After a quick exit in the playoffs, the Boston Red Sox seem ready to shake things up heading into 2026. Offseason moves have already started with the shocking trade for Sonny Gray, and with Alex Bregman opting out of his deal, and outfield logjams putting Jarren Duran squarely in trade-rumor territory, this could be an interesting Winter Meetings.
1. Solve the infield question — Bregman's departure creates a hole.
Bregman opting out leaves a void at the hot corner, uprooting what was supposed to be the veteran anchor of the infield. Boston now has to decide whether to go all in to re-sign him, bring in a proven bat who fits like Pete Alonso, trade for one, or trust a younger core, but this offseason needs to bring clarity before spring training.
2. Clean up the outfield — either solidify or cash in on surplus.
With Duran on the trade block and stack-ups of outfield talent ahead of him, Boston should deal from the surplus for more pitching help. The current four-or-five-man outfield merry-go-round is too fragile to rely on for another playoff push.
3. Add rotation depth — the top of the staff looks ok, the rest doesn’t.
After adding Gray and Johan Oviedo to shore up the top of the rotation, Boston’s still thin behind them. To go 162 strong — and survive a long postseason gauntlet — they need at least one dependable mid-rotation arm and a swingman or two. Without those, the bullpen and rotation workloads look scary.
