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Will Flemming a pleasure to listen to on WEEI’s Red Sox broadcasts

Will Flemming (right) and Joe Castiglione are calling Red Sox home games this season from their familiar perch at Fenway Park.Jim Davis/Globe Staff

Of all the broadcasts I have watched and heard as the sports leagues have relaunched, the most satisfying and authentic have been the Red Sox radio broadcasts on WEEI.

In these most abnormal of times, the broadcasts sound like they could come from any regular summer. I probably don’t have to say it, but that is welcome.

Now, I recognize that part of the reason the radio broadcasts sound so normal is because your eyes can’t contradict your ears like they do while watching a game on television. The ambient crowd noise on radio is unobtrusive, but the juxtaposition of hearing it on a television broadcast at the same time you’re seeing the 35,000-plus empty seats at Fenway Park can be hard to reconcile.


Most of the appeal of the broadcasts, even as the team is increasingly unappealing, is due to the work of Joe Castiglione and Will Flemming. Castiglione is the comfortable constant, having joined the Sox booth back in 1983, when current NESN broadcasters Dennis Eckersley and Jerry Remy were still players.

Flemming is newer to the scene, having been recalled from Pawtucket as part of the rotating cast of broadcasters WEEI used alongside Castiglione last year. (”I guess I won Broadcast Survivor last year,” joked Flemming.)

Down to call the vast majority of the 60 games this year, Flemming, who has a multiyear contract, has been a smooth fit alongside Castiglione.

Flemming brings an easygoing style, a self-deprecating sense of humor, great respect for Castiglione, and the welcome mind-set that baseball is supposed to be an escape, now more than ever.

“The fundamental job is to tell them what’s going on with the Red Sox, obviously,’' said Flemming, whose older brother, Dave, is a play-by-play broadcaster for the San Francisco Giants. “That’s why they’re listening. But the second track of it is people listen to baseball and all sports to be entertained and to escape their regular lives. And I think this year more than ever that is more important. I think that I consciously this season more than ever try to find the positive and happy in everything.


“And I also try consciously to not complain about the lack of fans, the weirdness. No one in the universe wants to hear me of all people, one of the 10 most lucky people in the world to be actually at Fenway Park, nobody wants to hear me complain about what we don’t have. It’s more important than ever that we stay positive and optimistic and focus on the blessing that is baseball while we have it.”

There are greater degrees of difficulty to calling games this season. Castiglione and Flemming (as well as Sean McDonough and Lou Merloni, when they are part of the broadcast) are situated in their familiar perch above and to the right of home plate during home games. But because radio broadcast teams are not allowed to travel per MLB mandate, they must call road games from a monitor in their Fenway booth. That can get tricky, not that Flemming is complaining.

“On radio, I think one of our most important jobs is to immediately react with the tone of our voice to tell the listener, ‘Hey, you might be on your back patio taking a drink, having a chat with your family, but right now J.D. Martinez just hit a ball that might well leave the ballpark.’ I think that’s really important to know within milliseconds of his contact. And that is much, much harder off of monitors.


“And so the home games, although the energy of a full park is not there and that part is missing, they feel somewhat similar. But on the road games off the monitor, it’s tougher to read the speed and trajectory of the ball, especially in the corners.

“My philosophy on that from the beginning has been, ‘We know we’re going to make mistakes. The best thing to do about it is not only admit it but then just to laugh at yourself about it.’ ”

Flemming’s perspective and gratitude he has for his job was shaped by life experience. His appreciation for being a Red Sox broadcaster comes from having had a past career — he began his work life in Silicon Valley in the world of tech startups after graduating from Stanford — that he discovered was not a passion.

“I realized that I just wouldn’t forgive myself if I didn’t pursue broadcasting one time for real,’' said Flemming, who with the support of his then-fiancée and now wife, Jennifer, decided to make the career change in 2009, landing a job for $500 a month to call home games for the Astros’ Single A team in Lancaster, Calif.

“It consumed me for the next 10 years and involved an enormous amount of sacrifice and would not have been possible without support from my family and my friends,’' he said. “There were many times that you think it might be the time to get off the road and go do something more practical and more reliable and more dependable.”


The next year, the Virginia native, who grew up listening to Jon Miller call Orioles games (Miller now shares the Giants booth with Dave Flemming), moved on to the Nationals’ Single A team in Potomac, Md. He spent two years there, then three with the Pirates’ Triple A team in Indianapolis. He beat out more than 100 candidates in 2015 for a coveted job with the Pawtucket Red Sox, which has been a pipeline to the majors for broadcasters, including his brother.

“Anyone who follows baseball broadcasting knows that getting a PawSox job is a major trajectory-changing moment,’' he said.

Flemming became familiar to Red Sox fans last year, hosting the pregame and postgame shows and often joining Castiglione and the other assorted broadcasters in the booth. Flemming was an especially good fit with Castiglione and McDonough, whose sharp sense of humor often targeted Flemming, leading to good-humored parrying.

Flemming’s role has expanded during this strangest of seasons. It’s one of the few positive developments related to the Red Sox in 2020.

“It’s definitely not what any of us would have expected,’' he said. “Yet I still feel a really profound sense of gratitude and honor to be a part of even in this strange environment. To be a part of people’s lives and hopefully to offer them some measure of escape. No matter how different and strange and challenging it is because of all the constraints placed on us, it’s still an amazing thing to be a part of it.”


Chad Finn can be reached at chad.finn@globe.com. Follow him on Twitter @GlobeChadFinn.