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Greg Weissert, Red Sox bullpen implosion vs. Rays fueled a late-night roster move

May 3, 2026; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Greg Weissert (57) pitches against the Houston Astros during the fifth inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images
May 3, 2026; Boston, Massachusetts, USA; Boston Red Sox relief pitcher Greg Weissert (57) pitches against the Houston Astros during the fifth inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

The Boston Red Sox on May 8 entered their four-game series against the Tampa Bay Rays fresh off their first series sweep of the season. Aggressive, early offense and a solid performance from top pitching prospect Jake Bennett helped the Sox rush out to a 3-3 tie with one of the best teams in the American League.

But once Bennett left the game, the score tilted in the Rays' favor. Bennett let up a sixth-inning single before punching out Jonathan Aranda before Greg Weissert entered the game. The righty allowed a single, a walk, then another two-run single to put Boston two runs behind. it's the fourth lead Weissert has blown over his 17 appearances this season.

"It's no secret. I'm pitching like s--t," Weissert told reporters after the game, owning up to his recent struggles. He's posted a 5.52 ERA with 18 strikeouts and five walks over 14.2 innings this season.

Some disgruntled fans across social media have called for the Red Sox to designate Weissert for assignment, but there's no reason for them to take such a drastic action. Not only has Weissert previously been quite successful in a Red Sox uniform (2.97 ERA over 130.1 innings from 2024-25), he still has a minor league option on his contract, meaning the Red Sox can send him to Triple-A without having to put him through waivers.

Red Sox righties Greg Weissert and Ryan Watson's struggles continue out of the bullpen, Boston calls up Jack Anderson

The Red Sox don't have the same luxury with another struggling reliever, Ryan Watson. He entered the game in the seventh inning after Tyler Samaniego. After he collected one out in the eighth frame, he allowed a single to Ben Williamson and a triple to Chandler Simpson, officially putting the game out of reach for Boston.

Watson has logged a 6.46 ERA over 23.2 innings with the Red Sox. He hasn't entered too many games with a lead, but his numbers aren't impressive, regardless. If Boston ever hopes to move on from him, he would have to be offered back to the San Francisco Giants, his team from last season, as he was a Rule 5 Draft pick. Letting him go would cost the Red Sox one of their most used arms, regardless of how rough he's looked.

After Weissert and Watson's unfortunate performances in the series opener, the Red Sox have summoned righty reliever Jack Anderson and sent Bennett back to Triple-A. Anderson has allowed three runs on eight hits with six strikeouts and two walks over eight innings in the big leagues this year.

Watson and Weissert will be unavailable after their outings on May 7 so Boston had to call up another righty reliever to be ready to go in the second game of the Rays series. Connelly Early will get the start against the Sox's division rivals this evening.

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