The Boston Red Sox have been agents of chaos for the last calendar year. Will that trend continue into this offseason?

It’s clear that the Red Sox are taking an aggressive approach to their current championship window, as evidenced by moves ranging from blockbuster trades to acquire Garrett Crochet and dump Rafael Devers to cutting two-time All-Star Walker Buehler with a month remaining in the regular season.

Now, with the offseason approaching, the Red Sox have to be considered a threat to sign some of the biggest names in free agency. That includes one of their own in Alex Bregman, but it could also include a slugger who used to be theirs, if only for a short window.

Kyle Schwarber has become a huge fan favorite for the Philadelphia Phillies after signing a four-year contract at the end of his Red Sox tenure in 2021. But although he only played 41 regular-season games for the Red Sox, he was beloved in Boston too, and whispers have circulated that the Red Sox might be interested in a reunion as well.

On Thursday, FanSided insider Robert Murray predicted that Schwarber would ultimately re-sign with the Phillies, but identified the Red Sox as the biggest threat to poach the 50-homer All-Star away from his squad of the last four seasons.

“My guess is that the Phillies pay up and keep Schwarber. He’s too valuable, too loved inside that organization, and John Middleton and Dave Dombrowski have a history of paying key players like Schwarber,” wrote Murray.

“If he does leave … give me the Boston Red Sox. He’s loved in Boston, and seeing him back in Fenway on a three- or four-year contract would be super fun.”

Spotrac currently projects Schwarber for a four-year, $100.5 million contract, which could prove to be a low-end estimate if two big-market teams like Boston and Philadelphia wind up in a bidding war.

Being the runner-up in a free agency chase doesn’t do anything for a club, as the Red Sox have proven by continually showing interest, whether genuine or not, in the top free agents of the past half-decade.

There’s also Alex Bregman to consider. If the Red Sox are going after Schwarber, does that mean their odds at a Bregman reunion are lessened, or could Boston be preparing for a major payroll increase that includes both stars?

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