Boston Red Sox radio announcer Will Flemming recently found himself in hot water following some over-the-top commentary about Jazz Chisholm Jr.
In the wake of that, Boston Globe sports columnist Chad Finn made an ask of Flemming: Stop trying to sound like you’re doing a podcast.
In a column published Saturday titled “Will Flemming should approach his radio broadcasts differently, and treat them less like a podcast,” Finn says that the backlash the Red Sox announcer received for saying Chisholm was a “bush-league player” and that Boston pitcher Jovani Morán “should fight Chisholm” for stealing bases in a blowout was “deserved.”
Flemming did apologize to the Yankees and manager Aaron Boone, though not to Chisholm directly (and the New York Yankees star wasn’t interested in hearing from him anyway). However, Finn says the incident “crystallized a bigger problem” that he’s been hearing about from readers all season long.
“Way too often, the broadcast sounds like it could be called the World of Will Flemming Podcast, or perhaps the realization of the opinionated sports-radio-show approach to a game broadcast that the then-WEEI morning show hosts pushed for several years ago,” wrote Finn. “Flemming sounds like he’s aiming to appeal to the popular Section 10 podcast hosts and listeners rather than the demographics of the audience most likely to listen to a game on the radio. He overflows with hyperbole — if Joe Castiglione’s slogan was “Can you believe it?” Flemming’s might be “That just can’t happen!’’ when a Red Sox player commits a gaffe. The ambient noise of a radio baseball broadcast is buried in adverbs. The game is not allowed to breathe.”
As Finn notes, Flemming tends to take over the call of the game to rant about unrelated topics, often leaving his analyst partner in the booth with limited opportunity to speak.
While the sports columnist praises Flemming, who has been part of the Red Sox booth since 2019, for his voice and conversational rapport, he says he’s inundated with complaints about his style, including a penchant for telling listeners what he anticipates will happen, which leads to errors and misjudgment when he’s wrong.
Finn received some pushback on his column on social media, but responded by saying that he’s never received more negative feedback about a Red Sox announcer in the 18 years he’s been covering them.
Further, I’ve been covering sports media in this market for 18 years. The gripes about Flemming this season exceed any I’ve received about any local broadcaster over the totality of their careers.
— Chad Finn (@chadfinn.bsky.social) September 5, 2026 at 10:19 AM
Flemming and the Red Sox booth finished 8th in Awful Announcing’s 2026 local MLB radio broadcasters rankings, so they definitely have their fans, though readers certainly had some criticisms of Flemming (can be “a bit generic” or “overly dramatic on routine plays ”) as well.

About Sean Keeley
Along with writing for Awful Announcing and The Comeback, Sean is the Managing Editor for Comeback Media. Previously, he created the Syracuse blog Troy Nunes Is An Absolute Magician and wrote 'How To Grow An Orange: The Right Way to Brainwash Your Child Into Rooting for Syracuse.' He has also written non-Syracuse-related things for SB Nation, Curbed, and other outlets. He currently lives in Seattle where he is complaining about bagels. Send tips/comments/complaints to sean@thecomeback.com.
Recent Posts
Richard Sherman casts doubt on Joey Porter Jr. illness
"I think maybe if they would have gave him a new contract, maybe he would have been a little healthier today."
Jane Slater starstruck by Lainey Wilson during ‘SportsCenter’ segment
"She's essentially my Dolly Parton, guys."
Dianna Russini reportedly hires crisis publicist as comeback awaits
Dianna Russini has hired one of Hollywood's most notorious crisis management experts as she prepares for a potential comeback.
Bill Simmons curses out ESPN for deleting Grantland recordings
"So they can go eat a big fat d*ck."
Legendary NFL player, coach, analyst Mike Ditka passes away at 86
Mike Ditka passed away on Friday after an incredible career in football as a College and Pro Hall of Famer.
Cowboys-Bucs was not a great night for Al Michaels
Al Michaels is a multi-generational legend as a broadcaster, but Thursday Night Football's Cowboys-Bucs game was another rough night.