Greg Hill: WEEI Morning Host, Contract Details, Net Worth, Career Timeline & Community Impact

Greg Hill is one of the most recognized voices in Boston radio. He hosts the morning show on WEEI, where thousands tune in each weekday for sports, news, and conversation. With a career that began in local radio over 30 years ago, Hill has built a strong reputation for consistency and connection with listeners. In 2023, he signed a new multi-year contract with WEEI, keeping him as the lead host of their top-rated morning program. 

His influence goes beyond radio, with active roles in business, digital media, and community support. This blog covers Greg Hill’s full story, including his background, career growth, contract details, earnings, and public impact. Every section is built to give a clear and complete view of who he is today.

Who is Greg Hill?

Greg Hill is a Boston-based radio host with over 30 years of experience. He leads the morning show on WEEI, where he talks about sports, news, and daily life. His voice is well-known across Massachusetts. Listeners trust his views and enjoy his easy, direct style. Outside of radio, Hill is also involved in business, charity work, and digital media.

Where Did Greg Hill Grow Up and Attend School?

Greg Hill was born and raised in Stow, Massachusetts. He attended Nashoba Regional High School, a public school located in nearby Bolton. This school serves students from several towns in central Massachusetts. Greg completed his high school education there, where he was known for being active and social. After graduating, Hill pursued further studies but specific details about his college attendance or degree have not been publicly confirmed. His roots in Massachusetts remained strong and helped shape his later work in local radio.

Where Does Greg Hill Live Today?

Greg Hill currently lives in the town of Framingham, Massachusetts. It is located about 20 miles west of Boston. Framingham is known for its suburban neighborhoods and strong community feel. Hill’s home is close to the WEEI studio, which makes his commute easier. Living in the Boston area allows him to stay connected with local sports, events, and the audience he serves. The location also places him near the headquarters of The Greg Hill Foundation and his business interests. His choice to stay local reflects his commitment to the region he has always called home.

Is Greg Hill Married and Does He Have Children?

Greg Hill is married. His wife’s name is Jennifer Hill. They have been together for many years and maintain a private family life away from public attention. The couple has children, although Greg does not share many personal details about them publicly. He prefers to keep his family matters separate from his career. Despite his visibility in the media, Hill rarely discusses his personal relationships on-air. This choice helps protect his family’s privacy while allowing him to stay focused on his professional work.

Did Greg Hill Play Sports in His Early Years?

While there are no official records of Greg Hill playing competitive sports in high school or college, he has long been involved with the local sports community. His deep knowledge of teams like the Red Sox and Patriots suggests he followed sports closely as a fan. Hill has never claimed to be a former athlete, but he often shares insights that reflect a lifetime of watching and learning about sports. This strong personal interest later played a big role in his radio career.

How Did His Interest in Broadcasting Begin?

Greg Hill’s passion for broadcasting began at a young age. He was fascinated by local radio and often listened to Boston stations as a teen. During high school, he became involved in event planning and audio production. These early activities helped him understand the technical side of media. After finishing school, he worked behind the scenes in promotions and production for local stations. This hands-on experience sparked his decision to pursue a full-time career in radio. It also gave him the confidence to eventually become an on-air personality.

Greg Hill’s Career Beginnings in Massachusetts Radio

Hill did not start in the spotlight. He entered radio through behind-the-scenes work and slowly moved toward hosting. Each early step helped him learn the industry from the inside out.

Greg Hill’s Early Radio Experience in Massachusetts

Greg Hill started his radio journey in Massachusetts in the early 1990s. He began working at WAAF, a well-known rock radio station based in Worcester. His first roles were not on-air. He worked in promotions and production, handling behind-the-scenes tasks that supported live shows. This entry point gave him real-world experience with radio systems, scheduling, and event planning. He was also involved in setting up remote broadcasts and live events across the region. Over time, Hill became more active in creative decisions, which helped him understand what listeners enjoyed.

What Was the Hill-Man Morning Show on WAAF?

The Hill-Man Morning Show was Greg Hill’s first major on-air success. It aired on WAAF and ran for over 20 years. The program mixed rock music, humor, and daily talk segments. It gained popularity for its bold and direct style, which matched the station’s rock audience.

Key features of the show included:

• Air time: Weekday mornings from 6 a.m. to 10 a.m.
  
• Content: Music, sports opinions, pop culture, live interviews
  
• Audience: Mostly adults aged 18 to 49 in the Boston area
  
• Tone: Candid, interactive, and edgy
  

The Hill-Man Morning Show helped Greg build a loyal listener base. It also gave him a reputation as a strong personality in Boston radio.

Key Lessons from His Early Career in Radio Promotions and Production

Greg Hill learned several skills during his time in radio promotions and production. These lessons shaped his approach as a host and leader. He understood the value of audience engagement and how to run events that connected stations with local communities. He also learned how to manage timing and technical problems during live shows.

Important lessons from this period included:

• Audience focus: Always create content that speaks directly to local interests
  
• Teamwork: Success in radio requires strong collaboration with producers and technicians
  
• Planning: Careful planning makes live events and shows run smoothly
  
• Flexibility: Adapting quickly during broadcasts keeps the audience engaged
  

These early lessons helped Hill later become one of Boston’s most consistent morning voices.

Greg Hill’s Rise as the Morning Host at WEEI

Joining WEEI was a major change for Hill after years in rock radio. It allowed him to focus more directly on sports and reach a new type of audience. His shift to WEEI helped him grow into a leading voice in Boston broadcasting.

Transitioning to WEEI and Becoming the Morning Show Host

Greg Hill officially joined WEEI in 2019 after leaving WAAF. The station, owned by Audacy, wanted to refresh its morning lineup. Hill was chosen to replace the long-running “Kirk and Callahan” show. His move marked a shift from rock radio to sports talk. The change allowed him to focus more on Boston sports and engage a wider local audience. His experience with live radio made the transition smooth. Hill quickly adjusted to the sports-first format. His presence helped stabilize the morning time slot during a period of change at the station.

Inside The Greg Hill Show: Format, Co-Hosts, and Listener Base

“The Greg Hill Show” airs weekdays from 6 a.m. to 10 a.m. It covers sports, current news, entertainment, and listener interactions. The program mixes analysis with humor, keeping a casual but focused tone.

Main elements of the show include:

• Time slot: 6:00 a.m. to 10:00 a.m. ET
  
• Co-hosts:
  
  • Jermaine Wiggins (former NFL player)
    
  • Courtney Cox (news updates and trending topics)
    
  • Chris Curtis (executive producer and contributor)
    
• Format: Sports discussion, interviews, local news, and audience call-ins
  
• Topics covered: Patriots, Red Sox, Bruins, Celtics, national sports, social issues
  

The listener base includes adults aged 25 to 54, mainly from Boston and surrounding towns. Many are long-time sports fans who prefer a balance of serious talk and light segments.

Greg Hill’s Influence on WEEI Ratings and Boston Sports Media

Greg Hill brought stability and fresh energy to WEEI’s morning block. After years of change in the early morning slot, his leadership helped rebuild trust with listeners. Ratings began to improve slowly after his arrival. The station maintained its presence as one of the key voices in Boston sports radio.

His impact can be seen in these key areas:

Area	Impact Since 2019
Morning slot ratings	Stabilized with slight growth
Listener engagement	Improved through digital polls and call-ins
Show consistency	Minimal staff turnover
Public recognition	Positive media coverage, especially post-2023 extension

Hill’s tone fits the Boston audience. He speaks directly, stays close to local teams, and reacts quickly to sports news. His long experience in Massachusetts radio makes him a strong match for WEEI’s goals.

Contract and Salary Insights

Greg Hill’s work at WEEI is backed by a multi-year contract. The deal shows his value to the station and its audience. While exact numbers are not public, some details are available. Industry sources help explain what he likely earns and how his deal is structured.

What Are the Terms of Greg Hill’s 2023 WEEI Contract Extension?

In late 2023, Greg Hill signed a new multi-year contract extension with WEEI. The announcement was made by Audacy, the parent company of the station. The exact number of years was not shared publicly, but the term “multi-year” generally refers to a minimum of two or more years. The deal confirmed Hill’s continued role as the lead host of WEEI’s morning show. The extension reflected WEEI’s intent to keep their lineup stable and their commitment to maintaining listener loyalty in the competitive Boston radio market. Hill’s leadership and consistency were major reasons behind the new agreement.

How Much Does Greg Hill Earn from WEEI?

The full financial terms of Greg Hill’s contract are not public. However, several industry sources have estimated his salary based on comparable radio personalities in similar markets. As a high-profile morning show host in Boston, Hill likely earns a six-figure salary. Most estimates place his annual income between $500,000 and $900,000. This range is in line with the value placed on top talent in major cities, where morning slots attract high listenership and advertising revenue.

Host	Market	Estimated Salary
Greg Hill	Boston, MA	$500,000 – $900,000
Comparable Host (Boston FM)	Boston, MA	$400,000 – $800,000
Comparable Host (NYC)	New York, NY	$600,000 – $1,200,000

These figures are based on radio analyst reports and media salary benchmarks.

Does His Deal Include Bonuses or Incentives?

There are no confirmed details about bonuses or performance-based incentives in Greg Hill’s WEEI contract. However, such arrangements are common in radio agreements at this level. Bonuses may be linked to audience growth, advertiser engagement, or show ratings. In many cases, top hosts receive added compensation if they hit specific performance goals. Hill’s contract may include similar features, especially given the importance of his role in maintaining the station’s ratings. While no exact numbers are available, industry practice suggests that incentives are likely part of the full agreement.

Greg Hill’s Sports Coverage on WEEI Radio

Hill’s show talks about sports every day, but not just scores. He discusses trades, coaching choices, and what fans really care about. His focus is always on the teams that matter most to Boston.

What Sports Does Greg Hill Primarily Cover?

Greg Hill focuses mainly on professional sports teams based in Boston. His daily show gives strong attention to the NFL, MLB, NBA, and NHL. Most of the discussions center on the New England Patriots, Boston Red Sox, Boston Celtics, and Boston Bruins. These teams form the core of local sports interest. Hill follows team news, game outcomes, player updates, and league developments. His coverage includes both in-season stories and off-season events like trades and drafts. He also talks about college sports occasionally but keeps the focus on Boston’s pro teams.

Red Sox, Patriots, and Boston Sports Talk Highlights

Greg Hill delivers daily updates and opinions on the Red Sox and Patriots. His show breaks down each game, covers key player performances, and discusses future matchups. Hill and his co-hosts often debate strategies, coaching decisions, and roster changes.

Key coverage points include:

• New England Patriots
  
  • Coaching changes and quarterback news
    
  • Game reviews and playoff chances
    
  • Free agency and draft picks
    
• Boston Red Sox
  
  • Weekly performance updates
    
  • Player injuries and trades
    
  • Division standings and playoff outlook
    
• General Boston Sports
  
  • Celtics and Bruins updates when in season
    
  • Fan opinions through call-ins and polls
    
  • Reactions to national sports headlines
    

This mix of local focus and national relevance keeps the content fresh and engaging.

Notable Interviews and On-Air Moments

Greg Hill’s show has featured many interviews with famous sports personalities. These include past and present players, coaches, and analysts. He has spoken with Tom Brady, Rob Gronkowski, and other former Patriots about their careers and big games. He also brings in Red Sox players and front office staff for insight.

Some of the most memorable moments include:

• Live interview with Tom Brady during a Super Bowl week
  
• Charity Radiothon shows, where athletes join to raise money
  
• Immediate reactions to breaking news, like trades or firings
  
• Special guest appearances from local Boston sports legends
  

These segments often bring extra energy to the program and connect fans directly with the voices they respect.

Collaborations and Industry Presence

Greg Hill’s career has grown through strong partnerships on and off the air. He works closely with his co-hosts, producers, and many well-known names in Boston media. These collaborations help his show stay fresh, informed, and connected to the sports world his listeners care about.

Meet Greg Hill’s On-Air Team: Jermaine Wiggins, Courtney Cox, Chris Curtis

Greg Hill leads a team that brings different perspectives and energy to the WEEI morning show. Each member has a clear role and adds value to the broadcast.

• Jermaine Wiggins: A former NFL tight end who played for the Patriots. He provides football insight, especially on player mindset and locker room culture.
  
• Courtney Cox: Handles trending topics, pop culture news, and social updates. She adds balance with a lighter tone and often speaks on community stories.
  
• Chris Curtis: Executive producer of the show. He manages the content flow, brings in breaking news, and occasionally shares commentary.
  

Together, the team keeps the show dynamic. Their chemistry helps create a mix of sports analysis, humor, and news that appeals to a wide local audience.

Collaborations with Boston Media Figures and Guests

Greg Hill regularly works with other well-known media names in Boston. He invites journalists, broadcasters, and former athletes to appear on the show. These guests offer opinions, context, and behind-the-scenes stories that keep content fresh and informed.

Notable collaborators include:

• Bob Lobel: Former WBZ-TV sports anchor who joins for special features.
  
• Bob Ryan: Veteran Boston Globe sportswriter who adds expert analysis.
  
• Tom E. Curran: NFL reporter with deep coverage of the Patriots.
  
• Michael Felger: A sports radio host sometimes featured in crossover events.
  

These relationships expand the show’s reach and help maintain its authority in local sports coverage.

Appearances on Local TV and Digital Media

Greg Hill has also made appearances on Boston-area television. He has been a guest on NBC Sports Boston, sharing views on Patriots games and other local sports topics. His interviews are often replayed across digital platforms, including YouTube and podcast networks. While his main focus is radio, these appearances give him exposure to audiences who follow sports news online or through cable channels.

He also engages with fans through digital segments and WEEI’s social media accounts. Short video clips from the morning show are posted regularly, helping the station reach viewers beyond live radio hours. These efforts reflect Hill’s awareness of media trends and the growing importance of digital access.

Digital Expansion

Greg Hill reaches more than just radio listeners. His show is available across streaming apps, social platforms, and podcast services. These digital tools help him engage with fans who prefer on-demand content. Whether through full episodes or short clips, his voice is now part of multiple formats beyond the studio.

How Greg Hill Reaches Audiences Beyond Traditional Radio

Greg Hill understands that many people no longer listen to radio in the same way. To stay connected with more listeners, he and his team expanded into digital formats. His morning show is not limited to FM radio. It is also available through live streaming and on-demand audio. This gives fans more ways to listen during the day, even if they miss the live show.

WEEI’s website and mobile app feature full episodes and highlight clips. Hill also uses WEEI’s digital tools to share polls, answer questions, and collect feedback. These options let the show reach both local and out-of-state listeners who care about Boston sports.

Use of Podcasts, Social Media, and Streaming Platforms

Greg Hill’s team actively shares content across digital platforms. Full show recordings and short clips are available as podcasts. These can be played on services like Apple Podcasts, Spotify, and Audacy’s own platform. The podcast format gives users flexibility. They can choose what segments to hear and when.

The show also uses social media to boost engagement. Key channels include:

• Twitter (X): For real-time news, quotes, and show updates
  
• Instagram: For photos, behind-the-scenes content, and short videos
  
• YouTube: For longer video segments, interviews, and show highlights
  
• Facebook: For audience discussions and local news sharing
  

In addition, WEEI has experimented with Twitch and other video streaming sites. These platforms allow fans to watch the hosts live in the studio. That visual connection builds stronger loyalty and helps reach younger users who prefer video content over radio.

Together, these tools make Hill’s show accessible to a wider, more digital-savvy audience.

Greg Hill’s Business Ventures and Side Projects

Greg Hill has expanded his career beyond radio through local business ventures. He owns shares in hospitality projects and runs a nonprofit foundation that supports families in crisis. These efforts show how he balances media work with entrepreneurship and community service.

Greg Hill’s Investments in Restaurants and Hospitality

Greg Hill is involved in the restaurant and hospitality business in the Boston area. Over the years, he has partnered with several local businesses and invested in dining and nightlife venues. These projects add to his income and connect him with the local economy outside of radio.

His business interests include:

• Howl at the Moon Boston: A live music bar where Hill has been a partner
  
• Battle Road Brewing Company: A brewery and restaurant operation located in Maynard, Massachusetts
  
• Other restaurant ventures: Smaller partnerships in food and beverage locations around Greater Boston
  

Hill uses his local profile to support these businesses through promotion and community engagement. His work in hospitality reflects his focus on creating spaces where people can gather and connect.

The Greg Hill Foundation and Its Impact

Greg Hill started The Greg Hill Foundation in 2010. The goal of the foundation is to provide financial support to local families and individuals after unexpected tragedies. It is a non-profit group based in Massachusetts and is known for its quick-response donations.

Impact by the numbers (as of 2024):

Category	Total Impact
Total money donated	Over $27 million
Number of families helped	More than 9,000
Main event support	Road races, radiothons, concerts
Corporate and local partners	Dozens of New England businesses

The foundation works closely with the local community and responds within days to major events. It has helped families after house fires, medical emergencies, and other personal losses. Many of WEEI’s charity events also raise funds for the foundation, making it an active part of Hill’s public life and mission.

Greg Hill’s Net Worth Overview

Greg Hill’s finances reflect years of steady work. His income comes from radio, business, and side projects. His earnings come from multiple sources, including radio, hospitality, and digital platforms.

What Is Greg Hill’s Estimated Net Worth in 2025?

Greg Hill has an estimated net worth of $10 million in 2025. This figure reflects earnings from his long-running radio career, business ventures in the hospitality industry, and consistent revenue from digital media and live events. 

His role as a morning host on WEEI, combined with equity in restaurants like Battle Road Brewing Company and Howl at the Moon Boston, contributes significantly to his overall financial standing. Public data from industry sources confirms this valuation, which places him among the top-earning regional radio personalities in the U.S.

Income Sources Beyond Broadcasting

Greg Hill earns money from several sources. Although WEEI remains his primary income stream, his business and public roles also contribute.

Breakdown of his known income sources:

• WEEI Morning Show Host: Main salary estimated at $500,000–$900,000 annually
  
• Restaurant Partnerships: Profit shares from hospitality investments in Greater Boston
  
• Digital Content: Podcast platforms and streaming shows generate modest ad revenue
  
• Event Hosting: Paid appearances and charity-related public speaking
  
• Sponsorships: Local business tie-ins through on-air promotions and brand partnerships
  

This mix of steady and flexible earnings helps keep Hill’s financial profile stable and growing.

Properties, Assets, and Financial Footprint

Greg Hill owns property near Boston, where he currently lives with his family. His home is located in Framingham, Massachusetts. It is close to WEEI’s studio and other business locations. He also holds investment shares in food and drink businesses across the state. While there are no public records of luxury assets, Hill is believed to own multiple vehicles and manage private savings accounts tied to his long career.

Summary of key assets:

Asset Type	Description
Real estate	Home in Framingham, MA
Business holdings	Shares in restaurants and breweries
Vehicles	Several personal-use cars
Bank/investment funds	Private financial accounts

His overall financial approach appears practical, with a focus on stable growth and community involvement.

Greg Hill’s Awards and Recognition in Broadcasting

Greg Hill’s career success is not only measured by ratings but also by the recognition he has earned from the broadcasting industry and local community. Over the years, he has received awards that highlight both his talent on-air and his impact off the microphone.

Awards and Honors in Broadcasting

Greg Hill has received recognition for his long-standing contributions to radio. One of his most notable honors is the 2022 Marconi Award, which celebrates excellence in broadcasting. This award is given by the National Association of Broadcasters and is one of the highest achievements in the U.S. radio industry. Hill was recognized for his leadership, audience connection, and consistent performance on-air.

In addition to national honors, Hill has also been acknowledged locally by Massachusetts media groups and charities. These awards reflect not just his professional skills but also his positive influence on community life through media.

Key awards and honors:

Year	Award	Reason for Recognition
2022	NAB Marconi Award	Excellence in radio hosting
2020	WEEI Listener Recognition	Most Trusted Local Host (internal vote)
Ongoing	Local Community Awards	Contributions to charity and public work

These awards help confirm Hill’s role as a respected voice in Boston broadcasting.

Philanthropy and Local Impact in Massachusetts

Greg Hill is active in charitable efforts across Massachusetts. Through The Greg Hill Foundation, he supports local families facing sudden emergencies. The foundation offers fast financial relief and has become a trusted name in the region. Hill also helps organize fundraising events such as charity runs and radiothons.

Outside the foundation, Hill regularly partners with schools, fire departments, and health causes. His radio show often highlights nonprofit groups and encourages public support.

Key community impacts:

• $27 million+ raised by The Greg Hill Foundation
  
• 9,000+ individuals supported since 2010
  
• Annual charity events run with help from local businesses
  
• Radio airtime dedicated to local crisis response and awareness
  

His continued focus on giving back has made him not only a broadcaster but also a well-known figure in civic life.