How Rich Shertenlieb Turned a Career Setback Into a Boston Sports Radio Comeback at WEEI

That personal connection is something Shertenlieb has learned is vital to success. Just weeks after launching the program on WEEI, he has already developed an appreciation for his team and the station staff. He admits he is loyal to a fault with the people around him as he continues building what he hopes becomes a legitimate competitor in the daypart.

Despite the obvious ratings challenge against an established competitor, Shertenlieb understands success is not earned overnight.

“The one thing about a new show, it takes reps to get things correct. Every show that I’ve ever launched, the first six months are just a mumbled mess because you’re developing that chemistry,” said Shertenlieb.

Approach Is Everything

The content approach is simple: sports-first, but with the fun and authenticity Boston sports fans crave.

“I’m not going to go over WAR stats on a series that nobody cares about in the middle of July. I just can’t do that,” explained Shertenlieb. “If I don’t care, I can’t fake caring about it. It’s been a flaw of mine. I can’t come up with fake takes, because I’m not smart enough to remember them.”

Shertenlieb said he respects the longevity and success of his new direct competition at his former radio home. He complimented the success of Mike Felger and Tony Massarotti, referring to them as a “juggernaut” of a program, and refused to trash their product.

However, for Shertenlieb, a win for WEEI’s afternoon program means more than ratings alone.

“I don’t care about the ratings for the first six months to a year. That is the time with the launch of every show that you’re still developing. You’re not what you’re going to be. That takes time to get everything gelled the right way,” noted Shertenlieb. “My success is having a station and show that can ignore the noise for the first year. After that, hopefully continue to find growth in every metric, every single book and week.”

That mindset also guided Shertenlieb during his morning show run on WZLX in Boston. During the six months the program lasted, he said he was proud of the growth the show experienced, something he hopes continues with WEEI.

“During that short time, we took that morning show from 14th place to 5th place. It was sad that it ended so soon because the trajectory over the last month was excellent,” said Shertenlieb. “I’m really proud of that time, but it’s all for the better. Now, I get to work with Mike Thomas again. To me, that’s probably the best part of all of this.”

Inspiration To Try Again

There’s no denying Shertenlieb’s passion for sports radio and entertaining Boston sports fans. That passion stems from a deeply personal place. Shertenlieb’s wife, Mary, has battled a rare form of leukemia four separate times over the last 13 years. Throughout that time, Shertenlieb has witnessed her fight firsthand, gaining a perspective he has applied to both his life and career.

“It’s only gotten clearer in what’s truly important,” explained Shertenlieb. “It also helps me appreciate the opportunity to talk about millionaires bouncing a ball for four hours with my friends. I’m so grateful, because I know there’s people that would give anything to just be outside of a hospital. For me, to complain about the Alex Cora firing for a living is such a gift.”

As his wife’s battle continues, Shertenlieb has become a major supporter of the Dana-Farber Cancer Institute and the annual Jimmy Fund, which supports cancer research. Even while part of the 98.5 The Sports Hub lineup, Shertenlieb said he was jealous of WEEI’s role in the annual fundraiser and even found time to cross-promote the effort while working for the station’s competitor.

Now, Shertenlieb looks forward to playing a major role in the annual event with WEEI and hopes to help set a new fundraising record later this summer.

“The fact that I get to be one of the major voices of that telethon and say what it’s like from the inside with a family member going through it. It’s an absolute honor, and I couldn’t be more excited about the opportunity,” said Shertenlieb. “They’re going to have to pull me off the air. I’m going to be obnoxious and want to stay on the air for the entire 48 hours of the event.”

In many ways, Rich Shertenlieb’s return to Boston sports radio feels less like a comeback story and more like a reminder that longevity in this business is never solely about ratings books, viral clips, or winning a head-to-head battle. It’s about perspective.

After career highs, unexpected setbacks, and years spent watching his wife battle cancer with unimaginable strength, Shertenlieb has arrived at a place where authenticity and genuine connection matter more than performative noise.

That perspective may ultimately become WEEI’s greatest advantage. Shertenlieb isn’t entering afternoons trying to recreate the past or tear down the competition. He’s entering the role understanding that chemistry takes time, trust requires patience, and success is built one show at a time.

For Shertenlieb, this opportunity is bigger than simply returning to sports radio. It’s about reconnecting with a format he loves, teammates he trusts, and a city whose sports culture helped shape his career.

Barrett Media produces daily content on the music, news, and sports media industries.Sign upfor our newsletters to stay updated and get the latest information right in your inbox.

John Mamola

John Mamola

John Mamola is Barrett Media’s sports editor and daily sports columnist. He brings over two decades of experience (Chicago, Tampa/St Petersburg) in the broadcast industry with expertise in brand management, sales, promotions, producing, imaging, hosting, talent coaching, talent development, web development, social media strategy and design, video production, creative writing, partnership building, communication/networking with a long track record of growth and success. He is a five-time recognized top 20 program director in a major market via Barrett Medi’s Top 20 series and has been honored internally multiple times as station/brand of the year (Tampa, FL) and employee of the month (Tampa, FL) by iHeartMedia. Connect with John by email at John@BarrettMedia.com.

linktr.ee/johnmamola

The post How Rich Shertenlieb Turned a Career Setback Into a Boston Sports Radio Comeback at WEEI appeared first on Barrett Media.