The Red Sox don’t have a seat in October this year, but they still have plenty to watch. With the postseason down to the Milwaukee Brewers, Tampa Bay Rays and Cleveland Guardians, Boston can already start circling potential free-agent fits for a winter that could shape the roster in a big way.
The biggest needs are clear enough. The Red Sox could use more pop in the middle of the lineup, at least one or two bullpen arms and possibly a starter, depending on what happens with Sonny Gray this winter. That makes the next wave of free agency especially relevant, and a few players still active in October should be on Boston’s radar.
Jackson Bauers has been one of the postseason’s early standouts. The 2026 National League Championship Series Most Valuable Player followed a breakout regular season with a strong October run, and he’s already positioned himself for a healthy payday.
In 144 regular-season games, Bauers hit 26 home runs and drove in 86 runs, then continued supplying offense in the playoffs for Milwaukee. He’s going to cost more than before, but he still figures to be cheaper than names like Randy Arozarena and Seiya Suzuki.
If Boston believes Bauers is more than a one-year surge, he’d be a compelling addition.
Austin Hedges is a different kind of target, but one that could fit a very specific need. If the Red Sox want more competition behind the plate, he makes sense as a backup catcher option.
Hedges turned in a solid 2026 season, batting .247/.325/.377 with six home runs and 25 RBIs across 78 games. The 12-year veteran is an unrestricted free agent, and at the very least he could push Connor Wong for the backup job.
The most ambitious name on the list is Freddy Peralta. He might be more of a dream fit than a realistic one, especially with Boston already carrying plenty of money on the books and facing decisions such as whether to extend Adley Rutschman.
But if Gray departs and the Red Sox decide to spend more heavily on the rotation, Peralta would be the prize. The right-hander is a two-time All-Star with a 3.43 career postseason ERA in 12 games, and he’s been even sharper this October with a 0.79 ERA over 11 1/3 innings.
Boston has already poured resources into its rotation, and Peralta would stand as the best starting-pitching option available this winter.
In Other News...
Red Sox Already Have A Shortstop Decision Looming Over 2027
Trevor Story has given the Red Sox a steadier run at shortstop than the uncertainty around his contract might suggest, but the longer view is already coming into focus. Bostons infield picture is moving toward 2027, and the conversation is beginning to center on whether Story is still the answer there or whether the organization eventually turns to one of its younger options.
Franklin Arias is the name that keeps hovering over that discussion. The prospect has the kind of upside that makes him easy to imagine as a future major league option, even if the path from prospect status to everyday shortstop is still ahead of him. For now, the Red Sox are left weighing performance, roster timing and possible positional shuffling, with the real decision on their 2027 shortstop still unresolved. [Read more 🡒]
Red Sox Just Lost Another Trusted Voice In A Risky Spot
Taylor Smith is headed to Oakland after being hired as the Athletics new president of baseball operations, a move that once again chips away at the Red Sox front office tree. Smith had served as Bostons assistant general manager, and his departure comes on the heels of another familiar loss in the department, with Paul Toboni previously leaving for Washington. It is the kind of personnel churn that does not show up on the field right away, but can reshape an organizations depth behind the scenes.
Jared Banner, another former Red Sox executive, has now also landed a major role with Baltimore as the Orioles new general manager. For Boston, the pattern is hard to miss: trusted voices in baseball operations keep getting poached for larger opportunities elsewhere. The Red Sox have had no shortage of turnover in recent years, but losing multiple familiar evaluators and decision-makers in such a short span is the sort of development that can leave a real imprint on how the next wave of roster calls gets made. [Read more 🡒]
Red Sox Power Search Just Took One Trade Option Off The Board
The Red Sox have been connected to another possible trade target in the search for more offense, but one of the cleaner fits appears to be off the table. Colorado catcher Hunter Goodman had surfaced as a name worth watching because of his upside and team control through 2029, yet Jon Heyman has dismissed Boston as a likely landing spot after the club recently brought in Adley Rutschman.
That leaves the Red Sox looking elsewhere as they continue sorting through power options that better match their current roster needs. Goodman is still the type of player other clubs could covet, but for Boston the more realistic path seems to run through other free agents and trade candidates who fit the lineup and defensive picture more naturally. [Read more 🡒]