MLB Rumors: 3 teams who can’t miss on Jordan Montgomery in drying-up market

1. Boston Red Sox need to sign some big free agent this winter

The Boston Red Sox finished the 2023 season as the only team in the AL East to have a losing record. Not to mention, they finished in last place. The Red Sox faithful want to see the team in contention for the World Series. But so far this offseason, the team hasn't shown much to them that they are willing to build a winning roster.

Replacing Chaim Bloom is former pitcher Craig Breslow, who served as the assistant general manager for the Chicago Cubs. Thus far, the only significant signing from the Red Sox has been Lucas Giolito. Sure, it's a solid move, but it doesn't exactly move the needle. Not to mention the team traded away Alex Verdugo to the rival New York Yankees and replaced him with Tyler O'Neill of the St. Louis Cardinals. Oh, and dealt Chris Sale to the Atlanta Braves in exchange for infielder Vaughn Grissom.

Speaking of the Sale trade, the Red Sox now have a need for a left-handed pitcher in their rotation. Montgomery fits the bill perfectly. The Red Sox have seen Montgomery over the years during his time with the Yankees, but he has proven to be a top of the rotation arm since they traded him in 2022 for outfielder Harrison Bader.

Jon Heyman of the New York Post lists the Red Sox as one of the teams interested in Montgomery's services.

The Red Sox faithful are waiting for the big splash transaction of the offseason, and it has yet to happen. Montgomery would be a great get for Boston.