Former Red Sox Top Prospect's White Sox Debut Stings for Boston Fans

Bosotn Red Sox fans can't catch a break right now, to say the least.

The 2025 season was a good one for the club overall, but the last few years have been difficult in general. Boston went 78-84 and finished in last place in the American League East in both 2022 and 2023. In 2024, the Red Sox were a .500 team. In 2025, the Red Sox finally turned things around, although there were bumps along the way with Rafael Devers being traded away.

But the 2026 season has been a significant step backwards so far. The Red Sox have been stacking up losses and now are 11 games below .500 at 27-38. On top of the bad season overall in the standings, Boston is currently missing Garrett Crochet and Roman Anthony right now. Also, another player who has been expected to play a big role is down in Triple-A in Brayan Bello. It's been a trying season full of offensive struggles and plenty of negative chatter, specifically about letting Alex Bregman walk this past offseason and not replacing him with another big bat on top of adding Willson Contreras.

It Hasn't Been Boston's Year

Apr 29, 2021; Arlington, Texas, USA; A view of the Boston Red Sox logo and a field bag during batting practice before the game between the Texas Rangers and the Boston Red Sox at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images | Jerome Miron-Imagn Images

If all of that wasn't bad enough for Red Sox fans, a few former members of the organization are thriving elsewhere. The Chicago White Sox are full of former Red Sox prospects thanks to the Crochet deal. Right now, the big lefty is on the shelf. In Chicago, Chase Meidroth has thrived this season and is slashing .274/.344/.390 in 64 games played. On Tuesday, former Red Sox first-round pick Braden Montgomery made his big league debut and smashed a walk-off homer in his first game in the majors.

BRADEN MONTGOMERY HITS A WALK-OFF HOMER IN HIS MAJOR LEAGUE DEBUT! pic.twitter.com/ifxPs2t57F
— MLB (@MLB) June 10, 2026

Montgomery is just the latest former member of the Red Sox organization to make a big impact this season. It has been talked about all season to this point that former Red Sox hurler Kyle Harrison is thriving over with the Milwaukee Brewers. He has a 2.72 ERA in 12 starts so far this season. Former Red Sox fan favorite and World Series champion Chris Sale is still thriving after being traded to the Atlanta Braves for Vaughn Grissom. Sale has a 2.23 ERA in 12 starts so far this season in his third campaign in Atlanta. He had a 2.38 ERA in his first season in Atlanta in 2024 and a 2.58 ERA last year.

Even Grissom is thriving elsewhere. He was traded to the Los Angeles Angels and is slashing .246/.325/.410 with a .735 OPS, four homers and 27 RBIs in 40 games played. All in all, it hasn't been the Red Sox's season so far and there are guys all across the league rubbing salt in the wounds of Boston fans.

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