Will Flemming excited to answer the call in Red Sox’ radio booth
The 45-year-old broadcaster is sliding into the spot left when Joe Castiglione retired after 42 years.
When checking in with Will Flemming to ask how he feels about his official role as the radio play-by-play voice of the Red Sox, it feels right to frame the question in the famous words of his friend, former broadcast partner, and advocate, Hall of Famer Joe Castiglione.
So, Will . . . can you believe it?
“I mean, we’re talking about the Red Sox,‘’ said the 45-year-old Flemming, who slides into the retired Castiglione’s lead spot after six years as part of the radio broadcast team, during a conversation in advance of Thursday’s season opener at the Texas Rangers.
“We are talking about Joe Castiglione and Curt Gowdy and Ken Coleman, legends of this business.
“This is something I’ve been working for and toward for a long time, and I sit here . . . it’s almost impossible to put into words, the emotion that I feel. [This is the] start of my life as the voice of the Red Sox. Yeah, that’s cool.”
Flemming has paid his dues in full. He briefly worked in Silicon Valley after graduating from Stanford, but the dream of being a baseball play-by-play broadcaster — which is something of the family business now, with his older brother Dave entering his 22nd full-time season as part of the San Francisco Giants’ radio and television broadcast teams — did not stop beckoning.
In 2009, he took a $500-a-month job calling home games for the Astros’ Single A team in Lancaster, Calif. After nine seasons in the minors, he made his big league debut in the Red Sox radio booth in 2019, when WEEI had the ridiculous notion to use a rotating and mostly unfamiliar cast of broadcasters with Castiglione in 2019.
Flemming survived that chaos, as well as a murky offseason following the 2023 season when WEEI, dealing with parent company Audacy’s financial straits and the knowledge that the Red Sox would oversee the broadcasts beginning in 2025, offered him just a one-year deal. He was a candidate for openings with the Tigers and White Sox but ended up sticking around.
It was the wise move. Castiglione decided to retire after 42 years in the booth (though he will make occasional appearances this season) and advocated for Flemming as his successor, on and off the air.
“Last year was such a mixture of emotions for me because I listened to him tell the world that I should have his job,‘’ said Flemming. “It was an incredibly powerful thing, but at the same time it wasn’t surprising because that’s how he treated me from the moment I walked into that booth.
“Some people in town and some media got on me for crying when he was signing off last year. I couldn’t care less about that. To have him say goodbye and then pass the baton to me, I don’t know how any human being couldn’t be emotional about that. I’m not ashamed that it moved me in a way that it did.”
Flemming, like Castiglione, is easygoing as a broadcaster, but he has his own style and approach.
“As someone who worked with Joe and watched him be the perfect voice for New England and representative of the team, I understand everything he means and the special connection he had with fans for 42 years,‘’ said Flemming. “I feel so lucky that he showed me the way to connect with people and he showed me the things fans care about.
“It’s an awesome kind of responsibility to follow him and carry on his legacy, but I’m also so excited to put my own stamp on it. And I feel like the six years I sat next to Joe made me as ready as I can ever be. I’m not trying to be Joe. There’s only one of him, right?
“He is so unique. I will never have his encyclopedic memory. I will never be exactly what Joe was. I’ll do it in a different way than Joe, because we’re all different broadcasters, but I will honor his legacy.”
Flemming will most often work with former Red Sox third baseman Will Middlebrooks, who will be the analyst for at least 70 radio broadcasts. (I imagine their marketing department is working on “Will and Will” branding as you read this.)
Flemming said he feels they have already built a rapport.
“Chemistry is a really hard thing to find in any broadcast media,‘’ said Flemming. “Will and I have been friends for the last three years, but you never know until you actually do a game whether you see it the same way.
“And within five minutes of doing our first spring game, I said to myself, ‘This is fabulous and we’re going to have a great time.’ ”
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