"I wish they would spend more" - Red Sox legend Jonathan Papelbon questions owner John Henry's strategy amid disappointing offseason

The Boston Red Sox are having a tough offseason. They were in talks with Shota Imanaga but lost out to the Chicago Cubs. They were also interested in Yoshinobu Yamamoto, and nothing came of that, either.

The Red Sox have not made any significant acquisitions this offseason, apart from the arrivals of Max Castillo, Vaughn Grissom and Lucas Giolito. While Grissom and Giolito may prove to be valuable, their failed pursuit of top free agents has disappointed fans and experts alike, including Red Sox legend Jonathan Papelbon.

On a recent episode of the "Foul Territory" podcast, Papelbon expressed his dissatisfaction with Boston's offseason strategy. He also expressed doubts about owner John Henry's plans to improve the Red Sox for 2024.

“I think that John Henry and his ownership group ... they have the soccer team, the NASCAR team, the baseball teams, and I think a few other teams, but they all had their own ways,” Papelbon said.

“He gives each one of those teams 'X' amount of dollars to spend, and I don't know how much that is. ... I wish they would spend more, but I don't know where they're at.”

John Henry is the founder and principal owner of Fenway Sports Group, which controls three major sports teams: the Boston Red Sox, Liverpool FC, and the Pittsburgh Penguins. In addition, he serves as the director of NASCAR's RFK Racing.

Under Henry's ownership, the Red Sox have won four World Series pennants and five AL East titles and made 11 postseason appearances. However, the Red Sox had a below-par season in 2023, finishing at the bottom of their division with only 78 wins.

Boston Red Sox in the offseason

In 2023, several Red Sox players, such as Adam Duvall, Adalberto Mondesi, James Paxton and Corey Kluber entered free agency.

However, this offseason, they have only signed two free agents: Cooper Criswell and Lucas Giolito. It has been two years since the team made it to the postseason.

If their fortunes are to turn, the Red Sox desperately need to address some gaping holes in their squad, and they need to do it soon.