The Boston Red Sox have to be well acquainted with the area code for St. Louis at this point in the offseason.
The Red Sox and St. Louis Cardinals have already made two hugely significant trades this winter. Boston nabbed starting pitcher Sonny Gray from St. Louis just before Thanksgiving, then acquired first baseman Willson Contreras just before Christmas.
There’s no major holiday approaching at the moment, but the possibility of the Red Sox and Cardinals teaming up for a third and final big-time trade this winter remains very much alive.
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Red Sox still in play for Brendan Donovan, says insider 
Apr 6, 2025; Boston, Massachusetts, USA; Boston Red Sox shortstop Trevor Story (10) leaps out of the way as St. Louis Cardinals infield Brendan Donovan (33) continues to slide into second base during the ninth inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images
The Red Sox have quite an obvious need for another infielder at the moment, and it seems that based on everything they’re either saying or signaling through the media, they’d prefer that infielder be a second baseman with a good glove.
In a Monday column, insider Ian Browne of MLB.com signaled that he still believed the Red Sox could trade for Brendan Donovan, the Cardinals’ All-Star second baseman who has two years left on his contract before free agency.
“Though a right-handed bat has been the preferred bat all along, don’t rule out yet another trade with the Cardinals for Brendan Donovan, who is known for his strong defense,” Browne wrote. “Run prevention is the buzzword for the 2026 Sox. Donovan would certainly help in that regard. He isn’t eligible for free agency until the 2028 season.”
Donovan, 29, is a well-rounded player who nonetheless makes an imperfect fit for this Red Sox roster. He’s a left-handed bat, something they already have in droves, and he hit just 10 home runs last season, with a career-high of 14 in 2024.
There would surely be Red Sox fans apprehensive about trading more talent to ex-Boston exec Chaim Bloom and the Cardinals. Donovan is a gamer, but he’s also not as dynamic as a future star in the rotation could be.
But the other uncomfortable reality is that the Red Sox would have a better chance to win in the new year with Donovan than they would be if they stood pat.
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