As the Boston Red Sox grappled with their June 9 series loss to the Tampa Bay Rays and their complete offensive incompetence, a former Red Sox player saved the day for his current team.
Former top Red Sox prospect Braden Montgomery made his major league debut for the Chicago White Sox and instantly joined the ever-growing group of one-time Red Sox players who already have incredible accomplishments under their belt for 2026. Montgomery logged two hits and three RBI in his Chicago debut.
One of the hits was a walk-off home run. The White Sox had Andrew Benintendi on third base in the 10th inning against the Atlanta Braves, the best team in baseball, and Montgomery delivered in the loudest possible way to cap off an incredible debut.
Former Red Sox players are having rebound seasons across MLB, from Kyle Harrison to Dustin May to Los Angeles Dodgers prospect James Tibbs III. Top pitching prospect David Sandlin on May 27 made an incredible one-hit, one-run debut for Chicago. Now, Red Sox fans might have to watch Montgomery thrive with the White Sox, as well.
Braden Montgomery joins growing group of former Red Sox with incredible achievements in 2026
In one night, Braden Montgomery made his MLB debut and collected his:
— MLB (@MLB) June 10, 2026
- first hit
- first RBI
- first home run
- first walk-off
- first walk-off home run pic.twitter.com/22TxG9k1v0
Boston traded Montgomery to Chicago as part of the 2024 Garrett Crochet trade, alongside Kyle Teel, Chase Meidroth and Wikelman Gonzalez. Teel and Gonzalez are injured at the time of Montgomery's debut, but they've played well with the White Sox when healthy. Meidroth is still a consistent hitter (.274/.344/.390 over 64 games) with above-league-average defensive range.
Of course, as the Red Sox continue floundering while Crochet approaches his seventh week on the injured list, Boston fans will be dramatic. Social media discourse on whether the Red Sox won or lost the Crochet trade has begun following Montgomery's heroism. The answer is: of course the Red Sox haven't lost the trade.
Even if every player the Red Sox gave up in the trade becomes a successful big leaguer, it's a trade they should make again in a heartbeat. Crochet has already shown he can be one of the best pitchers in the league and he would be irreplaceable on any roster. The Red Sox extended him for six years shortly after his arrival, as they should've. One IL stint with Boston doesn't change his career outlook — Crochet is still an ace by every measure.
Still, watching former Red Sox players at their best while the current Red Sox can't get out of their own way is demoralizing, especially when the expectations for this year's team were so high. Montgomery is expected to be a great player, which Boston knew when it traded him away, a risk teams have to take to land top-tier talent like Crochet. Talented outfielders come around much more often than arms like Crochet.
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