As the holiday season continues with Christmas just around the corner, there’s a familiar buzz in New England. A feeling so reminiscent it echoes past glory—when Brady and Belichick once ruled America’s new pastime and the New England Patriots dynasty was underway. WEEI’s Greg Hill remembers the good times of six Super Bowl championships in less than two decades.
“I get accused all the time of throwing the dynasty term around too freely, but I’m all in on it,” says Hill. “We took a four-year break to re-charge, and now we’re right back to where we were… It’s awesome for sports radio in Boston.”
Hill has been a guiding voice for Bostonians for over three decades. Following a successful 28-year career in mornings at the legendary rocker WAAF, Hill transitioned to sports talk in 2019. At WEEI, Hill followed longtime sports radio talker Gerry Callahan as the morning voice waking up Boston sports fans—a fanbase known for its passion and demand for excellence.
For Hill, it was a new opportunity to connect with the Boston morning drive listener. Now, seven years into his tenure at WEEI, it’s exactly where he wants to be, doing what he has always wanted to do.
“Getting to be there when it comes to being a part of our listener’s lives. Being able to do that for a long time is something I never imagined,” says Hill. “Other than waking up early in the morning, it’s the best job there is.”
Radio was Hill’s dream from his youth. A native of the Boston area, he cracks the mic every morning on WEEI with his teammates Jermaine Wiggins and Courtney Cox. The Greg Hill Show can be described as a melting pot of information, opinion, and entertainment, with three different backgrounds presenting the content.
The goal is the same: always finding new ways to connect with Boston sports fans. Every morning, contributions from all team members are included in the execution.
“Courtney and I get in here before the show and gather what we’re thinking from a news perspective. Jermaine is an East Boston guy, and he has no filter, which is awesome,” noted Hill. “Some shows spend a lot of time discussing how someone may feel about certain topics ahead of time. We don’t do that till the microphones are on.”
The Patriot Way
A unique characteristic of The Greg Hill Show is the exclusivity it provides. While WEEI is not the New England Patriots’ flagship station, it holds exclusive rights to interviews with key franchise figures. The Greg Hill Show began in 2019, at the tail end of the Brady/Belichick era, featuring exclusive interviews with both personalities.
Hill noted that both Brady and Belichick in that final year together were “miserable,” and the interviews didn’t provide much content for the sports fan. However, this season, with new head coach Mike Vrabel, the content has a much different feel.
“Bill [Belichick], part of the allure with him was he was just kind of a ‘dink.’ Not just with us, but with everybody,” explained Hill. “With Bill, you had to work hard to ask around a question, then to get an answer that you needed to translate to see what he was really saying. With Mike Vrabel… I think this happens sometimes when you end up being away from the job you love for a while, you’re excited about being back there. He enjoys being on with us.”
He called the interview experience with Vrabel “much better” than with Belichick, though he noted Belichick is considered the greatest coach of all time. Access to both coaches holds immense value for any morning show. It allows the show to serve as an exclusive conduit for fans, as Hill experiences every week.
While many traditional radio stations would consider the exclusive interview a massive appointment tune-in, Hill noted that how content is consumed no longer matters.
“The biggest change in this business is it’s always been a content business. Finally, this industry is getting smarter about it. It doesn’t matter the platform the content is consumed on. The content is always king,” said Hill. “However it’s consumed from my perspective is irrelevant. It doesn’t matter to me as long as people find what we do.”
Redefining Success
The demand for content is at an all-time high. Boston sports radio has delivered some of the most appealing sports content for many years. On-demand content may not always count toward ratings, yet WEEI and 98.5 The Sports Hub continue to dominate Boston’s rating share. WEEI has not always ranked as high as its competition. For Hill, however, ratings are not the only metric that defines winning.
“I’m fortunate to work for a company where the people in charge have figured out that revenue is the most important thing,” said Hill. “For a long time in this business, I guess revenue was tied to a ratings point. For me, what I’m excited about is what we’re doing when we’re working with our partners… If we go year over year and grow from a revenue perspective, I’m ecstatic.”
Hill credits that focused mindset to working under Audacy Boston market manager Mike Thomas, who joined the company in 2021. Thomas, who helped launch the competition at 98.5 The Sports Hub, brought his programming background and understood the challenges of the role Hill was serving.
“It’s great to have a market manager who has a programming background. It’s rare for me, and probably the first time that’s happened in 36 years,” explained Hill. “He has a ton of input, which is good stuff from a programming philosophy and tons of ideas. He’s someone who understands, from a talent point of view, the challenges of every day including with sales… It’s refreshing to have his approach to that as well, working with talent.”
The support and connection Hill has built with Thomas have helped guide the program to new levels of success. They focus on reaching new listeners every day.
Connecting With Those in Need
Another element of Hill’s connection with Boston is through his efforts with the Greg Hill Foundation, which he founded in 2010. The mission was simple: use the megaphone and the power radio has with the community it serves to respond to the immediate needs of families touched by tragedy.
“I wanted to create a way that we could turn the mic on at 6 a.m. and if something bad happened that people were talking about, we could find a way to help immediately,” said Hill. “We live in the most generous part of the country. We have great partners who donate a lot of money, but we also get small donations that come from people who give over and over again.”
To date, the Greg Hill Foundation has raised over $31 million, helping more than ten thousand people in need in the Boston area. From wine-and-dine events to the annual Jingle All The Way 5K and everything in between, Hill’s love for radio has been supported by his teammates at WEEI.
“It’s one of the great things about this business that separates us from content being available everywhere. Radio has always been a medium that gives back to the community,” explained Hill. “Radio is uniquely able to help the community it serves. We do it, and people give immediately. It’s an amazing thing.”
For nearly four decades in Boston, Hill has aimed to connect with his community. Whether walking around town, sharing a beer at the bar, or raising money, he engages with people and supports those in need. Greg Hill has made it his mission to find connection in a content space that becomes ever more fractured.
“I am so fortunate to love what I do, and to do it for a long time. I’d never want to stop,” said Hill. “I don’t know what else I would do. I’m not qualified for anything else and would miss the opportunity to talk to people and connect. I would miss that… I’m probably not going anywhere unless they kick me out of here.”
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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.
No one works harder than Greg Hill, full stop. There’s never a barrier he won’t overcome, never a listener he won’t connect with, never a client he won’t make the time for to help the organization achieve its goals. He’s professional, approachable, and always willing to roll up his sleeves and get it done. That mentality and his work ethic applied liberally over a few decades have ensured that he is a star and that he matters to Boston Radio.
I have been a listener of Greg’s since the late 90’s on my car ride to high school. After college in 2004 I had to buy fancy radios and external add on antennas to get AAF on in the lab I was working at in Woburn. Once the iPhone was a thing, I had to find an app that would let me stream and even record the show! (OoTunes) – yes it sounds like an addiction but it’s the first four hour of my day, like coffee, interrupt me at your own risk! I will admit it took a couple years to get over the loss of my beloved WAAF and adjust to the station change but I’m back in the saddle, 4hrs a day, streamed mostly via YouTube ❤️
Keep up the great work team!!