Red Sox World Series Champion Opens Up About Not Going Into Coaching

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.

Boston Red Sox 2013 World Series champion Will Middlebrooks can look around baseball at all levels and see several of his former teammates in the coaching ranks.

Mike Napoli and Quintin Berry are both first base coaches with the Chicago Cubs and Milwaukee Brewers, respectively. David Ross managed the Cubs for four seasons before he was fired following the 2023 campaign. Jarrod Saltalamacchia is looking to work his way up the coaching ladder as he spent the last three summers as an assistant coach in the prestigious Cape Cod Baseball League.

Middlebrooks thought he could find a home in coaching, too, and seriously considered it once his playing career ended in 2019 after trying to mount a comeback from a severe leg injury, which included a broken fibula.

But Middlebrooks, who has served as a Red Sox analyst on NESN since 2022, made the tough decision to not jump into coaching despite opportunities in front of him.

“There were some offers from multiple teams to come on as like an assistant hitting coach or hitting coach of a minor league team,” Middlebrooks told NESN.com. “I had a lot of interest in that. And then I really sat down and thought about grinding out bus rides all summer. And at the time, I got hurt in spring training of 2018, rehabbed all year, tried to come back, but January of 2019 pulled the plugged and decided I couldn’t play anymore. But a couple months previous in October of ’18, my oldest daughter was born, our first kid. That changed the decision, too, not wanting to be gone for seven, eight months at a time from spring training through the end of the season and missing a lot of her growing up. And then in 2019 we had our second child and that even more so (closed the door).”

One of the teams that reached out to Middlebrooks about coaching in their farm system was the Red Sox. Middlebrooks formed close connections with the organization after being drafted by Boston in 2007 and spent parts of three seasons from 2012-14 in the big leagues with the Red Sox.

“There were some talks. There was never like anything on the table that was like a deal, like here’s an offer,” Middlebrooks said. “But the door was always open if I wanted to because just the relationships I have over here with people that are in the front office from when I was here as a player. The door was always open for discussion on that and if I pursued that profession, I think, yeah, I would have probably wanted to coach for the Red Sox.”

It seems like if the 35-year-old Middlebrooks had a change of heart and wanted to give coaching a try for a big league organization, he could. Perhaps even with Boston since his former teammate Craig Breslow is the Red Sox chief baseball officer.

But after carving out a successful media career, Middlebrooks is content and coaching is no longer on his radar.

“It’s not a grind I wanted to go through again,” Middlebrooks said. “I love teaching, I love talking about the game, but the hours you put in as a coach, if you want to be a good one, it’s a lot. I’m happy where I’m at right now.”