The Boston Red Sox certainly are at a crossroads right now.

Boston has a much-needed day off on Monday, but currently finds itself in last place in the American League East at 25-33. If that wasn’t bad enough, the Red Sox are currently the worst home team in baseball. Boston is 9-19 at Fenway Park. There isn’t another team in baseball with fewer than 11 wins at home. While the Red Sox have a day off on Monday, they are going to begin a tricky series on Tuesday night against the Baltimore Orioles at home. The Red Sox’s next nine games are against American League East foes and six of them are at home.

This very well could be the stretch that makes or breaks the 2026 Red Sox. If the Red Sox lose these series, there is a real chance that the club will find itself in too big a hole by the middle of June to come out of. Hopefully, that doesn’t happen. But that’s why the Red Sox are at a crossroads.

The Red Sox Boss Isn’t Concerned About Himself

The season didn’t begin as expected and that led to former manager Alex Cora and a handful of coaches being fired. What’s next? If Boston doesn’t turn its season around, all eyes are going to turn to chief baseball officer Craig Breslow. Boston has proven over the years that it’s not willing to sit around and wait for decision makers to get it right. Dave Dombrowski was let go in 2019, a year after the the Red Sox won the World Series in 2018. Chaim Bloom came in to replace him and was given an impossible task of breaking up the 2018 World Series core and rebuilding. Still, the Red Sox let him go in 2023.

Breslow came in afterward with a much-improved farm system than when Bloom came to town, but things haven’t been perfect. Boston was a .500 team in 2024. The Red Sox took a step forward with 89 wins in 2025, but there were also some pretty public missteps, like everything that happened with Rafael Devers. Boston let Alex Bregman walk after the 2026 season, and the campaign has been a disaster from the jump. While this is the case, Breslow made it clear to Tim Healey of The Boston Globe that he’s not concerned about the job security right now.

“When you talk about analytics — I can be very practical,” Breslow said. “Which is to say, OK, is thinking about job security going to make me better at my job or worse at my job?” I don’t know how it would make me better. So I focus on all the things that are part of this job and ultimately get us where we want to go.”

He made a similar point before the season began.

While he may not be concerned about his job security, he’s going to be under a microscope if the club doesn’t turn things around. That’s for sure.