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Former Boston Red Sox Prospects Help Propel White Sox Into Divisional Round
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- Former Boston Red Sox Prospects Help Propel White Sox Into Divisional Round
RedSoxRoundtable's Zach Coe discusses the success of a trio of former Boston Red Sox prospects, now members of the Chicago White Sox, in the Wild Card round. Be sure to join our FREE community over on RedSoxRoundtable.com!
While the Boston Red Sox and New York Yankees were just getting underway in New York's blowout Game 2 win of the wild card series on Wednesday, the celebration was on in the visitors clubhouse at Houston's Daikin Park, where the Chicago White Sox swept the Houston Astros in their series.
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The win over Houston marks Chicago's first playoff series victory since their 2005 World Series clinching victory over those same Astros, and this time, they were powered by four former Boston Red Sox prospects: Chase Meidroth, Kyle Teel, David Sandlin and Braden Montgomery.
Meidroth, Teel, and Montgomery were all dealt to Chicago ahead of the 2025 season in the blockbuster trade that sent ace Garrett Crochet to Boston . Both Teel and Meidroth made their big-league debuts in 2025 and became major pieces in Chicago's rebuild, while Montgomery arrived in June of this season.
After initially being seen as more of a throw-in in the Crochet deal, Meidroth has become an incredibly productive big leaguer in Chicago, hitting .276/.350/.415/.765 with 16 home runs in 154 games, and providing strong defense at second base. The 25-year-old thrived in his first taste of postseason action, going 4-for-7 with a home run and four RBI in Chicago's sweep over Houston.
Sep 30, 2026; Houston, Texas, USA; Chicago White Sox second baseman Chase Meidroth (10) rounds the bases after hitting a three-run home run against the Houston Astros in the sixth inning during game two of the Wildcard round for the 2026 MLB Playoffs at Daikin Park. Troy Taormina-Imagn Images
After his major league debut on June 9, Montgomery struggled in his first big-league action, hitting .226/.312/.350/.662 with six home runs in 93 games. Despite those struggles, the 23-year-old went 2-for-8 with a pair of singles in this series.
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Once thought of as the catcher of the future in Boston and an original member of the 'Big Three' prospects alongside Roman Anthony and Marcelo Mayer, Teel, as well as Montgomery, were the headliners of the package heading back to Chicago for Crochet.
The 24-year-old made his major league debut on June 6, 2025, and quickly established himself at the plate, hitting .273/.375/.411/.786 in 73 games. However, he struggled in an injury shortened 2026 season, hitting just .210/.336/.361/.697 in 32 games. Teel went 3-for-10 in the White Sox sweep in Houston, including an RBI single.
Of course, Boston doesn't regret the deal for Crochet, even though he missed most of the 2026 season with a left shoulder injury. The 27-year-old left-hander is expected to remain one of the best starting pitchers in the game and is under contract with Boston through at least the 2031 season at a fairly affordable $28.3 million average annual value.
Sep 30, 2026; Houston, Texas, USA; Chicago White Sox catcher Kyle Teel (8) runs the bases after hitting an RBI single against the Houston Astros in the first inning during game two of the Wildcard round for the 2026 MLB Playoffs at Daikin Park. Troy Taormina-Imagn Images
However, they might regret at least two of the pieces it took to acquire Crochet's services. Initial discussions around Crochet centered on Mayer, who was dealt to San Francisco in exchange for reliever Erik Miller ahead of the 2026 trade deadline after underperforming in Boston. Could including Mayer in the package have saved the team from including Teel in the deal, and thus saved Boston Chief Baseball Officer Craig Breslow from emptying the farm system to acquire Adley Rutschman ?
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What about Meidroth? At the time of the trade, Mayer and fellow top prospect Kristian Campbell were expected to handle the middle infield in Boston for the foreseeable future, making Meidroth, a fringe top-10 organizational prospect, more expendable. However, Campbell struggled mightily defensively at second base, prompting a move to the outfield and leaving a massive hole at second base. In 2026, Red Sox second basemen posted a wRC+ of 87, tied for the eighth-lowest mark in the sport, while Meidroth posted a 118 wRC+, the fifth-best mark among all qualified second basemen. Was there any wiggle room on including a different, similarly rated player in the deal instead of Meidroth?
Ultimately, nothing can change the package sent to Chicago, but the trio's success will be something to watch as the White Sox continue their pursuit of a World Series title, while the Red Sox watch from home.
And as for Sandlin, he threw 1.1 scoreless innings in the wild card round after going 3-2 with a 5.58 ERA in eight regular season appearances. The Red Sox traded him to the White Sox last offseason along with reliever Jordan Hicks, who struggled in his limited time in Boston. Hicks was lights out for Chicago's bullpen in this series as well.
