Ex-Yankees $86 Million Superstar Could Be Prime Target For Red Sox

The Boston Red Sox have a few holes to address on the roster this winter.

If the Red Sox want to contend in 2025, they will need to add one frontline starting pitcher, one right-handed bat for the middle of the lineup, and at least one or two dependable starters. This is just the beginning of what the club could use, and it's really unclear how the offseason will shake out.

The bullpen really needs to be addressed this winter after a rough second half of the season. Boston's struggling bullpen arguably is the biggest reason why the team is on the outside looking in on the American League Wild Card race right now.

Boston should be in the market for at least two dependable hurlers, and at least one should be left-handed. Because of this, former New York Yankees and current Pittsburgh Pirates star Aroldis Chapman should be in the conversation for Boston in free agency.

The Red Sox clearly are familiar with him after facing off against him as a member of the Yankees for years. He may not be as dominant as he once was, but he still boasts one of the best fastballs in all of baseball and has a 3.97 ERA this season across 65 outings for Pittsburgh. At one point, he was one of the best relievers in baseball and signed a mammoth $86 million deal with the Yankees, but he is much more affordable now.

The Red Sox have struggled to find left-handed relievers, but Chapman could fix that. He is 36 years old now, but he clearly still has plenty left in the tank. He has had continued success as a lefty reliever even as his role has shifted from being a closer to a set-up man. Boston doesn't need him to come in and close games, but it does need a dependable lefty in the bullpen, and Chapman could be that guy.