After a postseason that left the Boston Red Sox searching for answers at the plate, it’s no mystery where the attention has to go this winter: offense first.
Boston has holes on both sides of the roster, but the bat side feels like the one that has to get addressed with urgency. There are different ways to do it, too. A trade is very much in play, and the Red Sox have enough farm system pieces to at least make other teams listen if the return is the right one.
One name that has surfaced as a possible target is Jeremy Pena.
Bleacher Report recently floated Pena as a player who could make sense for Boston, and the fit is easy to see. He’s a World Series MVP, a one-time All-Star, and he isn’t set to hit free agency until 2028.
“The moment Peña hired Scott Boras as his new agent in June 2025, the likelihood of a long-term extension prior to hitting the open market shrank considerably for the Astros.
“A wide-open AL West ultimately convinced the Astros to steer away from selling at the deadline, and even if they do view themselves as contenders in 2027, flipping Peña before losing him in free agency could still be on the table,” Bleacher Report wrote.
Pena’s most recent season might not have gotten enough attention, but the numbers were strong: a 124 OPS+, an .802 OPS and 22 home runs, which matched the most he has hit in a season.
For Boston, the appeal is obvious. A right-handed bat with that kind of pop would fit right into what the Red Sox need to add.
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Red Sox Offseason Gamble Produced One Huge Win And One Costly Miss
The Red Sox went into the offseason leaning on trades to reshape the roster for 2026, and one of those swings delivered exactly what they hoped for. Contreras arrived in the deal that sent Hunter Dobbins and pitching prospects away, and he immediately became more than just a new name on the roster, putting together a strong season, setting career highs and bringing a steadying presence to the clubhouse.
The other move told a different story. Bostons deal for Oviedo never really took off in 2026, with his role limited enough that the return felt thin compared with the cost. He remains under team control for 2027, which at least gives the Red Sox another chance to get value from the transaction, but the clock is already ticking before he reaches free agency after that. [Read more 🡒]
Former Red Sox Infielder Is Making Boston's October Regret Harder To Ignore
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Hamilton turned in one of his most important games of the postseason by collecting two hits, scoring three runs and stealing two bases in Milwaukees 7-4 victory. Across the season, he has also offered a steady blend of contact and disruption with a .245 average, 13 doubles, three triples, four homers, 26 RBI and 30 steals in 121 games, the kind of production that can leave a former club wondering what it might have had. [Read more 🡒]
Red Sox Suddenly Face A Real Jarren Duran Trade Question
Jarren Duran has become one of the more interesting names to watch on the Red Sox roster this winter, not because Boston has said it wants to move him, but because rival speculation keeps circling back to him as a possible trade chip. Bleacher Reports Zachary D. Rymer floated a scenario in which the Phillies would send right-hander Orion Kerkering to Boston for Duran, a deal that would give Philadelphia a boost in the outfield while testing how much appeal Duran still carries after a season in which he struggled.
For the Red Sox, the question is less about whether Duran still has value and more about what kind of value they think he brings compared with the return. Kerkering would fit a very different need, and the idea underscores how Bostons outfield picture could remain part of the roster conversation rather than a settled piece. It is only a hypothetical for now, but it is the sort of discussion that tends to stick when a players name starts showing up in trade talk. [Read more 🡒]