How Jenny Dell pushed Will Middlebrooks to get into TV

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Will Middlebrooks is great in the TV studio. The former Red Sox third baseman is funny and insightful — an exceedingly rare combination. It seems like he could enjoy a long and successful career behind the mic.

He has his wife to thank.

In a recent interview with Barrett Sports Media, Middlebrooks says Jenny Dell, whom he married in 2016, pushed him in front of the camera after a serious leg injury led to his abrupt retirement in 2019. At the time, Middlebrooks wanted nothing to do with baseball.

But Dell, the former Red Sox sideline reporter who now works for CBS Sports, already set up her husband with an interview at her network. Her persistence paid off.

“She said, 'Well, I don’t care. I already told them that said you would do it,’” Middlebrooks said. “So she kind of threw me to the wolves, but for the best. And I went in and I gritted my teeth and just got it done and then talked baseball. I did it a couple of more times and they said, ‘Hey, you’re decent at this. We’re going to hire you on for a year!’ And here we are, I’m four years into it.”

Middlebrooks was one of the Red Sox’ top prospects in the early 2010s, serving as one of the few bright spots during their disastrous 2012 campaign (he slashed .288/.325/.509 with 15 home runs in 286 plate appearances). But he was never able to build on his impressive debut. Middlebrooks posted a .611 OPS over the next five seasons, three of which were played for the Padres, Brewers and Rangers.

After suffering his devastating knee injury, Middlebrooks, 33, says he sat around and “sulked” for three months. It’s a trap of self-loathing that many ex-athletes can fall into.

It’s fair to say Middlebrooks has snapped out of his malaise. He boasts more than 155,000 followers on his very active Twitter feed, and plays double duty with CBS Sports and NESN. Middlebrooks will be in the NESN pre- and pos-game studio for 40 games this season.

“If I was going to work for an organization or a regional sports network, why not the Red Sox, for someone that I’m actually a fan of?” he told Barrett Sports Media.

NESN viewers are certainly fans of him.