Many reporters and fans have expected an active Winter Meetings from the Boston Red Sox — not only have they kicked the offseason off with some of the biggest, out-of-nowhere trades so far, but their needs are very clear after their early postseason elimination.
Red Sox chief baseball officer Craig Breslow has also exceeded expectations at the Winter Meetings before. In 2024, he pulled off the trade of the offseason by swapping four top prospects for Chicago White Sox ace, Garrett Crochet.
The latest Red Sox rumors suggest he may hope to undo part of that trade. Boston has expressed interest in trading for Kyle Teel, the former Red Sox top catching prospect involved in the Crochet deal, according to Sean McAdam and Chris Cotillo of MassLive.
The White Sox traded for Teel knowing they already had a top catching prospect in Edgar Quero, who, like Teel, made his MLB debut last year. Chicago is reportedly entertaining the idea of trading one of its young backstops, but there is no deal close to its conclusion now.
Red Sox reportedly interested in trading for their former top prospect Kyle Teel from he White Sox
McAdam and Cotillo report that the White Sox are seen as more willing to trade Quero than Teel, and they did not mention whether Boston would be interested in acquiring Quero if Teel is off the table. If it takes this pursuit for Teel seriously, it would come at quite a cost, as there's no way the White Sox would so easily allow it to undo part of the Crochet trade that has already worked out so well.
A few weeks before the Winter Meetings, reports emerged that Boston has expressed interest in signing veteran catcher J.T. Realmuto. The Red Sox don't exactly need to upgrade their catching tandem, although they're open to new additions — Carlos Narváez emerged as a defensive savant and capable No. 1 last season, and Connor Wong is a serviceable backup in a normal season when he isn't playing through a hand injury.
The Red Sox now have a glut of starting pitching depth they could trade from in attempt to reunite with Teel, along with an outfield logjam they need to clear this winter. But if the White Sox aren't inclined to trade him, there may be nothing the Red Sox can do to get their former top prospect back. If they did get him back, it'd be a rare, flip-flop of a deal that we may never see again.