Will Middlebrooks Issues Caution About Star Free Agent Linked To Red Sox

Sox Talk with Will Middlebrooks is a recurring content series on NESN.com. Middlebrooks, a former Red Sox player, and current NESN analyst gives his insight and opinion on pertinent Red Sox storylines throughout the season. You can read the latest stories from the series here.

Red Sox chief baseball officer Craig Breslow was adamant about adding a right-handed bat to balance out Boston’s left-heavy lineup for next season.

And the Red Sox were linked to one before this past campaign even came to a close. He has a solid glove, too, which is something else Breslow is in search of this offseason to improve Boston’s defense.

The Athletic’s Ken Rosenthal in mid-September floated longtime Astros third baseman Alex Bregman, who spent all nine of his MLB seasons with Houston, as a possible free agent target for the Red Sox. Bregman does check some boxes for Breslow, but former Red Sox third baseman and NESN analyst Will Middlebrooks believes Boston should tread carefully in a potential pursuit of the two-time All-Star.

“The only thing is Bregman looking for $200 million?” Middlebrooks told NESN.com. “He’s (about to be) 31 years old, how are you going to pay this guy? It’s not my money. I get that. It’s not Craig Breslow’s money. It’s beyond that. But do you really want to sign one of those contracts where you’re eating the last three years of it? The year 37, 38, 39 of how old he is in that contract, what are you really getting from him? Is he going to be a good third baseman at that point when you have nowhere else to put him? No.

“Depending on the deal, I would love Bregman. I wouldn’t want to overpay and overextend on years when you’re going to be eating the back end of that.”

It’s unclear how much of a shot teams outside the Astros will have at signing Bregman. If you ask Jose Altuve, there’s no chance Bregman leaves Houston.

Bregman is in line to get a sizable contract, one that might be too pricey for the Red Sox. The Athletic’s Jim Bowden predicted Bregman could get a deal in the range of seven years and $185.5 million.

The extended years and money obviously is where Middlebrooks throws up the caution flag for the aging star. Bregman’s offensive production ever since a sensational 2019 season, in which he batted a career-high .296 with 41 home runs and 112 RBIs to go along with a league-leading 119 walks, has steadily declined.

He hasn’t hit over 30 homers in a season since then and is batting .262 over the last four seasons. He did drive in 98 runs in 2023 but saw his RBI total take a hit this past season when he only collected 75.

Signing Bregman would more than likely mean a position change for Rafael Devers, either to first base or designated hitter, with Bregman providing better defense at the hot corner.

Bregman also has a deep connection to Red Sox manager Alex Cora. Bregman won his first of two World Series titles when Cora was on Houston’s coaching staff. Bregman’s winning pedigree would fit in nicely to help guide a young Red Sox team, but Boston undoubtedly would have to dip into its pockets to make that happen.

“I would love him in the clubhouse. I would love him with that young group of guys. I would love him pushing everyone and making everyone better around him,” Middlebrooks said. “I just don’t know if the price tag matches with the years. I would go higher AAV for a shorter contract. But you don’t need to be eating $20 (million) a year on the back end of that or more.”