The Boston Red Sox have completely changed their fortunes this season. A month ago, they were 11 games under .500 and appeared to be surefire sellers with the trade deadline coming up. But things suddenly changed, and now Boston is in the third American League wild card spot.
With that, they are now likely buyers, and they have clear needs to address. According to Buster Olney of ESPN, they have a clear need in mind.
“The Red Sox have been searching for a shortstop, in a market notably thin in shortstops,” Olney posted on X.
Ken Rosenthal and Will Sammon of The Athletic reported last week that Boston views Los Angeles Angels shortstop Zach Neto as a strong fit. But if that doesn’t pan out, there is somebody else Boston could take a look at: St. Louis Cardinals shortstop Masyn Winn.
Boston Red Sox Should Pursue Masyn Winn if Zach Neto Pursuit Fails
Neto may have a very high price tag, which could complicate things for the Red Sox, especially in a market with few shortstops even on the block. The Cardinals would likely have a high price for Winn too, but the two teams actually match up quite well.
The Cardinals are in need of young and controllable starting pitching prospects, and Boston has a strong pitching pipeline. Even 2011 World Series champion Lance Lynn believes that if the Cardinals can get that in a trade for Winn, they’ll have to at least consider because JJ Wetherholt could inherit the position.
“I make this move only if I think this. Do I think JJ can play a shortstop every day that I can get away with trading Masyn Winn for something that is really forward moving on maybe the pitching side, and I say, ‘Hey, maybe I can get a top three or a young one or two from a contending team?” Lynn said. “I think you have a serviceable shortstop that you just gave 100-plus million dollars to.”
The Red Sox need more offense, and Winn can provide that if given the chance to play for a contender. Boston has picked itself right up off the mat, while St. Louis is crashing back down to earth after a hot start to the 2026 season.
So, if Neto is too expensive, Winn could be a perfect plan B for the Red Sox, as he can provide elite defense at shortstop.
What Masyn Winn Would Bring to Boston Red Sox
Winn won a Gold Glove last season with St. Louis, so Boston would obviously have to put him at the shortstop position. Meanwhile, they could move Trevor Story to second base, Caleb Durbin back to third base and have a utility role carved out for the newly acquired Curtis Mead.
They would have to give up some pitching to make it work, but their offense would be much deeper as a result of this potential trade, and they would have an elite defender at shortstop.
The Red Sox have also done business with Chaim Bloom in recent months, so a trade is not out of the question.
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