Red Sox World Series Champ Calls For Boston To Take ‘Aggressive’ Offseason Approach

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.

Outside of signing Trevor Story to a massive contract in 2022, the Boston Red Sox have followed a similar script when it comes to their recent offseason approach.

Whether it was Chaim Bloom or current Red Sox chief baseball officer Craig Breslow, Boston’s front office kept one eye on the future while electing to make more minor moves on the free agent and trade markets, acquiring veteran players on low-term, low-risk deals.

Will Middlebrooks, who won a World Series with the Red Sox in 2013 and serves as an analyst for NESN, wants to see things change this offseason.

Middlebrooks could get his wish with the Red Sox coming off a third straight disappointing season in which they finished third in the American League East with an 81-81 record. They haven’t played postseason baseball since 2021, either. Middlebrooks feels the Red Sox have several pieces in place and now is the time for them to add to that mix to get them back to contender status.

“This is the offseason where you’re aggressive,” Middlebrooks told NESN.com. “I think it’s time to start worrying about the now more than the future. And Craig Breslow’s made some comments to TC (Tom Caron) on ‘310 To Left’ recently about how it’s time to start paying more attention to the now. He made a really good point of you can’t keep asking this fan base to sit back and wait for the future to get here for you to go out and win the division.

“I think the positional player talent is here. There’s a lot of young talent. I think the full core is just about here with a couple guys that finished in Triple-A that are going to contribute in 2025. I think it’s time they build around that.”

Middlebrooks knows exactly where he would start on his offseason to-do list if he was in Breslow’s shoes. Middlebrooks wants the Red Sox to go out and obtain an ace to bolster the starting rotation.

There will be several strong arms available in free agency — Corbin Burnes, Max Fried and Jack Flaherty among others — but Middlebrooks would love to see the Red Sox pursue a trade for Chicago White Sox standout lefty Garrett Crochet. The 25-year-old All-Star, who posted a 3.58 ERA and a 1.068 WHIP while striking out 209 batters in 146 innings, was involved in trade rumors at this year’s trade deadline and it’s possible the lowly White Sox might look to deal him in the offseason.

Crochet at the top of the Red Sox rotation, which already has talented arms in Tanner Houck and Brayan Bello along with a solid back-end option in Kutter Crawford, would be a significant piece and get Boston, at least on paper, closer to playing October baseball again.

“I think something we’ve seen over the last few years is that they just kind of fall off a cliff. August, September, they don’t play good baseball, which playoff teams should never be able to play terrible baseball the last two months and get in,” Middlebrooks said. “So, you got to find a way to somehow stretch out your talent. Get guys to get to the finish line. And I think a lot of that is, you got to add an ace. There’s no way around it anymore.”