Why Upcoming Stretch Is 'Make Or Break' For Scuffling Red Sox
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The Boston Red Sox were unable to capitalize on their most recent homestand, going 1-5 against the Minnesota Twins and Atlanta Braves and falling to 23-32.
Unfortunately, their schedule is about to get quite difficult heading into their final series of May against the Cleveland Guardians, who lead the AL Central and are 12-4 over their last 16 games.
After that, the Red Sox open June with three straight series against divisional opponents in the Baltimore Orioles, New York Yankees and Tampa Bay Rays, with the Yankees and Rays owning the two best records in the American League entering play on Friday. The rest of June features series against the Toronto Blue Jays, Seattle Mariners, Colorado Rockies, another series against the Yankees and the Washington Nationals.
With four divisional series coming up next month, Boston has a chance to make up some ground in the AL East, where it's currently in last place and 12 games out of first. It's a critical stretch for the Red Sox as they try to put their slow start behind them and build some momentum leading up to the All-Star Break.
Could the Red Sox hand the keys to another front office executive to handle the trade deadline?@ChrisCotillo explains why "it's such a tough decision to make." pic.twitter.com/Cn2sGvbB0E
— Monster Territory (@MTerritoryPod_) May 28, 2026
"The schedule is very difficult," MassLive's Chris Cotillo said during his appearance on Thursday's episode of the "Monster Territory" podcast. "Obviously the reinforcements are gonna help in the form of Anthony and Crochet in the next couple weeks, but these are kind of make-or-break weeks and make-or-break months in terms of the direction of the organization."
The next month will be a crucial test for Boston's roster as the front office evaluates which direction to go at the trade deadline. If the Red Sox hold their own and stay in the playoff race, the team will likely look to add at the trade deadline. If they continue to flounder and fall out of contention, however, selling becomes a more realistic possibility.
Time will tell if Boston is able to rise to the occasion. The Red Sox did around the same time last year, but it remains to be seen if they can do so again.
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