This offseason, Chaim Bloom will face his biggest test since assuming the role of Boston Red Sox chief baseball officer in 2019.
Xander Bogaerts' contract situation is priority No. 1. The star shortstop is set to opt-out of his Red Sox contract and become an unrestricted free agent for the first time in his career.
Tomase: Arbitration projections hint at Red Sox' offseason plans
Stay in the game with the latest updates on your beloved Boston sports teams! Sign up here for our All Access Daily newsletter.
Veteran designated hitter J.D. Martinez also will hit the open market along with right-hander Nathan Eovaldi and a handful of other key players. Rafael Devers is under contract with Boston through 2023, but Bloom should look to lock up his All-Star third baseman long-term to avoid a Bogaerts-like situation this time next year.
Failing to extend Bogaerts and losing him in free agency not only would affect the Red Sox on the field, but would also have a major impact on the clubhouse. The two-time World Series champion has quietly become a leader behind the scenes over the last few years.
Red Sox legend Pedro Martinez warns that letting Bogaerts walk, along with J.D. Martinez, would deter Devers from signing with Boston and cause a culture shift within the organization.
"If Xander opts out and leaves the team and J.D. [Martinez] leaves the team, I think [Rafael] Devers is most likely going to head the same way. Those guys are going to go. They're not going to have the essence of the franchise that we left," Martinez told Alex Speier of The Boston Globe.
Boston Red Sox
Find the latest Boston Red Sox news, highlights, analysis and more with NBC Sports Boston.
"The culture that we left is going to be lost. And we don't know when we're going to get it back and how we're going to get it back."
As Speier explains, Martinez is referring to the connection Bogaerts and Devers had with Red Sox greats David Ortiz and Dustin Pedroia, and the bond Ortiz and Pedroia were able to have with himself and Jason Varitek. If Bogaerts, Martinez, and Devers depart, that connection of the franchise's up-and-comers to its championship past will be lost.
The good news is Bloom said during his end-of-season press conference the front office will immediately prioritize working out a deal with Bogaerts. That, of course, is only step one in what looks to be a busy offseason for a Red Sox team looking to escape the cellar of the American League East in 2023.