Greg Hill is Turning the Tables in Morning Drive on WEEI | Barrett Media (2024)

Earlier in the week, the Boston Celtics secured their 18th NBA championship. Across a variety of sports radio stations, especially those in the Boston-Manchester designated market area, the triumph was a subject of discussion on Tuesday morning. Within morning drive on WEEI, host Greg Hill provided his thoughts on the team and its achievement.

Akin to the Celtics, Hill aims to position his weekday program to thrive and sustain success. After working in the industry for many years, some professionals can exhibit a sense of apathy, but for Hill, it is quite the opposite, exhibiting congeniality and authenticity to the audience as a whole amid this quest.

Although Hill broadcasts on a sports talk station, the morning show spans beyond comprehensive sports discussion while implementing a variety of other topics into its daily discussion. In fact, Hill defines the breadth of topics into two distinctive categories, one of which is sports while the other covers an assortment of miscellaneous subjects mentioned on the show.

“I think it’s more beneficial if you are a radio person and you know what you think works when it comes to doing radio,” Hill said. “If you can find a way to keep the audience entertained and engaged and try, if you can, to present content that’s different than [what] they might find somewhere else, then that’s more important than necessarily a vast X’s and O’s knowledge when it comes to sports from my perspective.”

Sports teams in the city of Boston have established a tradition of grandeur and excellence, making a habit of remaining in contention for championships every year. In fact, the Celtics championship ended the city’s title drought that spanned just over five years. During that time, the media ecosystem has changed with a prioritization on digital distribution in addition to more niche content offerings. As a long-tenured radio host, Hill has been able to successfully adapt by optimizing the idiosyncrasies of the medium while also being open to innovation.

“The old adage about, and I think it still remains a unique advantage when it comes to this medium, is that when you wake up in the morning, you want to know, ‘What happened? What happened last night?,’ and you want to hear people give you their slant on it,” Hill said. “My function, I think, is to give everybody the opportunity to share their opinions on stuff.”

While Hill has become a respected sports radio host, he initially started working in another sector of the industry. During his time as a middle school student, he worked a paper route and saved his money to buy two turntables and several 45-rpm records. Hill would then go to the garage of his parents’ house and host a radio show with no audience, working to master the craft in his nascence. As he grew older, he started to bring his records to his high school radio station and take the air.

The passion and verve he possessed for the medium, along with his talent in the craft, helped him land a job at WAAF as a promotion coordinator. As he began to showcase his abilities, he earned chances to go on the air over the weekends and overnight. Morning show host Drew Lane later asked Hill if he wanted to do sports on the program, and he continued to grow from there.

When Hill was named the host of the new Hill-Man Morning Show on WAAF a few years later, he needed to find a way to stand out in the marketplace. After all, he was facing competition from Charles Laquidara on WBCN and a variety of other media outlets, and it took time for the program to eventually break through. Hill took the opposite approach of other stations in the area to render the show distinct from those on other media outlets.

“WBCN at the time was an older-targeted station, so we targeted the station towards Men 18-34 and figured that we could grow as they grew,” Hill said. “So we were just going out attending every single possible event where somebody might be, going out before concerts and shaking hands, and doing all that stuff that I think you have to do in order to try to get people to try your show and try your station.”

Hill’s program catapulted to the top of the marketplace, and he signed a lifetime contract after 26 years on the air to stay at WAAF. In signing the deal, he never thought he would work anywhere else, but things changed three years later when Gerry Callahan hosted his last show in morning drive on WEEI. Then-Entercom announced that it was adding Hill to the daypart to host a new morning drive program and retained co-host Danielle Murr in the process, commencing a new era for the outlet. Shortly thereafter, WAAF was sold to the Educational Media Foundation and re-formatted with contemporary Christian programming.

“I never thought [W]AAF would go away,” Hill said. “It was a legendary rock station, and I still to this day will flip by that station and hear Christian rock music and sit there in silence for a couple of minutes for that great radio station, but being the same company and the same market manager at the time [in] Mark Hannon, when that opportunity came up [to] try something different and to make a change, I was really excited about it.”

In moving formats, Hill and his colleagues evaluated the program and determined how they could grow their audience on WEEI while staying true to the essence of the show. The program, however, was going up against Toucher & Rich, the hit morning show on 98.5 The Sports Hub, and others.

“I think this business is slowly moving farther and farther away from dollars being dependent on being the #1 station or where you’re ranked when it comes to Nielsen,” Hill said. “To me, the most important thing is that we’re doing what we should do to get partners for the radio station on the business side of things and delivering results for them.”

Hill is cognizant of the success of 98.5 The Sports Hub but articulated that the ranking does not matter to those spending money on radio. Instead, he claims that it is about the level of engagement and patronization of the product that facilitates interest in the brand.

“From a differentiator point of view, we’re up against, on the sports side of things, an incredible radio station that has done an amazing job of being #1 in this market for a long time with really compelling personalities,” Hill said. “I think it’s incumbent upon us to try to find ways to be different when it comes to our choice on content and the way in which we present it, and then outwork them when it comes to going out and meeting people who might listen to the show.”

Whereas Hill was originally a solo host during his early days on WAAF, he is now joined by Jermaine Wiggins and Courtney Cox, both of whom bring unique aspects that enhance the program. Wiggins, a former tight end for the New England Patriots, provides his knowledge of football and the perspective of a professional athlete. Cox is the youngest person on the program and has a unique approach from her time covering sports at NESN while embracing the humor and repartee on the show. Show producer Chris Curtis, who worked with Hill at WAAF, also contributes to the conversation as well and has helped maintain synergy.

“Whether it’s the co-hosts on the show or callers, I love when they are having fun at my expense, and I think that self-deprecating humor to me is the best,” shared Hill. “If we have a show in which I end up being the punchline or end up, whether it’s my age or lack of technological skill or my frugality – whatever it is – that to me is my favorite part of what we do and that personality coming through, I guess.”

Hill uses his platform to benefit the community through The Greg Hill Foundation, a nonprofit organization he founded to provide families affected by tragedy with immediate needs. He created the foundation in 2010 to celebrate two decades on the air at WAAF before the advent of crowdfunding in a quest to give back. The foundation has donated over $20 million to more than 9,000 beneficiaries during its 14 years.

“We’re lucky in radio because we have this incredible tradition of public service, and I think everybody in radio feels this obligation – this great obligation to use the airwaves to help others,” Hill said. “We’re granted the incredible platform in which we can actually get people to respond when help is needed, and so I wanted to be able to use that microphone and the radio station on those days to be able to help the beneficiaries in our area who needed it.”

Hill recently signed a multiyear contract extension with Audacy-owned WEEI to continue hosting The Greg Hill Show. Part of what compelled him to remain at the station was working with Ken Laird, the brand manager of the outlet who used to be his producer at WAAF. Moreover, he has known Audacy Boston market manager Mike Thomas for over two decades as he leads the cluster of stations in an environment with many entities looking to garner shares of attention.

“To be able to have the opportunity to work with those guys, know what they are, what I need them to do to keep them happy and to have the opportunity for us to, from a team perspective, that we have one clear mission in mind, and that is to be No. 1,” Hill said. “No. 1 in revenue and No. 1 when it comes to ratings, so to be able to sit there and go, ‘Alright, since I came here five years ago, we definitely have some wins, but there’s still a lot that we have to do,’ and to be able to do it with them together was way more interesting to me than any other opportunity.”

Even though Hill has worked in the sports media business for many years, he remains energized by the prospect of achieving goals and having the privilege to host his radio program. In the past, he has stated that he would like to slow down in his career, yet he is unsure what he would do without working in radio.

“That being said, I’ve been getting up at the crack of dawn for 30-something years, and I’m definitely feeling it more than I used to,” Hill said. “But sometimes I think it would be fun to go and do one more radio show where I play seven great songs an hour, as long as I get to pick whatever I play and there’s no research and there’s no computer programming the music. I sometimes think about that, but I just love doing this.”