The White Sox are turning October into a full-on show, and the Red Sox have front-row seats to the whole thing.
Chicago has become one of the most entertaining teams in the 2026 season, and that hasn’t changed once the playoffs started. The wizard hats, magic wands and all that power-of-friendship energy carried the White Sox from 60 wins to 84 in a single year, and the party has kept rolling. Even the drunken Munetaka Murakami celebrations have become part of the postseason soundtrack, and there’s no sign the White Sox are slowing down now.
They’ve already swept the Houston Astros in the Wild Card series and jumped out to a 2-0 lead over the Cleveland Guardians in the ALDS. One more win, and Chicago finishes off the upset.
For Red Sox fans, the uncomfortable part is seeing so many familiar names driving it all. Murakami is the headliner, but Chase Meidroth, Kyle Teel and Braden Montgomery have been right in the middle of the action too.
Against Houston, Meidroth and Montgomery got Chicago going early in Game 1. In Game 2, Teel drove in the first run and later scored on an Andrew Benintendi single - yes, that Andrew Benintendi, another former Red Sox and 2018 World Series champion - and Meidroth added a home run.
Teel kept it going with another run in Game 1 against Cleveland. Then in Game 2, Montgomery ripped an RBI double to put the White Sox ahead by one, and Meidroth followed with an RBI single in the next at-bat to tack on another.
Meidroth, Montgomery and Teel were all included in the White Sox return in the 2024 Garrett Crochet trade. Each of them spent time in Boston’s farm system before reaching the majors months after the deal, though Montgomery’s stay was only a few months.
The trade has worked out for the Red Sox, even with Crochet missing almost all of his second season, and Boston has no reason to regret it. Still, watching those former prospects shine in October for another club after the Red Sox’s own playoff exit is a bitter pill.
Meidroth’s rise may sting the most. Boston has spent years trying to lock down a reliable second baseman, and he looked like the answer in Chicago.
He hit .276/.350/.415 with 31 doubles and 16 home runs across 154 games, and his 4.5 fWAR made him the best second baseman in the AL. Red Sox Chief Baseball Officer Craig Breslow has said he hopes Curtis Mead will be Boston’s starting second baseman next season, and Mead was in the middle of a breakout year before getting hurt shortly before the trade deadline.
But Meidroth delivered a full season of production, and he’s carrying that form into October with six hits and five RBI in four games.
Boston may not regret the Crochet trade, especially after extending him to keep him in town for years. But it still hurts to watch so many former Red Sox prospects thrive in the postseason with another team, especially after the way Boston’s own run ended. On the bright side, the White Sox have at least given Red Sox fans a clear AL team to pull for in this playoff race.
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