in some big name free agent, who ultimately doesn’t sign with the Red Sox.
Frustration Beginning to Arise Following Alonso Signing
There are two big frustrations for Red Sox fans following this deal: first and foremost, Boston was either out-bid, or out-classed by a small market, historically weak franchise in Baltimore. As a big market team with money to spend on anyone Boston missed out on a reasonable deal for a player that would have filled so many needs for the roster.
I wrote this in an article maybe 20 minutes before the deal was announced:
“I think I speak for all Red Sox fans when I say that if Boston loses out on Alonso to the Orioles (the freaking Orioles), all hope will be tossed out the window when it comes to signing big name free agents during the John Henry-Craig Breslow reign in Boston.”
It’s another sign that Red Sox owner John Henry is unwilling to shell out money to help the team he owns. Why he won’t do it is beside the point at this juncture; Red Sox fans are frustrated with Henry’s apparent lack of interest in Boston in lieu of his other assets, Liverpool F.C., the Pittsburgh Penguins, and his quest to expand into the NFL or NBA.
The second frustration is that Alonso signed with a division rival, who the Red Sox will play 13 times in the 2026 regular season. Alonso will almost assuredly be booed into oblivion the second he steps to home plate at Fenway Park the first time the teams meet in Boston in the upcoming season.
Power Bat Still a Need For Boston
Now that Alonso and Kyle Schwarber are off the big board, while trade talks have stalled around Corey Seager, Boston absolutely must make re-signing Alex Bregman a priority.
It’s too late for “maybe this guy is a better fit in Boston” or “maybe we can get player x on a better deal.” No, Boston needs Bregman back in the lineup, because without him, they’ll be banking on second-year player Roman Anthony, aging Trevor Story, and forever injured Triston Casas to provide that thump.
None of those names are entirely trustworthy in the 2026 season, so getting Bregman back is now priority No. 1 for Boston.
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