The Boston Red Sox have stood out in a slow 2025-26 offseason, as they've made 10 trades to shore up their roster before the new year (subscription required). Boston has traded from its deep pool of top pitching prospects and lower-rotation big leaguers to add Sonny Gray, Johan Oviedo and Willson Contreras, among some smaller moves.
Gray and Oviedo are strike throwers (Gray ranked among the top in the league during his age-35 season, his last with the St. Louis Cardinals) and Contreras is a consistent bat with a jolt of power and he plays solid defense at first base, a position the Sox have desperately needed filled. Boston's additions have landed it at No. 8 on MLB insider Jon Heyman's list of the 15 biggest winners at the halfway point of the offseason (subscription required).
Heyman noted that the Red Sox could jump up the list with another addition to their batting order. A reunion with Alex Bregman would be the best possible outcome, but he also mentioned Bo Bichette or Ketel Marte as possible infield additions. Boston has expressed interest in those three players, as well as infielder/outfielder Brendan Donovan, yet another Cardinal on the trade block.
It's in the Sox's best interest to add at least one of the above bats — not only because their offense needs more of a lift after Bregman's contract opt out, but because the Baltimore Orioles and Toronto Blue Jays came in at No. 1 and 2, respectively on Heyman's list of offseason winners.
MLB insider Jon Heyman lists Red Sox among offseason's biggest winners so far, behind two AL East rivals
Boston's two division rivals have gone big so far this winter after very different disappointing ends to the 2025 campaign. Even with all its breakout players and former top prospects, Baltimore didn't sniff the postseason and came in last place in the American League East while the Jays fell to the Dodgers in the World Series.
The Orioles' additions of Pete Alonso and Taylor Ward have added plenty of strength to its offense and Toronto's bold signing of Dylan Cease showed just how serious it is about competing in the wake of a loss. The Red Sox need to match their moves with a similarly assertive reunion with Bregman, signing Bichette or trading for Marte. Gray, Oviedo and Contreras are all great players, but adding just one bat after losing Bregman keeps Boston stagnant rather than improving its offense.
Contreras, Bregman and Trevor Story would be a deadly trio of righties at the top of the Sox's order, and they need that level of thump to compete with their rivals, the offseason's biggest winners so far. Boston must add Bregman or a comparable bat to move up Heyman's list and to compete in one of the best divisions in baseball.