Brian Barrett is another unheralded talent in Boston offered an opportunity by Bill Simmons

Getty Images for Vanity Fair
Bill Simmons, pictured here in 2015, retains an uncanny knack for identifying talent in the Boston sports media. Getty Images for Vanity Fair

Bill Simmons left Boston for Los Angeles 20 years ago, embarking on what would become one of the most influential and successful media careers of a generation.

But all these years later and from that opposite coast, Simmons retains an uncanny knack for identifying unheralded talent in the Boston sports media and offering an opportunity to thrive.

Kevin O’Connor, the trustworthy NBA writer and podcaster for The Ringer, the podcast and media company of which Simmons is the founder and CEO, is one example.

Brian Barrett is about to be another.

Barrett, most often heard on weekends and as the Red Sox pregame and postgame host on WEEI the past few years, has been hired by Simmons to host a new Boston-specific podcast on The Ringer (now owned by Spotify.)


He gave his notice at WEEI Friday, and will be diving headlong into his new gig. The intention is to have the podcast launched later this month, before the Patriots begin their season.

“It’s crazy. I’ve known who Bill Simmons is for a long time … I grew up wanting to be in sports media,’’ said Barrett, 34. “And now they’re asking me to come and work for them. It’s unbelievable. I can’t tell you how excited I am about it.”

Barrett is not a household name in Boston media circles, but make no mistake, this is a terrific hire. The Peabody native and Syracuse graduate got plenty of reps in assorted time slots on WEEI since joining the station early in 2019 (his first show was in the 2 a.m.-6 a.m. window the morning after the Patriots beat the Rams in Super Bowl LIII), and he’s proven to be entertaining and informative without having to dabble in that scourge of sports radio, insincere hot takes. In short, he’s been a revelation.

He’s also the only sports radio host I can think of who uses analytics in an engaging way to enhance his opinions, such as pointing out that Franchy Cordero had an absurd 52 percent strikeout rate over a month’s time.


Barrett was on the air often at WEEI, but his name recognition and profile were still in the fledgling stages. It’s a credit to Simmons, whose origin story began when he built his own audience as The Boston Sports Guy at the now defunct Digital Cities site in the late ‘90s, for recognizing talent from afar in a relative upstart.

“Obviously this is an important podcast for me because it’s all my teams in the city I care about,’’ said Simmons. “I really wanted to find the right person and somebody that put thought into their angles but didn’t do the kind of negative stuff just to stir the pot and get a reaction.

“Can it be somebody that I learn from? Can it be somebody who’s entertaining? Can it be somebody who can mesh with the right guests?

“I heard a lot this summer. I was scouting everybody in Boston and he just kept jumping out. He could do stuff by himself, which is really valuable to us, but he’s really good with guests, too. The way he uses advanced metrics is really accessible and smart. He backs up every point he makes with data, but not in a super-nerdy way. He had everything we were looking for.”


The Ringer previously launched successful city-specific podcasts for New York (with John Jastremski hosting) and Chicago (hosted by Jason Goff) in 2021. The Boston podcast will follow the fundamental parameters set by those programs. There will be a minimum of three shows per week, including one recorded after each Patriots game.

There also will be “emergency” podcasts when breaking news or a big story occurs. The podcasts will be roughly an hour long, with Barrett doing an open before bringing in guests, which will include Simmons, O’Connor, and Ryen Russillo, all who have deep Boston roots.

“I’m excited because this is going to allow me to focus on certain things, and you don’t have to focus on four hours of content,’’ said Barrett. “It’s just getting one thing and making sure that one hour is really, really good.”

There’s also the opportunity to provide near-immediate quality content for an audience while it is still buzzing from a big game or event and interest is at a peak. That is perhaps the biggest advantage podcasts have over conventional sports radio.

“I think the advantage we have with the pods is the reaction time can be really fast, whereas in radio a lot of times their best people are not on after a Pats game,”’ said Simmons. “Or they’re not on after a huge Tuesday night Celtics game, right? They’ll dissect it the next day on the station’s best show, but not at 11 o’clock at night.


“Some of the opportunity for us is being there immediately when stuff happens, combined with the guests, combined with a host like Brian who is really smart about the Boston sports scene and has good angles and you can tell just [cares a lot.]

“One thing I noticed while scouting him is that some of his angles on slow sports days were really good. I remember on one of those weekend shows, they had a debate about who was more important to the second of three Patriots Super Bowl champions, Gronk [Rob Gronkowski] or [Julian] Edelman. It was the perfect topic in a situation like that, it didn’t get hot-takey, and it was really enjoyable.”

It was around that time Simmons made an offhand comment on his own podcast about how much he had enjoyed that WEEI weekend show, which included Barrett, Khari Thompson, and Nick “Fitzy” Stevens that day.

The hosts of the show excitedly noted Simmons’s praise the next time they were on the air.

Little did Barrett know then …

“When I heard that, I didn’t think that that meant they were interested in me or anything along those lines,” said Barrett. “At that time, I just thought it was a really cool compliment, to hear Bill Simmons say that.

“And now there’s this opportunity I’ve been working towards, to work with a Bill Simmons company, it’s unbelievable. This is what I’ve been trying to get to my whole career. I can’t tell you how happy and excited I am. It’s incredible to think about.”



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