October 12, 2025
The Boston Red Sox finally returned to the postseason this year, snapping a three-year drought and winning their first playoff game since 2021. But their October run ended quickly, falling to the New York Yankees in the Wild Card series — and now, big offseason questions loom.
One major concern: first base.
After Triston Casas suffered a season-ending injury, the position became a revolving door in 2025, and Boston never found a reliable replacement. Chief baseball officer Craig Breslow has made it clear that stabilizing the infield corner will be one of the club’s top priorities this winter.
Alonso, Diaz, or Naylor?
The Red Sox are expected to explore both trade and free-agent markets. Yandy Díaz of the Rays could be an intriguing trade option, while free agency offers star names like Pete Alonso and Josh Naylor.
On paper, Alonso is the marquee bat. But his reported contract demands could make him a risky investment.
According to Mike Puma of the New York Post, Alonso will seek a seven-year deal in free agency. For the 30-year-old slugger — who will turn 31 before Opening Day 2026 — that would mean a contract carrying him through his age-37 season.
While Alonso remains one of baseball’s premier power hitters, concerns about his long-term durability and limited defensive range make a deal of that length problematic.
“He’s a great hitter, but that kind of term doesn’t make sense for Boston,” one AL executive told The Athletic. “You’re paying for the decline years at that point.”
Alonso’s game is built almost entirely on power. He’s one of the weakest baserunners in the league and ranks below average defensively at first base. That profile projects him as a designated hitter within two or three years — a risky investment on a seven-year commitment.
If the market for Alonso softens to a two- or three-year range, Boston could re-enter the discussion. Otherwise, the Red Sox are expected to pivot toward younger, more versatile options who better fit their long-term plan around Garrett Crochet and Alex Bregman.
