The Boston Red Sox should be paying close attention to the Major League Baseball postseason right now, despite the fact that they aren't playing in it themselves.
The Red Sox could use some more power in the middle of the order, one or two bullpen arms and maybe even a starting pitcher, depending on what happens with Sonny Gray this winter. There are just three teams left alive in the postseason right now in the Milwaukee Brewers, Tampa Bay Rays and the Cleveland Guardians.
Once the postseason comes to an end, free agency will begin and that should be big for Boston and there are a few options heading to the open market that should intrigue the Red Sox who are still playing right now.
Jake Bauers — Milwaukee Brewers
Bauers has been among the stars of the postseason so far. The 2026 National League Championship Series Most Valuable Player had a breakout 2026 campaign and it has carried over into the playoffs. Bauers hit 26 home runs and drove in 86 runs in 144 games in the regular season. He has powered Milwaukee's offense in the playoffs as well. Bauers has earned himself a nice payday this winter, but he'll surely be cheaper than guys like Randy Arozarena and Seiya Suzuki. If the Red Sox think Bauers is more than a one-year wonder, he'd be an intriguing addition this winter.
Austin Hedges — Cleveland Guardians
If the Red Sox want to add competition for the backup catcher spot, Hedges is someone who could make a lot of sense. He had a solid 2026 season. Hedges slashed .247/.325/.377 with six home runs and 25 RBIs in 78 games played. Hedges is a 12-year big league veteran and will be an unrestricted free agent. At the very least, he'd be competition for Connor Wong.
Freddy Peralta — Tampa Bay Rays
Peralta may be more of a dream target right now than a realistic one. The Red Sox already have plenty of money on the books and decisions to make, like whether or not to extend Adley Rutschman. But if the Red Sox were to lose Gray and want to invest more in the starting rotation, Peralta is the guy. The righty is a gamer. He is a two-time All-Star with a 3.43 career postseason ERA in 12 games. He has a 0.79 ERA in 11 1/3 innings pitched in the 2026 playoffs. The Red Sox have invested in the rotation multiple times. Peralta would be the best option this winter.
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