Forced to retire from baseball early, Will Middlebrooks now has a budding second career

"One day when I’m old and gray, I know I’m not going to look back and wish I spent more time in baseball."

Matthew J. Lee
Will Middlebrooks hit 17 home runs for the Red Sox in 2013, and helped them win the World Series that year.

Had certain plot twists gone a different way, Will Middlebrooks might still be playing for the Boston Red Sox.

It was eight years ago — yes, that long now — that he arrived at age 23 as a welcome summer phenom with a floundering 2012 Red Sox team, hitting 15 home runs in 75 games.

A year later, he was the primary third baseman on the beloved “Boston Strong” World Series champions, hitting 17 home runs. But struggles at the plate late that season plagued him through 2014, and he was traded that December to the Padres.

Three organizations (Brewers, Rangers, Phillies) later, he suffered a horrific leg injury during a collision with a teammate in 2018 spring training with the Phillies, breaking his fibula among other damage. After several surgeries and too much pain, he retired in the spring of 2019.

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Middlebrooks turns 32 on Wednesday, still a young man by life’s parameters and one who might be in the back end of his prime had baseball gone differently.

But there are no laments for him, just good-natured candor about how it all played out, as he pursues a second career he enjoys while spending as much time as possible with those he loves.

“One day when I’m old and gray, I know I’m not going to look back and wish I spent more time in baseball,’’ said Middlebrooks, who is in his second year as a baseball analyst for CBS Sports HQ, the network’s streaming service. “I’m going to look back and be glad that I spent as much time as I could with my family.”

Middlebrooks and his wife, former NESN Red Sox reporter Jenny Dell, are the parents of two young daughters. The eldest, Maddie, turns 2 next month, while the youngest, Makenzie, is 8 months. With Dell currently away for a college football assignment, Middlebrooks is home with the girls, squeezing in an interview Friday while they were taking a nap.

“I’m just I’m so lucky to be able to be here and allow Jenny to keep doing what she wants to do,’’ said Middlebrooks. “Because if I was gone, she might have to really put the brakes on shooting her show. I’m able to be here and still work, and it’s worked out perfectly.”

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Middlebrooks shoots his segments for CBS Sports HQ from a setup in the front room of their Boynton Beach, Fla., home. He comes across as a natural on camera — funny, fair, and plugged in to the current game — but he says it was anything but easy at first.

“I never really thought about getting to the TV side of things,’’ said Middlebrooks, who figured he would go into coaching like his father, Tom, a football coach in Texarkana, Texas, for 40 years. “Jenny worked for CBS and said, ‘You know, my boss is asking if you would just want to try it,’ and I was like, ‘Heck, no, that’s not for me. I’m fresh out of the game.’ I don’t want to have to be put in a weird spot to talk about guys who might have been my peers in a negative way. Because I don’t ever want to be that guy who forgot how hard the game was.”

He pauses and laughs. “Which is impossible anyway. Look at the back of my baseball card. It was hard.”

Still, Middlebrooks followed his wife’s advice to give it a shot, and despite being “super nervous,’’ he got the gig last spring. “CBS gave me a chance to not be perfect and just learn,’’ he said. “And I’m still learning.”

Middlebrooks acknowledges it wasn’t easy, even after retiring, to come to grips with no longer being a player.

“It was tough to start,’’ he said. “One of the reasons I was hesitant to get into it was because I still had a really bad taste in my mouth from breaking my leg and all the surgeries and on how it ended. But the more I got into the job, it almost turned into therapy for me.”

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Middlebrooks’s sports media future is bright. He is already better on camera than many ex-player analysts that hold higher-profile network roles. He’s also a stalwart on social media (@middlebrooks on Twitter), one of a lineup of recently retired players — among them Brandon McCarthy, Trevor Plouffe, and Phil Hughes — who are adept at engaging with fans, often humorously.

“I enjoy Twitter,’’ said Middlebrooks. “I love it. Jenny thinks I’m crazy. She’s like, ‘You interact with way too many of the wrong people.’ I interact with a lot of the right people, too. I get it, but it’s the thing with social media. No one has to answer to anyone. There are no consequences. You can’t get punched in the face. You can say whatever you want. So if I have 150,000 followers, which comes from me playing in Boston for a big-market team, and I have a chance to highlight what you’re saying and how awful you’re being and have other people yell at you, maybe you’ll think twice about it. Probably not, but that’s just my way of approaching it.”

He doesn’t shy away from sharing his views on politics and social matters, either. Any assumptions about a white ballplayer that grew up in Texas and lives in Florida should not be made.

“The racial injustice, I will never put up with that,’’ he said. “Where I went to high school was 60 percent African-American students. I heard a lot of things from fans to high school kids at basketball games and baseball games and things being said, and this is in the early 2000s. It’s not like it was 1950. And this stuff is happening to my closest friends and my teammates. It just stuck with me. I always told myself I would pride myself on taking up for people who were treated badly for the color of their skin.”

Middlebrooks has had offers to coach in the minors, but he intends to keep on with the budding media career, keep taking down the trolls on Twitter, and keep being there for his wife and daughters.

“I’m going to keep going with the flow and see what happens,’’ he said of his media career. “I love talking about baseball, and who wouldn’t want to do that? And I love being home with my family.

“The end of my career, in some way you could call it a blessing in disguise. Even if it was a hell of a disguise.”

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