4 Red Sox Veterans Who Aren’t Locks for 2026 Playoff Roster

The Boston Red Sox's magic number to clinch a postseason berth is down to three and we should see the club get over the hump in the next few days.

Now, of course, Boston hasn't been red-hot recently, to say the least. The offense has been sputtering and they had a scare on Thursday as Willson Contreras was forced to leave early after getting hit on the hand by a pitch. But the Red Sox got back in the win column and they could clinch a postseason spot as soon as this weekend.

When the playoffs arrive on Sep. 29, there will be some difficult decisions for Boston to make as it determines its roster for the three-game Wild Card round series. On Sep. 1, rosters expand across baseball from 26 to 28. But in the playoffs, it goes back down to 26. So, inherently, there are already two difficult choices that have to be made. But for the Red Sox, there are guys coming back from injuries as well, which will add more to the roster gymnastics to come. With that being said, here are four guys at risk of missing the postseason roster.

Greg Weissert — Relief Pitcher

Sep 13, 2026; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Greg Weissert (57) delivers a pitch during the eighth inning against the Kansas City Royals at Fenway Park. Mandatory Credit: Paul Rutherford-Imagn Images | IMAGN IMAGES via Reuters Connect

Weissert hasn't had his best season. He hasn't been bad, by any means. He has a 3.45 ERA in 61 appearances. But the bullpen is about to get tricky. Tyron Guerrero is about to be activated, which will lead to a change in the bullpen, with Raymond Burgos being the most likely to get the boot. Between now and the start of the playoffs, both Garrett Crochet and Tanner Houck could end up being options for the Red Sox as well.

Boston's bullpen is loaded already. When — if — it gets Crochet and Houck back, that's going to make for tough decisions in general. Do you send down Alec Gamboa with his 1.21 ERA in 19 outings? Do you send down Wyatt Olds with a 1.23 ERA in 12 appearances? Or do you send down Weissert? Two will be sent down if Crochet and Houck do return.

Connor Wong — Catcher

Aug 26, 2026; Miami, Florida, USA; Boston Red Sox catcher Connor Wong (12) returns to the dugout against the Miami Marlins after the eighth inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | IMAGN IMAGES via Reuters Connect

Like Weissert, this isn't a sign of a bad season. Wong has been better this year than he was last year. But, again, roster gymnastics are coming. Adley Rutschman is the main guy in Boston. After him, do you carry Wong on the roster as well as Mickey Gasper? Arguably, the best way to maximize the roster would be to carry Gasper as the emergency backup catcher and use Wong's roster spot elsewhere.

Andruw Monasterio — Infielder

Sep 15, 2026; Arlington, Texas, USA; Boston Red Sox shortstop Andruw Monasterio (32) reacts after striking out during the eighth inning against the Texas Rangers at Globe Life Field. Mandatory Credit: Kevin Jairaj-Imagn Images | IMAGN IMAGES via Reuters Connect

Monasterio is another guy who has played a solid role for Boston this season. But a roster crunch is coming and there are a few different guys who can do what he can. He plays all over the infield and Boston have a few guys who can do that. Plus, Monasterio hasn't been red-hot at the plate.

Jarren Duran — Outfielder

Sep 9, 2026; Boston, Massachusetts, USA; Boston Red Sox left fielder Jarren Duran (16) runs off the field during the sixth inning against the Los Angeles Angels at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | IMAGN IMAGES via Reuters Connect

It would be a bit of a surprise to see Duran not on the playoff roster, but it's something that has to at least be thought about here. Ceddanne Rafaela should be back in the coming days. That likely will lead to Nate Eaton being optioned. Then, the Red Sox's four outfielders are Rafaela, Duran, Roman Anthony and Wilyer Abreu. On top of them, Boston has Jahmai Jones as a lefty specialist. It would be a surprise if he's not on the playoff roster because of that.

On one hand, the Red Sox could roll with a lineup with Duran in left field, Rafaela in center field, Abreu in right field and Anthony as the designated hitter. Or, they could put Anthony in left field and Gasper or Jones as the designated hitter. It depends on how Boston views its best lineup. One guy who has been talked about a lot recently is speedy outfielder Braiden Ward, who has 60 stolen bases down in Triple-A.

If Duran isn't someone Boston has in the lineup each night in a playoff series, then arguably the conversation turns to pinch running. Duran is a speedster himself. Do you have him, or someone like Ward? Arguably, Duran should be on the roster. But he has struggled offensively this season, so it will at least be a conversation.

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