Why Red Sox Didn't Trade for Brendan Donovan, Explained

Craig Breslow isn't one to give into fan pressure...

Sep 19, 2025; St. Louis, Missouri, USA; St. Louis Cardinals second baseman Brendan Donovan (33) celebrate with first base coach Packy Elkins (86)after hitting a single against the Milwaukee Brewers during the fifth inning at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images | Jeff Curry-Imagn Images

They did it twice before, so why not a third time?

After acquiring All-Stars Sonny Gray and Willson Contreras from the St. Louis Cardinals earlier this offseason, the Boston Red Sox remained in the mix for second baseman Brendan Donovan, seemingly right up until the Seattle Mariners reportedly agreed to trade for him on Monday, pending medicals.

To boil things down to their simplest terms, the Red Sox and Donovan just weren't a great fit. He would have made them better in the short term, no doubt, but there were some fairly obvious indicators all along that he wasn't the target who made the most sense to solve the infield.

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Red Sox, Cardinals didn't line up

Sep 13, 2025; Milwaukee, Wisconsin, USA; St. Louis Cardinals second baseman Brendan Donovan (33) hits a solo home run against the Milwaukee Brewers in the third inning at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | Benny Sieu-Imagn Images

Donovan fit the Red Sox's obvious need for a second or third baseman, and as a slightly above average defender, he would have fit Craig Breslow's stated desire to prioritize run prevention, which will matter more to the Red Sox this year with Ranger Suárez near the top of the rotation.

However, Donovan bats left-handed, and Boston's lineup already skews far too lefty-heavy. You can get away with another lefty addition if the player in question has even platoon splits, but Donovan is much, much better against right-handed pitchers than lefties.

Ari Alexander of WHDH-TV reiterated his own reporting on Monday that the Red Sox were lower on Donovan than other prospective targets, largely because of his left-handed bat. Boston "wanted more lineup balance," per Alexander.

Donovan also only hit 10 home runs last season and has a career high of 15. Boston's first stated objective this offseason, before the goalposts seemingly started to move sometime around mid-January, was to add home run power.

Not many Red Sox fans would have been mad about trading for Donovan, and in fact, some probably hoped it would happen. But whatever package it would have taken, in the context of the five pitchers the Red Sox had already sent to St. Louis in the other two trades, clearly wasn't something Breslow was comfortable paying.

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