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Mark Kenney - retirement

In today’s world, we tend to throw the words legend and legendary around as casually as we might with a baseball in our backyard. This is not one of those days.

We couldn’t be more thrilled to share this episode with an absolute legend and icon in Boston Sports radio, TV, media, and film, Mr. John Dennis. John’s career in the Boston sports world started in the 1970s and continued into the 90s and 2000s with the Dennis and Callahan morning radio show.

He’s won several Emmys and other broadcasting awards in his storied career with WEEI, with roles as weekend and weekday sports anchor, producer, and director. He’s also made a huge impact with his charitable work with the Jimmy Fund, the Cystic Fibrosis Foundation, and on the board of directors of the Mutual Funds Against Cancer Organization.

If sports has been a big part of your life over the past 50+ years, even if you haven’t lived in the Boston area, John’s voice is likely a familiar one. He’s interviewed legendary sports figures and been on the scene (and behind the scenes!) to cover some of the most memorable moments in sports history. Anyone who has been able to have access to Tom Brady and Bill Belichick on the Patriots Monday radio call every single week-win, lose or draw-during their tremendous run undoubtedly has achieved legendary status with some epic stories to tell.

In this conversation, we go back to the beginning of his career as he paints a picture with great detail of what some of the most memorable moments in sports looked like from his seat. From the great Celtics runs in the 70s and 80s, golfing with the greats, his cameos in the Farrelly Brothers’ movies, being on the air during the tragedy on 9/11, and how he overcame his battle with alcoholism. As they say, he’s been there and done that, and we’re thankful to have him with us today.

Even if you’re not a sports fan, there’s a little something for everyone. There’s a backstory to every big story, and they’re being brought to you today by one of the greatest voices in Boston Sports, John Dennis.

In this podcast discussion, you’ll learn: 

  • How Derek and John met and the role that golf has played in their friendship.
  • The lesson that John learned from his father and how John discovered his love for sports broadcasting.
  • How John’s work ethic and passion was a huge factor in leaving Kansas City to work in Boston.
  • How John was able to have incredible access to boxing legend Marvin Hagler.
  • Some behind the scenes moments from the most amazing prize fight at the time, Hagler vs Hearns.
  • How he met John Havlicek and how his access to the Celtics teams grew over the years.
  • Stories of Larry Bird that you won’t want to miss.
  • What it was like behind the scenes of the 1986 World Series with the Red Sox and Mets and the events that took place after the Bill Buckner play.
  • The incredible memories of golfing with Lee Trevino and Greg Norman.
  • What it was like to be on the air during the tragedy on 9/11.
  • How Patriots Monday came to be and how his access to Tom Brady led to their friendship.
  • The incredible moment when John reached out to Tom Brady after learning that his good friend and Patriots Superfan was near the end of his battle with ALS.
  • How John was a highly functioning alcoholic and the moment that he knew he had to get help.
  • How he became friends with the Farrelly brothers and how he landed his role in Kingpin.

Inspiring Quotes

  • Find something you like to do versus something you have to do. And if you hate doing what you’re doing for a living, that would be a lifetime sentence of 45 years. That’s like going to prison for 45 years.” – John Dennis
  • “You can give up everything in your life for just one thing or you can give up just one thing in your life and have everything.” – John Dennis

Interview Resources

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[INTRODUCTION]

 

Derek Gregoire: How you doing? I’m Derek Gregoire. And today on the Retirement Roadmap, we’re joined by radio and TV broadcasting legend, John Dennis. In 1977, John joined Channel 7 in Boston and spent 20 years covering Boston Sports as an anchor, producer, and a director. During his time on television, John won many awards, including multiple Emmys and the Associate Press Best Sports Coverage Award in 1983 and ‘84. In 1997, John joined forces with Gerry Callahan on the Dennis and Callahan Show on WEEI. As a number-one rated show among male listeners between 25 and 54, Dennis and Callahan hosted the morning show until 2016. During their time on air, the Patriots, Bruins, Celtics, and Red Sox all won championships. John has been involved with many Boston-based charities throughout his career, raising money for the Jimmy Fund, the Cystic Fibrosis Foundation, and he is on the board of directors for the Mutual Funds Against Cancer Organization.

 

He’s also been featured in multiple movies, including Kingpin, Me, Myself, and Irene, Shallow Hal, and Stuck On You. And throughout this episode, we’re going to hear some amazing stories of just John’s career, the behind-the-scenes stories of whether it’s Johnny Amos, Larry Bird, a lot of cool golfing stories, Tom Brady, a text message he had Tom Brady send his friend when his friend was going through a terrible illness. We’re going to hear stories of some of his movies he’s played and how that came about and him hanging out with Bill Murray. Make sure you tune in at the end because we will actually be talking about his struggle with addiction and how he was able to overcome that and really an update on what’s going on in John’s life now.

 

So, without further ado, John Dennis.

 

Show Transcript

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