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



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.




Derek Gregoire: Over the last several weeks and years, I would say we’ve brought a ton of different topics around I’d say the boring but important financial planning, debt ceiling, interest rates, mortgage rates, market, stocks, bonds. But we’re going to go in a different direction today. We’re lucky enough to be joined by what many of our listeners and clients and myself know as for all of our Boston sports fans a local legend here and a good friend of mine who’s down in Florida, John Dennis. Welcome to the podcast.


John Dennis: Derek, good morning. How are you doing?


Derek Gregoire: I am doing great. For the people that are watching this through our Zoom, I think they can tell that you’re probably doing better than me based on the view behind you.


John Dennis: Well, I’m doing okay. It beats working in a steel mill, which is what I used to do in high school and college. So, this is better.


Derek Gregoire: That looks a little bit better these days. So, backtracking a little bit, how we met, I think may be a good starting point. We have a mutual friend who, if we can find a way to roast him on this show, that would be great.


John Dennis: You mean Mikey?


Derek Gregoire: Good old Mikey. Yeah. That’s easy to do. I don’t know if we can do it in a PG-13 way but we’ll find a way to get those outbound sticks legs made fun of.


John Dennis: Okay.


Derek Gregoire: So, Mike’s a good friend of both of ours. Mike he lives in the same area in Massachusetts as my wife and I, him and his family. He bought a place in Florida, and it happened to be the same place where John and Cathy owned a home. So, they hit it off. We played some golf up here at LeBaron, and over the years, the funny story is my wife, Kathleen, has always wanted a place in Florida for us to go to visit, to have children, school vacations, a place to sneak off to for my parents and her parents to kind of sneak down to in the winter. And all these years I’ve been like, “Yeah, we’ll do at some point.” And then she goes, “All of a sudden you have two friends that have a place down there and now you’re ready to look.”


John Dennis: And the fact is we did all the research for you. You didn’t have to decide whether you wanted the Atlantic Coast or the Gulf Coast. You didn’t have to decide whether you wanted bundled golf or no golf course. We did all the work for you and then you just jumped in at the end and took advantage of what Mike and I did before you got here.


Derek Gregoire: And I even had your wife, Kathy, to help us. She showed us like all different properties all across the area, and we fell in love with this place in Venice. And so, myself and John and Mike all live in the same community. We golf a lot together. We watched Super Bowls together and have dinners. We’ve got a lot of fun over the years and I’ve been growing up. I don’t know if you knew this, John. When I was in high school, my number one dream was to become a professional athlete. And I love baseball, but football with my sport I really wanted to do but when you realize you’re 6 foot, maybe stretching to 6’1, 210 pounds as a tight end, there’s not many opportunities in the NFL. So, that brought me I really wanted to do broadcast like I love sports radio. I was like if I can talk sports all day, that would be an amazing way to go through life. And I had actually years ago visited your show, The Dennis and Callahan Show. I had a friend of a friend who was the producer of your show, and we went for the day.


If I had known how to get into the broadcasting industry, I would have definitely loved to have gone down that road. I’m happy where I am now, but I love sports. I love talking sports. So, before we go back in time, let’s let everyone know how John Dennis is doing now. What are you up to now? What’s going on?


John Dennis: Well, I play golf but only on days that end in Y. I spend about eight and a half months here in Venice, Florida, and the other three and a half or four back up in Boston. So, I stay here through about the 4th of July and I come back down around Halloween, something like that. I got sober in 2014, kind of straightened my life out, decided I wanted to live beyond 65 or 70. So, that’s my goal now. My doctor tells me he can get me to 100. I’m not sure I would make it to 100, depending on what I’m shooting at that point on the golf course but that’s the plan so far.


Derek Gregoire: That’s awesome. Yeah. Look, I know firsthand you’ve been doing great. And funny story, we moved in. We bought the place. Our place wasn’t really done yet. And so, we had asked John and Kathy if we could order some stuff because it was during COVID and we wanted to order some like couches and get things ahead of time and say, “Hey, do you mind if we store a couple of items in your garage?” “Oh, no problem. No problem.” Well, I get a text a month later. “Hey, Derek, do you know any place that rents out spots for our cars that we can park? Because we have nothing left in the garage. There’s no space left in the garage.”


John Dennis: You still haven’t sent the money for the bill that I sent you for the storage.


Derek Gregoire: I know but I try to give an occasional financial planning tip every once in a while to try to chip away at the debt.


John Dennis: Okay. We’ll call it even.


Derek Gregoire: So, going backwards, there are so many cool stories I want to get into that I loved hearing all these stories. And as a Boston sports fan, I know everyone’s going to love hearing some of the behind-the-scenes action and things that you get to partake in over the years. But just going back to when you were younger, I believe you grew up in Pennsylvania. Besides your voice, which basically you were destined for this type of career, but when did you know or how did you get into television and radio?


John Dennis: Well, it was a result of the aforementioned steel mill situation. My dad made me work in the steel mill every summer, starting after my ninth-grade year. And I’m not sure how I got in under the age limit, but I was younger than I should have been. And every summer after my 9th, 10th, 11th, and senior year in high school, and then in the summers after my freshman, junior, sophomore, and even senior year in college, as soon as school was over, I was in the Pittsburgh steel mill and I really, really resented my father for making me do that as I’m watching all my pals head to the beach or go to the pool or play golf all summer long. And it was such a difficult thing to do for three months every summer that I literally really looked forward to September and going back to school. And as I said, I resented my father for making me do it.


And then it kind of dawned on me what he was doing. He was giving me an object lesson as to 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. I mean, that’s like going to prison for 45 years. So, it was an object lesson that played out over seven or eight years. It made it very clear to me that I wanted to find something that I like to do that I love to do, it was fun to do, and I wouldn’t mind doing it for 40 or 45 years. So, early on I kind of thought broadcasting would be it. I like sports, I like broadcasting. So, even in high school, I was announcing the morning announcements over the loudspeaker. I was the emcee for the band of the chorus concerts at Christmas. I didn’t play football in high school but I did the announcements over the loudspeaker. So, one thing led to another, and by the time I got my junior, senior year, I started looking for schools that majored in this that would have good programs in this. I looked at a number of them and settled on Kent State in Ohio. They had tremendous program. Telecommunications, it’s called.


And they have a radio station, two radio stations, AM and FM, and a TV station that is not just in-house but is part of the Kent, Ravenna, those are the communities around Kent State, broadcast out on cable. So, every night at Kent State, they are responsible for providing three or four hours of live real-time programming to the communities of Kent State. It’s not a laboratory situation where if you mess up, you can stop and start tape again and begin again. We were alive four hours a night. So, with that amount of experience and I started working at the radio station my freshman year, and the reason I was able to do that is nobody wanted to do the sign-on shifts Saturday and Sunday morning because generally when you’re in college, you’re hungover Saturday and Sunday morning. So, I volunteered and said, “I’ll do it,” and went up and make coffee and rip the wire and wrote copy and news, and all that sort of stuff. So, that’s sort of how I get started.


Derek Gregoire: So, you didn’t have any fear of even like in high school, public speaking, or being in front of people.


John Dennis: No. I’m too stupid to have fear.


Derek Gregoire: Now, I don’t know about that. It’s funny. I’m not going to go down this road, but I probably share with you but my dad had a similar story where it was a summer where I wasn’t working and I was probably 14 and he’s like, “You better get a job. You better get a job.” And I kept saying, “Oh, I’ll get one eventually.” Well, two weeks later, he woke me up at five in the morning, 95 degrees, humidity, brought me down to a field where he’s like, “I’ll pick you up at 7:00 tonight and you’re going to be baling hay with these guys for the entire day.” And so, 7:00, he picks me up, I’m drenched, sore, cut up, just a mess. He goes, “You’re ready to come back tomorrow?” I said, “I’ll find something else to do. I promise I’ll find a job.” And I found a job right away and then I plastered with him. He was a plasterer. And he always wanted me to try to go to college.


So, eventually, one of those days, I had that point where I was like, “Hey, Dad, do you mind if I go to college?” And he’s like, “What do you want to do?” I was like, “Anything but this.” A lot of times those lessons in this day and age you hope I feel like every generation, my generation, and my kids have it much better than I did, and I had it much better than my parents. Hopefully, I can keep that going with my kids. It’s just tough these days, you know? It’s just tough.


John Dennis: It is different. I don’t want to sound like, hey, back in my day, we used to do it this way and I’m going to be shaking my fist to clouds and telling kids to get off my lawn. But I think the fact is that your dad and my dad in a certain way knew that they don’t want to hand us anything. They want us to understand the value of a dollar, the value of working. Now, and again, I hate to sound like this old man. It’s a hands-up, palms-up society, you know? What can you do for me? What can you give me for free? Can I get a participation trophy just for showing up? And I know you’re aware of that, and I’m certainly aware of it with my kids, and they turned out well, and I’m pretty sure yours are going to as well. But it’s that idea of something for nothing. I don’t want to go back to work now that COVID’s over. I want to work three days at home or whatever the case may be. I think it’s just a kind of a different mindset we somehow have in this country that wasn’t that way when certainly when I was younger and probably not when you were either.


Derek Gregoire: No, you’re right. And so many of our clients like it’s amazing how many out of the client’s financial plans over the years that have had the most trouble, I would say, are the ones that didn’t work for it. So, I’ve had some clients that hit the lottery and done fine, but I’ve had some that hit the lottery and literally gone through money faster than you can imagine. I’ve had clients inherit millions and gone through it, but a lot of our core clients, they kind of like grinded it out, worked their butts off, put their kids to school, did as much as they could for themselves, the next generation, to give themselves a chance at retirement and they’re much more disciplined. They can handle the pressures and the budgets and the things they have to stick to because they’ve been through it. And hopefully, I can instill that on my children. You always worry because I sound like an old man now talking about like just I see the youth in their eagerness to work and want to get dirty. And it’s like, man, I have to go 8 hours to one job and think that’s a long time, you know.


John Dennis: A friend of mine that I was golfing with last week told me his brother teaches a vocational class somewhere I think in Ohio. And he had nine kids in the class that were seniors and he helped place all nine of them in jobs. And within two months, he had gotten calls back from eight of the employees and said no good. As soon as I give them an assignment, the second they finish it, they sit down and get on their phone. They’re not self-starters. They don’t say, “What can I do next?” They don’t worry about the quality of the work that they have just because everything has been handed to them. So, again, I know we sound like old men shaking our fists to clouds but that’s the way the world these days.


Derek Gregoire: That’s the reality. I know we can go down this rabbit… I’ll probably stay away from this rabbit hole for us because we can go down this rabbit hole for a while. So, you left Kent State. I know you started in TV, right? What brought you to Boston?


John Dennis: Well, I was very fortunate. I was one of the last finalists for ABC’s coverage of college football in 1974. They had a nationwide search looking for a college-age announcer. Now, keep in mind, this is ‘74, my senior year in college, and I had already had 500 or 600 hours of broadcast experience on WKSU, the TV channel and the radio station. And I read an article that Roone Arledge from ABC Sports was looking to hire something new and innovative, a young college-age announcer to roam the sidelines during football coverage, ABC’s football coverage of college football. And so, I’m like, “This got my name written all over it.” So, I write Roone Arledge a letter, and I sent it away. And about three weeks later, I get a phone call from Dick Ebersol. I don’t know if you know that name but he’s a big name in sports now. And Ebersol says, “Hey, we’ve got your resume. We’ve got your letter. We’d like to meet with you and interview you.” And I said, “Fine. Where?” And they said, “Well, Ohio State. You have to go to Ohio State. We’ll meet you in such and such a time on this date in this room.”


So, my then girlfriend, later my wife, now my ex-wife, and I got in the car from Kent State. We drove to Columbus, Ohio, and we look up the, you know, we find the building, we walk in. There are 900 people in the auditorium. 900. I come to find out that that was one of eight different collegiate centers that they were interviewing between 700 and 900 people. And there was one at UCLA. There was one somewhere in Arizona. I think they had one up in Michigan. They had one is Penn State, a couple in Florida, a couple in Midwest. So, they were looking at 8,000 people to interview, and I’m not sure how they winnowed it down. And I said, “Wow, I thought I was coming here to Columbus, Ohio, to sign a contract and get the job.” And I realized I got no shot here. About a month later, I finally get a phone call and they said, “We have narrowed it down from a thousand people to 500, now down to 100. And we’ll get back in touch with you, but you’re in the final 100.” All right.


So, I waited a little bit longer and I got a call, I don’t know, a few weeks later and said, “We’re down to five. You’re in the final five and we’re going to bring you to New York.” They took us to New York, we met with Roone Arledge. So, they picked our brain. They said, “If you got this job, what would you do?” And I gave him all these ideas that I would interview, get all this so-and-so, so-and-so forth. And we met with Roone Arledge, and it was like walking into the Wizard of Oz office. It’s overlooking Manhattan. He had floor-to-ceiling shelves with Emmy Awards all over the place, and he’s sitting up high. So, like, he’s in the positive position looking down on you and he talked to us and the producer of the football telecast talked to us. They picked our brains and eventually, I did not get the job. Jim Lampley, I don’t know if you know that name.


Derek Gregoire: Oh, yeah. Yes.


John Dennis: Ended up getting the job and I did not. But as a result, I was able to put that experience on my resume. So, when I graduated, I sent it out to about 200 different TV stations across the country and said, “Penn State University, Telecommunications major, 500 or 600 hours of on-air experience. Here’s my resume. And oh, by the way, I was one of the five finalists for ABC’s college-age football announcing job.” And I sent out 205 resumes. I got 204 nos. In fact, one guy from Seattle said, Seattle of all places, writes back and said, “How dare you waste my time thinking you can come out of college and come to Seattle and get on the air.” And I thought to myself, “Wouldn’t a simple yes, I mean, simple no have been easier to do?” And one guy whose name is Ken Keller was the News Director at the NBC affiliate in Kansas City wrote back and said, “Impressive resume. We don’t have anything right now, but please stay in touch.” Well, that was his big mistake. He said, “Please stay in touch.”


I called him every Monday afternoon at 2:00 mid-afternoon and said, “Hi, Mr. Keller, John Dennis calling from,” where was I? I was in Pennsylvania at that time. And I just bothered him and bothered him and badgered him and badgered him. And finally, only because not I was good but he was sick of hearing from me. He said, “All right. I’m going to fly you out for an audition and see what happens.” And they flew me out and they gave me the job and I became the youngest sports director at age 22 in the history of NBC affiliates, which sounds like a good thing, but I didn’t know anything. I was wet behind the ears. You heard the expression, fake it until you make it? That’s what I did. But the good thing was Kansas City at that point had all four major league sports. They had, of course, the Kansas City Chiefs, the Kansas City Royals. They had the Kansas City Kings basketball team, which is now in Sacramento. They had the Kansas City Scouts, which eventually went, I think, to Colorado.


So, the point of telling you all that is that all four major sports were available for me to cover. And the best thing about it was people in Kansas City aren’t like sports fans in Boston. They’re very forgiving. If you say something stupid or you say something wrong, they don’t cut your head off. In Boston, if I said some of the things I said in Kansas City, erroneously in Boston, my career might have been over right away. They’re very forgiving in Kansas City. And so, I did three years there and I honed my skills and I got better at it. And then I started sending out a second wave of resumes and sent one to Boston and a guy named Dick Graf brought me out for an interview and an audition. And odd story there, on my way back home to Pennsylvania, I’m sitting in the lounge, the cocktail lounge at Logan Airport after having done the interview at the Government Center in Boston at Channel 7, and Ray Walston from My Favorite Martian is sitting next to me. And I had like this half-hour conversation with Ray Walston, My Favorite Martian. I told him all about why I was there and he’s very nice, man. So, that’s just an aside.


And I go back to Pennsylvania and I end up getting a job. So, that’s how I ended up in Boston. I came here at the end of 1977. So, keep in mind, my first winter in Boston was the blizzard of ‘78. And I looked at everybody and I said, “Are you kidding me? This happens every winter in Boston?” They said, “No, no, this is different.” I said, “Well, thank goodness because I can’t deal with this every single winter.”


Derek Gregoire: Well, no, it’s crazy, John, as I think if you can probably hear, I bet, like I remember when I was trying to get out of college and into the career, we started this company in ‘03, but to break into the career, I had that thought in the back of my head like you don’t want to go back to plastering, you don’t want to go back to plastering. And I think the way you hounded that producer and the person over in Kansas City, I bet you had your dad, you probably had a little bit of that steel mill in the back of your mind, like either one. So, you were just grinding to get that opening and get that start because if not, you might have to go back to something you don’t want to do.


John Dennis: Exactly.


Derek Gregoire: So, you started in was it Channel 7, right, in Boston?


John Dennis: Right.


Derek Gregoire: And how many years were you there for?


John Dennis: Twenty years there and then 20 years at WEEI for trading.


Derek Gregoire: Got it. So, that’s obviously my years. I was born in ‘79. Not to date anyone here. So, I don’t remember. I know a lot of our listeners and clients remember the Channel 7 days. And I guess my question from that, from going from Channel 7 to radio, wouldn’t that have been like and maybe I’m not reading, don’t remember what it was like back then, but wouldn’t have been like a risky move in a way where like Channel 7 space-time, you’re on the air. Everyone knows you by face then you’re going to radio behind the scenes. How did you make that transition?


John Dennis: Well, it sounds like it’s almost doing the same job but it’s really, really very different. Anchoring the 6:00 and 11:00 sports on television is not that hard of a thing to do. I mean, given enough bananas, I could train a chimpanzee to read the teleprompter in that three or four-minute window. And essentially it’s, “This team beat that team by this score and here’s a highlight. Okay. This team beat that team by the score. Here’s a highlight. And here is the schedule for tomorrow’s playoff situation. Goodnight, everybody. We’ll see you tomorrow.” I mean, there is no creativity to it. There is no difficulty to it if you learn how to read the teleprompter correctly. And it was just a sort of boring grind. And the other thing that was happening is as more entities became available for the listener or the viewer, such as SportsCenter or NESN, the time that the evening anchors, that would be Bob Lobel, Mike Lynch, and John Dennis got, the time that we got every single broadcast were shrinking every single year.


I remember when the 6:00 news, I’d have 6 or 7 minutes to do features and other things. 11:00 you have maybe 4 or 4.5 minutes. That began shrinking and shrinking and shrinking because there were other ways to get that information for people. And so, it ended up being just almost like a headline service. You know, that 2 minutes at 11:00 and 3 minutes at 6:00, I was kind of getting bored with it and tired of it and Jason Wolfe was the program director at WEEI.


Derek Gregoire: I know Jason.


John Dennis: He’s a good friend of mine and he got the idea for putting together a TV guy and a print guy, Gerry Callahan, who was first at the HeraldNet Sports Illustrated at that time and put the two of us together, and see what would happen. And it was a kind of a safe experiment because he didn’t give us anything prime time. We worked the midday from 10 to 12 and we replaced the Fabulous Sports Babe, which you probably never heard about. She just did a two-hour show and she was terrible, so we almost couldn’t fail. And it worked pretty well and they expanded us to morning drive time and we ended up doing 20 years from 6 in the morning until 10 every single day, which was great, except for the 3:45 wake-up call every single morning for 20 years. There were some mornings, Derek, that when the alarm rang, I just wanted to cry. I said, I can’t believe it’s 3:45 and I’ve got to get up and go to work. But that was the only downside to the whole project.


Derek Gregoire: Yeah. We’ve talked about that over the last couple of years, as you’ve said that many times, like just the day you come home, you go to bed, the alarm clock keeps going off and it’s like, “Oh, I can’t do this right now.”


John Dennis: Try doing it when you’re drinking, by the way.


Derek Gregoire: Yeah. That’s another story. We’re going to get into that in a little bit. So, over the years, obviously, I want to get to some of the stories now because there’s so many of them. When you started out in Channel 7, I know you had, and I didn’t know this until we get to know each other but you had a passion or you covered a lot of boxing. And was it anyone in particular that you covered mostly or was it just the whole?


John Dennis: It was Hagler-Centrum.


Derek Gregoire: Okay.


John Dennis: I mean, we were the first ones from Channel 7 to go down to Brockton in the Petronelli Brothers gym. And I’ve said this many times, I knew Marvin when he had hair. I actually have interviews on film and pictures of Marvin and I together when before he had shaved his head. And so, we were the very first ones in on Marvin before anybody else realized he was destined for stardom. I think the first fight I covered that he did was against somebody named Willie the Worm Monroe from Philadelphia. And he, of course, crushed him. And so, as a result of being first in, I became very good friends with Marvin and very good friends with Goody and Pat Petronelli. So, we always had the inside scoop as Marvin ascended up the ranks of the middleweight division. Who he was going to fight next and when he was going to fight next? And I would go to his training camp and give us all these exclusives. When we got to Caesars Palace for the big fights, Marvin would sit down with me and only me because of our history going back together. So, that’s sort of how it all began.


Derek Gregoire: That’s so cool. And then you had a story. I remember something about a referee or something around Hagler.


John Dennis: It was the, in fact, people ask me, what is the favorite sporting event you’ve ever covered in your life? And I’ve covered a lot, but without question, the Hagler-Hearns Fight, April 15, 1985 Caesars Palace was by far the most entertaining, most amazing, most, I don’t want to say life-changing, but eye-opening thing I’d ever seen in the world of sport. And it was this build-up of a couple of weeks. We went out to Las Vegas, stayed at Caesars Palace, did all the training stuff. And it was such a build-up and there was such animosity between Hearns and Hagler. And I’m sitting courtside. I’m sitting ringside, I should say. John Madden is on my right and Bob Neumeier, the late Bob Neumeier from Channel 4, sitting on my left. And we’re sitting there and watching the end of the preliminary, and they’re starting to do the introductions and they’re bringing them in. And Neumeier looks at me and says, “Are you nervous?” I said, “Yeah, I can’t believe it. I’m not even involved here and I’m nervous.”


And it was just an absolute Rock ‘Em Sock ‘Em Robot if you’ve seen the fight. And if you haven’t seen the fight, look it up on YouTube. It’s worth the three rounds. Won’t take you long. And it was amazing. Marvin punched Tommy in the face. Tommy punched Marvin in the face. Hagler punched Hearns three times in the face. Hearns punched Marvin three times in the face. I mean, back and forth. They went back and forth. And finally, I believe in the second round, a giant cut opened right between Marvin’s eyes. And blood is streaming down his face and he is wailing away at Hearns and Hearns is wailing back at him. And the blood’s pouring down Marvin’s face and Richard Steele stops the fight and takes Marvin over the corner and he brings the ring doctor in. Dr. Flip Homanksy was his name. And he wipes the blood off. He looked at the cut and Richard Steele, the referee, looks at Marvin and says, “Marvin, can you see?” And Marvin says, “I ain’t missing him, am I?” And Richard says, “No, you’re not missing him. Fight.” But Marvin knew that he had to get him out of there within the next round. And he certainly did that.


Derek Gregoire: He knocked Hearns out.


John Dennis: Oh, yes, he did. He knocked him out.


Derek Gregoire: Wow. I’m going to have to watch that fight. I know you’ve talked about it. I’ve never seen it, but I know people and I’ve heard people talk about it. I never actually have seen the fight.


John Dennis: The most amazing prize fight of all time. I can say that without fear of contradiction.


Derek Gregoire: That’s great. I don’t know the recall you have on these names and storytelling still amazes me to this day. Like, Flip Homansky, whatever this guy’s name is, the referee even.


John Dennis: If I can back up chronologically, my very first assignment when I got to Channel 7 in the fall of, I’m sorry, the spring of ’77, they assigned me to go to Philadelphia with the Celtics to cover the Celtics and the 76ers playoff round, and it was by far my biggest assignment at Channel 7 when I first got there.


Derek Gregoire: That was Dr. J. at that time, right?


John Dennis: Yeah. Billy Cunningham was the coach. Dr. J., Bobby Jones, Maurice Cheeks, and Billy the Micro. No. Billy was Detroit. Anyway, believe it or not, in those days, the Celtics flew commercial. There were not these charter planes they have now. They flew commercial and I got on a plane to go to Philadelphia for the game the next night and I’m sitting in an aisle seat in commercial and I feel this tap on my right-hand shoulder and a guy sitting one row back and across the aisle, I turn around and he puts his hand up. He goes, “Hi.” He says, “My name is John Havlicek,” and I resist the temptation to say, “No kidding.” He goes, “You’re the new guy at Channel 7, right?” I said, “Yeah. So, John Dennis.” He said, “Well, I’m John Havlicek. Nice to meet you.” He said, “Good luck,” and he said, “If you need anything in Philadelphia, give me a shout.” And I was scared to death to do this assignment. I’d never gone on the road before. I’d never covered an NBA playoff game before.


And of course, as soon as the game was over and I think they won by 2, walk into the locker room and immediately go to Havlicek’s locker to do the interview and he was very, very nice to me. So, it was something and I talk to John about this, God bless his soul, many times in the past, and he remembers that. But that speaks to the kind of guy he was that he would actually introduce himself and try to make me feel more comfortable in my first big assignment.


Derek Gregoire: That’s awesome. I know my dad talks about Havlicek, Bobby Orr, those are two of his favorite players growing up. And I know you covering the Celtics, that was mostly, well, that was all at Channel 7 but were you on the road with them?


John Dennis: Yes. Yes, indeed.


Derek Gregoire: I know you had a couple of stories around Johnny Most. Any that you can share?


John Dennis: I’m going to try to keep this PG-13. I don’t know if you recall Johnny Most and what his voice sounded like and how loud.


Derek Gregoire: When I first started like following sports, I remember my dad being like, I’m like, “How is his voice like that?” And he said, “I think he smokes a lot of cigarettes.”


John Dennis: About four packs a day.


Derek Gregoire: That’s all I remember. And Larry Bird. Do you have a lot of interaction with him?


John Dennis: Oh, yeah, Larry was quite the trash talker but you never knew it then. He wasn’t like Kevin Garnett, who if you were sitting courtside, you could hear him screaming obscenities at the opponent. Larry was much more subtle. But my funny story was way before they transferred training facilities from Hellenic College, which was just a grungy little old gym, they had a scrimmage and they brought in referees to officiate the scrimmage. And on this one particular day where they’re watching the scrimmage and this had to be, well, McHale was there, so it had to be ‘81, ‘82. And they brought in two officials, a guy and this woman who was an official, and they start the scrimmage just like a regular game. And Larry gets the ball the very first play of the game, blows the whistle, traveling. He hands the ball to her. They get down the other side. Whoever Larry was guarding has the ball, ball on you, 33 on the arm. Larry looks at her. They go back the other way. Larry gets the ball. Charging. Larry’s had it at this point, has the ball under his arm, walks up into her face, and says, “Apparently, you don’t know who I am.”


Derek Gregoire: Oh, no.


John Dennis: And the whole place cracked up and that sort of kind of cut the tension. She kept the whistle kind of a little quieter after that because it was sort of Larry saying, “Don’t you know who I am?”


Derek Gregoire: Was he a good guy to cover? Was he pretty…


John Dennis: Yeah, he was. Well, I’ll tell you what. When he first got here, he was extraordinarily shy. I mean, painfully shy. And he hated to do interviews, and he hated the postgame obligations that a star of his magnitude had to do. But apparently, somebody pulled him aside and said, “Larry, here’s what we’re going to do. We’re going to make you available after every game for 5 minutes. You’ll sit on it.” They actually had a trainer’s table in the middle of the locker room in the old Boston Garden. And he would come out and he’d say, “Oh, you got 5 minutes.” And he’d sit down and we would talk to him for 5 minutes. And when the 5 minutes was up, he was gone. So, he kind of grew into that role of being the spokesperson for the Celtics but he did it very reluctantly early on.


Derek Gregoire: Yeah. No, I know. I’ve heard different stories. I was just curious. It sounds like he was reasonable, but it took him a while to break into that role. Switching to like going a little chronologically with the Celtics, where were you when Reggie Lewis passed away? Were you at WEEI?


John Dennis: I was at Channel 7. Yeah. That was a huge story. That dominated forever. And if you follow the story, then you know Dr. Gilbert Mudge who prior to Reggie passing, after he had passed out on the garden floor that night, did all kind of testing, so on and so forth. And he was the one doctor of all the doctors they looked at that said, “It’s a benign heart condition. And we’ve done this table test where we tip him over. We do all these various things,” and he gave Reggie Lewis the green light to return to play. Reggie went to Brandeis, had the heart attack, and end up dying. And so, lawsuits and all the stuff that happened after that. It was a really, really tragic story.


Derek Gregoire: So, I didn’t realize that. So, there were other doctors that said he can’t play?


John Dennis: All of them. And Reggie’s wife, I think, was sort of the motivating force behind looking for doctor after doctor after doctor until she found one who told her and Reggie what they wanted to hear.


Derek Gregoire: Oh, my gosh. Yeah. I didn’t realize that. I remember that story. So sad. And flipping the script to as we go kind of chronologically during your career and probably bounced around a little bit but one of the first memories I have of sports was I was with my dad. I was probably seven and it was the ‘86 World Series. And the only thing I remember seeing Wade Boggs crying on the…


John Dennis: In the dugout.


Derek Gregoire: And I have that memory of being seven years old and wondering, I’ve never seen someone cry in sports before and I didn’t realize, obviously, I learned about the Buckner situation and, man, what a crazy life Bill Buckner had as a result of that one thing. Were you involved in that? Were you?


John Dennis: Very much so. In fact, I was in charge of doing the live shots back to Boston from Shea Stadium and about the, I don’t know, eighth or ninth inning, I left the press box and went downstairs, and we had our cameras and the cables were all cabled right to the front door of the Red Sox locker room.


Derek Gregoire: Oh, yeah, because they’re ready to win the whole thing.


John Dennis: Ready to win the whole thing. Ready to win the whole thing. And this is huge, you know? It had been forever. They were going to finally break the curse. And so, I’m sitting there and my cameraman’s there and I’ve got the earpiece in my ear and I can hear the game and there’s a New York City policeman standing right next to the door, and he’s got a transistor radio. He’s listening to the game. And now I’m beginning to rehearse my opening monologue before I go into the locker room and talk to people. And I had this whole thing about it was beautifully written, I thought. “Sons have become fathers waiting for this day to happen,” you know, all this flowery stuff about the…


Derek Gregoire: You had everything built. You had the whole speech ready.


John Dennis: All ready to go, just like one minute monologue to set up the live shot. And one thing happens after another. There’s the wild pitch from Stanley. Ball goes through Buckner’s legs. I’m saying, “Oh, my goodness.” The first thing that happens is when the game is over, the locker room door is open and I look in the locker room. There’s this gigantic pallet of iced champagne sitting right in the middle. There’s Bob Costas and Mrs. Yaukey up on a podium, getting ready to do the postgame interview, congratulating her on finally winning the World championship, the World Series. They open the door. They help Mrs. Yawkey off the podium. I’m watching this. They help her off the podium. They lead her out by the arm. They’re looking at all the champagne that is like gigantically sitting in the middle of the locker room, the clubhouse. They don’t know what to do with it. They find a tarp. They throw a tarp over the champagne.


And just as Mrs. Yawkey leaves and the champagne is covered, the first guy walking up the runway toward the clubhouse was Dwight Evans. He looked like someone had killed his dog. He’s got his head down. They all came in. And now they’ve said to me, “One minute until you go live.”


Derek Gregoire: Oh, no.


John Dennis: Everything I’ve rehearsed is out the window, and now I’ve got to figure out how I say, “They’ve absolutely blown the biggest chance in the world,” and now got to go to Game 7 and so on and so forth. But that was so surreal to watch that all unfold.


Derek Gregoire: Everything was ready to go.


John Dennis: Just ready to go.


Derek Gregoire: Make the last out.


John Dennis: Yeah.


Derek Gregoire: That’s great. Yeah. Again, I don’t know if it was Game 6 or Game 7 when Wade Boggs was crying. It might have been Game 7 at that point.


John Dennis: Game 7 after they lost.


Derek Gregoire: Okay. And that was at Shea Stadium, too, right?


John Dennis: That’s right. It’s a big rain delay in between. After Game 6, I think there were two or three days they didn’t play. Then they played Game 7 and they lost.


Derek Gregoire: Got it. Yeah. I remember my dad being pretty upset with that one. That was like for me, the ’07 undefeated season of football when you get that far. But I do want to get into some Brady stuff because I find that fascinating, your relationship with Tom Brady over the years. But one thing that we both love to do is golf. And on the golf course with you many times I’ve heard a lot of cool golf stories on your side around different things. And from what I remember, you golf with a couple of legends over the years.


John Dennis: Well, here’s the story. I don’t know if you recall the PGA stop at Pleasant Valley for many years. It was called the Carling Open. It was called Pleasant Valley. And it was back in the 80s that they would have guys like Fuzzy Zoeller and Lee Trevino and people like that, that era, came to Pleasant Valley to play golf. And Cuz Mingolla who owned Pleasant Valley and was sort of instrumental in getting that PGA Tour stop brought to Pleasant Valley would always invite the three sportscasters Lobel, Lynch, and Dennis on Wednesday the Pro-Am to play with some of the golfers. And what Cuz thought was a good idea was to put the three of us with the highest profile guys they could as opposed to the guys that nobody heard of. So, one year I got to play with Trevino, which was an absolute hoot. I’ve never had more fun playing golf in my life. He was hysterical. He had one-liners for every hole. And he would set up a shot and he would do the setup line. He’s standing over a golf shot like this and he’d get it ready to hit it.


Derek Gregoire: Oh, my gosh. So, he’d have jokes in between every shot?


John Dennis: Eighteen of them. Yeah. Every hole he had one. The best story was so we came to those par five and he says to the four of us, “Hey, does anyone want to bet me? Does anyone want to bet me that I can tell you how far I hit this drive within one yard either way?” We said, “You’re kidding?” He goes, “No.” He says, “All I want to do,” he says, “I will call it the minute the ball hits the ground, I will call it. You want to bet?” We said, “Sure.” “20 bucks each.” So, we all take out 20 bucks and we put her on the ground on the tee. He takes the tee and puts it to the $80. He stands up there, wax to drive down the middle. The second it hits, he goes, “281.” We walk out there. It was 281.


Derek Gregoire: No way.


John Dennis: He took the $80, put it in his pocket. He said, “You screwed up. You shouldn’t have let me see it hit the ground.” He said, “You realize I hit the golf ball the same distance every single time. The only variable is if it hits soft and sits down or hits hard and scoots.” He said, “You messed up by letting me see the ball hit the ground.” And he took all the $80.


Derek Gregoire: And you played with Greg Norman at one point too, didn’t you? The Shark?


John Dennis: Yeah. That was at Will-O-Bend. He flew in. That’s when he was the big spokesperson for Reebok and Paul Fireman was the owner of Reebok who also owned Will-O-Bend golf course on the Cape and he brought him in for a big Pro-Am kind of day. And I played with Norman. And Norman did not bring his caddy that day. So, Mr. Fireman gave him his best caddy from Will-O-Bend to go around with Greg. And I think on the second or third hole, we got up to Greg’s ball, and Greg looks at the kid for a yardage. He goes 181 or 182. And Norman leans forward to like this is, which one is it? And I don’t know if he was trying to be a jerk or if he really needed to know which one it is. And the kid says, “182.” Greg says, “Don’t ask me. Tell me.” He goes, “182.” He said, “Thank you.” Then he took out like seven iron and he hit around to the green.


Derek Gregoire: When you and I play, we say somewhere between 150 and 180.


John Dennis: That’s close enough.


Derek Gregoire: That’s close enough. And that’s when you were… So, this is all, obviously, Channel 7 transitioned to – you eventually went full-time on WEEI. That was in the 90s?


John Dennis: Oh, if you’d have to ask. It’s at ‘97.


Derek Gregoire: ‘97. Okay. And so, when I remember the heyday of that show, the Dennis and Callahan show, what I remember was you and Gerry Callahan and Meterparel. That was so funny, so many good laughs. You guys just beat on me the whole time. Well, that had to be an amazing stretch of just life, right?


John Dennis: Well, yeah. And consider what was happening in Boston, you know, the Patriots are bringing up the Red Sox for getting rid of the curse. Celtics won some championships. The Bruins were great. I mean, we often looked at each other during playoff season, you know, Celtics or Patriots or whatever and said, “Can you imagine if we were talk show hosts in Milwaukee, how boring it would be? If we’re talk show host in Cleveland, how boring this would be?” So, we were really, really blessed with the timing of when our show was at its peak and the halcyon days of sports in Boston.


Derek Gregoire: Exactly. Yeah. It’s amazing. Even like talking a mutual friend of ours, Tom Curran, he’s had the Patriots and he was able to like imagine if he was covering the Cincinnati Bengals up until recently.


John Dennis: Cleveland Browns.


Derek Gregoire: Cleveland Browns. Yeah. It’s helped us so much more topics, so many people interested. And during when you were at EEI because this is a conversation we had recently. I took my son to New York a few weeks ago and just my oldest son and I, my wife and my youngest son were actually down near you guys in Venice at our place down there. And basically, we did a lot in New York, but we visited the 9/11 Memorial Museum. It was amazing. Whoever hasn’t gone, it’s worth the trip. It’s really emotional. I remember where I was. It was my last year of college. I was in a marketing class and all of a sudden the event, they just said, “Oh, there’s a plane hit a building in New York. We’re not sure what happened.” And I’m thinking it’s a small plane, which is still drastic, but no idea. Eventually, they said another plane hit and we’re going to stop classes. So, I went home with our roommates in our apartment at UMass Amherst and just watched as those horrible events unfolded. And thinking of the timeline, you must have been on air during all that.


John Dennis: Gerry and I were live on the air and we have in the studio or had in the studio monitors for different news shows and SportsCenter and all that sort of stuff. And one was on, I think it was NBC and Katie Couric, I believe, was doing the anchoring on NBC. And during commercial break, I looked up and obviously, the sound is down in the studio and I see the World Trade Center with a hole in the side of it. What is going on there? We turned it up and just like you and just like most people, they thought it was a commuter plane or maybe a Cessna single engine that fell off course, hit the side of the building. And so, we were on the air and we set up the monitor up there and we came back on. We weren’t all up in arms at that point other than to say something horrible is happening in New York. Apparently, a small plane has hit the building. We’ll keep an eye on it for you. And Gerry and I are going back and forth and we see the second plane hit the second tower and then everybody in the world knew this was intentional, this was a terrorist attack.


And so, of course, we immediately abandoned sports and all the superfluous fun and game stuff we talked about and got into coverage of that. And just prior to that, maybe two weeks before I’ve taken my oldest daughter, Emily, to the school. She was going to NYU down there. And I recall after having unloaded all her gear and bedding and books and shelves and refrigerator into her dorm room, I recall looking out of her dorm window and you could see the Trade Towers from her NYU dormitory. And so, immediately, I said to Chach, our producer, I said, “Here’s Emily’s phone in her dorm. Give her a call. Let’s see if we can find out.” And sure enough, she answers the phone and I can hear in the back, she got the window opened. She’s looking out watching this, and you can hear sirens in the background and they keep an eye. It’s just a phone call. We can’t see anything. And my daughter, Emily, is on the phone with me.


And so, that will forever be etched in my mind that we did about five or 10 minutes with my daughter on the phone talking about what she had just seen. And to this day she hates that recording because she was so unnerved and so anxious and so scared. But what she thought she was sort of nervously laughing with much of what she said and she cringes when she hears that. She’s all, “Dad, I sound so stupid.” I said, “No, everybody didn’t know how to react to something like that.” So, that’s something that I will take to my grave as a memory. You know what that was? That was my generation, almost your generation’s Pearl Harbor.


Derek Gregoire: Got it.


John Dennis: That’s what it was. You know, it was our Pearl Harbor.


Derek Gregoire: Everyone knows exactly what they were doing and where they were.


John Dennis: Exactly.


Derek Gregoire: I know my dad says it was similar for a much better purpose when he’s, he said the two times in his life that he remembers the country being fully united was 9/11 and he said when the U.S. beat Russia in the Olympics. So, those are two. And that was obviously in my younger, I don’t remember that too well. But as you grew through WEEI and got through obviously the Patriots started getting good, you had a gentleman that a few people have heard of, Tom Brady, that you got to know and would join your show, I believe, every week during the football season.


John Dennis: Yeah. It’s called Patriot Monday. And we had a contract with the New England Patriots and we would get three players every Monday or three people every Monday. Brady would be one every Monday. Belichick would be the other every Monday. And whoever the star of the game, not named Brady would be the third guy. So, we have a morning drivetime show. Gerry and I would do 6 to 10 and then the midday show, which was Dale Arnold, generally, 10 to 2 and then Ordway would be 2 to 6. And we got Brady the first year and it was very easy to do. He was very forthcoming. He was fine. He was cordial. He would tell us as much as Belichick would allow him some inside stories, Dale would always get the player of the game, not named Brady, and poor Ordway was stuck with Belichick. And so, as our success, Gerry and my success ramped up, we knocked off Imus for being number one. We knocked off Stern for a while for being number one.


When we went into contract negotiations, we had leverage, and one of the first things we requested, in fact, demanded was before we signed our next three or five-year contract, we wanted in the contract that we continued to get Brady every Patriot Monday for as long as he’s on the team, only because we didn’t want to have Belichick say, “Yes, no, on to Cincinnati. We’ll do what’s best for the team.” So, that’s how we ended up with Tom Brady for 20 years every Monday during football season on our show.


Derek Gregoire: That’s so cool. And basically, in through that, obviously, you get to know him a little bit because I remember going to your house for the Super Bowl when he was on Tampa and you had like text messages and emails back and forth or whatever between you two, which is really cool.


John Dennis: He is a rare bird. And somebody once told me that they knew he was special when he went to his first Pro Bowl in Hawaii very early in his career. And they’re at Aloha Stadium and had a practice and the sponsors of the Pro Bowl whoever the underwriters of the Pro Bowl would bring the kids, the patients from Children’s Hospital to the final practice. And many of them were in wheelchairs, very ill, so on and so forth, but they would bring the kids from Children’s Hospital in Hawaii to Aloha Stadium to watch the practice. And when practice was over, somebody who was there told me about 70% of the guys would make a beeline for the locker room and head to the pool or head to the bar and start partying and drinking and eating and having fun. And they had their families out there. About 30% would stop and sign autographs for the kids.


But only one of all of these Pro Bowl players got down on his knee in front of every single wheelchair kid to talk to them at their own level and ask them their name and signed the autograph. There weren’t selfies in those days. They weren’t taking pictures, but he made it a point not to stand over these kids and say, “Hi, how are you? Hi, how are you?” He got down on their level, shook their hand, talked to them, signed the autographs, went down the line, and was the last one to leave the field.


Derek Gregoire: Amazing. I mean, I’ve always admired his play but his personal character and the way he conducted himself. And one of the things that you had sent me a few years ago, I’m not sure the best way to tee this up for everyone listening and watching but what’s the back story is you had a friend that was unfortunately suffering from ALS.


John Dennis: I can set it up for you.


Derek Gregoire: You’re much better off.


John Dennis: Ironically, his first name was Dennis. He is a friend of mine from Massachusetts, and Dennis contracted ALS, which, as you know, is incurable. Dennis was a huge Patriot fan. I think he had 12 season tickets. He and his buddies would go to every home game. I don’t know if you ever saw the red, white, and blue school bus that used to park in the stadium.


Derek Gregoire: Oh, yes. Yeah, yeah.


John Dennis: That was his red, white, and blue school bus and they would tailgate out of that. And for years and years and years, he was a 12-ticket season hall season ticket holder and just absolutely love, lived, and breathed the Patriots. And his wife called me one day after I’d known that he had been diagnosed and he was sort of going downhill. And I spoke to him, I don’t know, in the couple of weeks beforehand that I knew it wasn’t going well. And his wife called me and said, “Dennis is in the final days and I just thought I’d let you know.” And I don’t know what prompted me to do it, but I texted Tom and I told him the story that I just told you who Dennis is, the school business, 12-ticket, so on and so forth. And he said, “Do you have his phone number?” And I gave his phone number, and that’s the last I heard until a day or two later, Dennis’ wife, sent me a video that Tom had sent to Dennis. And as important as that was for him to take the time to do that and it was very heartwarming to encourage Dennis and say thank you for your support, so on and so forth.


It was March 23rd, 2020, which was the day Tom flew into Tampa to take his first physical with the Bucs and to sign his first contract with the Tampa Bay Buccaneers. He did this from his hotel room in Tampa on the day he was doing all that. So, it wasn’t like he was sitting at home playing Scrabble with the kids. He was busy doing a lot of stuff. They took the time to do this and sent it to Dennis, and his wife told me Dennis saw it and cried. And Dennis passed about three days later but was so thrilled to have heard from Tom.


Derek Gregoire: Yeah.


John Dennis: By the way, that’s not usual. I mean, I know a lot of guys do things, but that is the exception, not the rule.


Derek Gregoire: Well, especially, you put the information together after a while. He was making the biggest career change of his life, leaving the Patriots. It seems like it wasn’t a big deal to us a few years ago but he was with the Patriots best quarterback ever, multiple Super Bowls. Now, he’s signing with Tampa Bay. The same time he’s going to do that, you send him a request and I actually saved it. Could you send me? I’m going to try to play it real quick so everyone can see and listen. This is the text that Tom Brady sent to your friend, Dennis, who was suffering from ALS.


Tom Brady: Hey, Dennis. How are you doing, man? I just wanted to let you know I was thinking about you. I know you’re going through a tough time and nobody is showing more toughness battling this incredible, difficult disease than you. And you know, you’re an inspiration to so many others. I just think your hope and your courage through all this is really something to be admired. So, thanks for being an inspiration for me. I’m a huge fan of yours, and I know you supported me for a long time and I got your back too, man, always. So, you take good care. You enjoy the time with your family and be well, my friend. Hang tough.


Derek Gregoire: Yeah. So, I mean, there’s nothing else to say about it. I mean, think about in the middle of signing with the Bucs, the news hadn’t even released yet and he’s taking the time to make someone’s life a little bit better to help in the last days, which like I said, he died two or three days later. That’s amazing. I’m still waiting for the invite. When you say, “Hey, Derek, do you want to come golf with Tom and I at some point?” So, I’m just patiently waiting. Patiently waiting.


John Dennis: I’ll let you know.


Derek Gregoire: Yeah. I’m waiting. I’m available.


John Dennis: Okay, good.


Derek Gregoire: So, as we get to the end, close towards the end, a couple more topics I want to get into. I guess we’ll get through the deep stuff first, the deep stuff, and then the fun stuff. A fun stuff is obviously the movies and all that, the movies that you’ve been in and the Kingpin and all the cool actors you got to hang out with over the years. But anyone in this world, anyone, almost anyone you talk to had a family member or someone that they know struggle with some sort of addiction, drugs, alcohol, whatever it is, and it can affect anyone at any point and you had shared your – we had talked about your struggle with alcohol. And I guess the question is, looking back, how did you eventually get to the point where you’re like, “I got to get this fix.” What prompted all that? I know and you have a great support system. Your wife, Kathy, is amazing and I’m sure she played a big role but just curious to how that all went down.


John Dennis: Well, I was a highly functional alcoholic. I was not one of those people who would fall down and slobber and pass out, act stupid, and all that sort of stuff. I was a highly functional alcoholic but it became kind of a constant thing and it sort of creeped up on me. It used to be Friday and Saturday night, and I was never in the bars, I was never at clubs. It was always at home. And generally, we’re just sitting down to watch a game. You know, it just became the thing to do. I’d sit down, watch a Red Sox game or Celtics game or a Bruins game, and I’d have, you know, Crown Royal and whatever. And it became kind of habitual and then it became Thursday nights and Friday nights and Saturday nights, and then it grew larger than that. And everybody who has their come-to-Jesus moment with alcohol or drugs has to have a rock bottom story. And when you go to rehab, you sit around with the 15 or 20 people in your rehab class and you are compelled to tell your rock bottom story.


And fortunately, mine was not that bad. I mean, there were people in that room who had a car crash and that killed somebody. Others had gotten divorced and lost their job and were virtually homeless or living in some apartment because they lost everything. Mine was pretty simple. It was opening day 2014, and we were broadcasting live from Fenway Park that morning. On opening day, we have Fenway Park Studios. So, we’re there from 6 to 10. And the game wasn’t until 1:30 in the afternoon and we finished at 10:00, and I go upstairs to the WEEI private box overlooking the ballpark to kill a couple of hours and make some phone calls, whatever. And I’m sitting up there. It’s a beautiful sunlit day. It’s after a terrible, terrible winter and the sun is shining and the sun’s on my face and I’m just relaxing and it’s going to be opening day and the lady comes in to start setting up the buffet and she brings in a bottle of Grey Goose. And I’ve been trying to cut back and I’ve been trying to kind of ween myself. And I had gone maybe a couple of weeks, two or three weeks without it because I knew it was sort of getting out of hand.


I said, “Hey, it’s opening day. I’ll just have one.” So, she leaves and I poured myself one, and then one leads to two, and two leads to three. And that’s the odd thing about my alcoholism. I learned that there are basically two types of alcoholics. There’s the one who thinks about it and craves it and needs it and has to battle it every single day, every single minute. That’s not me. I don’t care about it. I don’t think about it. I don’t want it. But if I have one, I’m off and running. So, clearly there’s this chemical reaction in my body that even if I don’t want it, even if I’m not lusting for that Jack Daniels or Grey Goose, if I have one, it’s like, wow, my brain just goes nuts. And so, I drank and I drank and I drank. When the game was over, I stumbled out of Fenway Park and I went to find my car and I could not find my car in the parking garage for two and a half hours. And I walked every floor and I talked to the attendant. They tried to help me look for it. And I couldn’t find my car and I couldn’t find my car. And I had forgotten the fact that when I pulled in at 5:00 in the morning to do the broadcast, the one lot was closed, the one garage was closed, and I had to go to the second garage.


And of course, I’d forgotten that by 5:00 or 6:00 in the afternoon. I wasn’t even looking in the right garage for God’s sake. Finally figured it out. And thank goodness for that two and a half hours because I think I kind of got a little sober. Sad to admit, I drove home that night and realized that something had to be done. So, I ended up going to rehab for 30 days and everybody told their rock bottom stories and they give you a lot of information and they tell you all these various things but the one thing that stuck with me, Derek, was they said, “Here’s the bottom line. 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.” So, if you understand what I’m saying, you can give up your job and your wife and your kids and your family and your house and your ability to earn a living for that one thing booze or you can give up booze and you can have all those other things. That really sort of resounded with me.


Derek Gregoire: It’s an amazing perspective when you put it that way.


John Dennis: Can I tell you a funny story about when somebody is rock bottom?


Derek Gregoire: Yeah.


John Dennis: He was from Boston and he was the general manager of a restaurant and bar in Boston, and he lived in the Back Bay. And every night he told the story while sitting around. I told my Fenway Park story. He tells his. And every night at closing the bartenders and he, the general manager, and the cooks would sit around and they start pounding booze. And he’d go home, walk home to his house in Back Bay and pass out, wake up the next morning. And because he didn’t have to be at work until later, he’d get up 9:00 or 10:00 in the morning and he would walk his dog. And he had this pattern, looking in the Back Bay and he would walk a block this way, a block that way, a block this way, and a block that way to walk the dog passing three different liquor stores on the way. And he would go into each liquor store with the dog to get nips to even out to shakes. When you’re drinking heavily, you got those morning shakes. And he went into all three liquor stores. He would get nips, fire down one, walk the dog some more, went to the second one, fire down a second one, and a third.


And so, as a result, he was obviously a very well-known customer and they used to give the dog treats and pet the dog and so on and so forth. So, one morning he wakes up and he is sick as can be. He’s got the flu. He’s sweating, whatever. He couldn’t even move. And his wife says, “I’ll take the dog for a walk.” She comes back at half an hour later. She said, “I can’t believe you and I can’t believe you trick me all these years.” He said, “What?” She said, “The dog turned right into three different liquor stores on the walk today.”


Derek Gregoire: The dog?


John Dennis: His dog busted him. So, that’s why he had to go to rehab.


Derek Gregoire: Hey, sometimes it takes a lot of weird circumstances sometimes to get it done. And is 2014, is that the last drink you had?


John Dennis: Actually, I had one little falling out thing for a weekend. I think probably back in, I don’t know, 2017 or 2018. And you know what it was? It was one of those situations where I had no responsibility. I had nowhere to go. And I had been clean and sober for a long time. I say, what, I can probably have one. I haven’t had one for a long time but I’m just going to have one just to see, you know.


Derek Gregoire: What I can do?


John Dennis: Prove to myself that I’m really not addicted to the stuff. I had one. I go again. And that was the one kind of confirmation that I can’t have one.


Derek Gregoire: And you even at that point, you’re able to stop it right away and just…


John Dennis: Oh, yeah. The older you get, the worse the hangovers are too.


Derek Gregoire: Yeah.


John Dennis: It used to last half a day, then a day, and then two days. So, it’s not worth it.


Derek Gregoire: Yeah, I know. Like I said, a lot of people have asked how you’ve been doing over the years, and I say I probably spent 40 different days on the golf course and had dinner. And I said, it’s always been Diet Cokes, and I’m not a big drinker, as you know, myself. So, it makes it easy but, yeah, congratulations. I know that’s something I’m sure, like you said, it’s not on your mind every day but like you said, you still have to stay away from that one because one becomes ten.


John Dennis: Exactly. I think the expression is one is too many. Ten is not enough.


Derek Gregoire: Yeah, that’s true. That’s a good way to put it. So, thanks for sharing that. I know it’s not the easiest thing I’m sure to…


John Dennis: No, I don’t mind it at all.


Derek Gregoire: Obviously, you learn from it but it’s just a tough, tough time of life I’m sure going back, looking at those days, and glad to see you doing great. But during that timeframe of over the years, you became friends. I believe it was, was it through the broadcast? Maybe we’re friends with the Farrelly brothers who directed a bunch of different comedies?


John Dennis: Yeah. I actually emceed a Bruins charity event at Will-O-Bend, the golf course, for Cam Neely’s foundation, The Cam Neely Foundation. And Peter and Bobby Farrelly, the director of Kingpin, Something About Mary, most famously Dumb and Dumber, were there. And when the event was over and everybody’s going their separate ways, Peter and Bobby Farrelly came up to me and said, “Hey, we’re thinking about doing this movie called Kingpin, and it’s about bowling. And we needed an announcer to play an announcer’s part a role in the film. Would you be interested in doing that?” I said, “Is that a trick question? Of course, I would be interested in doing that.” So, 1995 or ’96 and they flew me out to Reno, Nevada for ten days to shoot Kingpin. And that’s how we ended up in the movie.


Derek Gregoire: So, I’ve picked your brain on this. I’ve seen obviously, I believe you’re in it for like 45 minutes.


John Dennis: Oh yeah. There’ll be a second of me by the end of the film if you haven’t seen it. By the way, if you watch it, I still get residuals. I get like a nickel if you rent Kingpin.


Derek Gregoire: Really? You got like a check? You still get little checks here and there?


John Dennis: I’ll tell you what, when the first came out, I was getting big checks. I mean, it depends on it being relative, but I was getting like $7,000, $8,000, $9,000 every couple of months. And then as the film kind of passed, it went into replay, went on to cable and all that sort of stuff, checks dwindled, dwindled, and dwindled. So, I think my last check I got was for $7.35.


Derek Gregoire: Wait. A half a cup of coffee. Not bad.


John Dennis: Exactly.


Derek Gregoire: So, in this time of the story, obviously, in movies you met a lot of people but Bill Murray is probably one of the most prominent. I don’t know if you golf. Was it him you golf with or was that Randy Quaid?


John Dennis: I golf with Randy Quaid who was the Amish guy. I golf with him, by the way, he’s a three handicap or was a three handicap. He was a great player. But the Bill Murray story was funny. He decides one night we’re going to go after shooting. We’re going to in Reno, Nevada and we’re going to go play baccarat. And nobody really knew how to play baccarat. I don’t even know if that’s how you pronounce it. But Bill says, “I’m going to teach us all to play baccarat.” So, Bill Murray, John Dennis, Peter Farrelly, Bobby Farrelly, and one other guy go to the baccarat table and Bill sitting here and Peter and Bobby are on either side and I’m sitting on the left of Bobby. And across the room, there is this guy who’s holding all these papers like a stack of looks like papers or pictures or folders or stuff and he is staring at Bill. I mean, just staring at Bill. And Bill doesn’t make eye contact, but he says to the five of us, the four of us on the table, he said, “Stalker at 11:00. Do not make eye contact.” And so, whatever and he stared, he started, and he stared.

And finally, the guy walks over and he comes up to Bill and Bill looks at him, goes, “Mr. Murray, I’m very sorry to bother you but I’m your biggest fan. I have every clipping, every photo, every movie you’ve ever done. And I’m wondering if it wouldn’t be too much trouble if I could just have an autograph.” And Bill pushes his chair back and he stands up like this. What’s going to happen? And he turns around and he puts his arms around the guy and he kisses him on the lips.


Derek Gregoire: No.


John Dennis: And lets him go. Never signed the autograph. The guy takes his photos and he just drifts off into the casino. He’s never seen again.


Derek Gregoire: I don’t think I heard that one. That’s hilarious. The guy just never said anything. He just walked off?


John Dennis: He was just stunned. He was like, in shock.


Derek Gregoire: And that’s a true bowling alley out in Reno, right?


John Dennis: It’s called the National Bowling Center. It’s like it’s so big, 110 lanes or something. Maybe. I don’t know if that’s right. It sounds right, but it’s so big, if you sat at one, it almost goes over the horizon


Derek Gregoire: That’s crazy.


John Dennis: Gigantic.


Derek Gregoire: That’s crazy. And you were in a few others, if I remember right. Was it Me, Myself and Irene and Shallow Hal?


John Dennis: Me, myself, and Irene. I was a police detective. What else?


Derek Gregoire: Shallow Hal.


John Dennis: Shallow Hal. That’s it. In fact, if you watch Shallow Hal when Gwyneth Paltrow was in this gigantic fat suit comes into the restaurant, you’ll see the maître d behind the desk is Darius Rucker from Hootie & the Blowfish.


Derek Gregoire: Yeah.


John Dennis: And he’s the greeter and I’m the maître d. I’m standing there with the menus, and Darius Rucker says, “Oh, welcome. Glad to see you. I see it’s a rose among two thorns. Jon will take you to the table.” So, I just come walk this way. They followed me out and go. But as we walk out, there’s this lounge lizard at the end of the bar who goes like this and is looking at Gwyneth Paltrow as she walks by and that’s Gerry Callahan.


Derek Gregoire: I didn’t realize he was in there.


John Dennis: If you rent Shallow Hal, look for the bar scene when they come in and Darius Rucker greets them. I have the menus. I take them to the table and Gerry is staring at her as she walked by.


Derek Gregoire: Before we closed out your movie career, well, there could be more to come but I wanted to show, there’s a quick trailer that I know there’s a story to from Kingpin. So, we’re going to play the end of it real quick and see what the story is behind it.


John Dennis: Okay.


[Kingpin Movie Trailer]


Derek Gregoire: What happened? How did that even take place?


John Dennis: Well, I’ll tell you what, moviemaking is not as glamorous as you think. It’s the exercise in hurry up and wait. You know, you hurry up and you wait, wait, wait. You reset this, reset that. Even simple things like condensation on a wine bottle between takes, a guy will come over and spray it with water. So, the condensation is, you know, on the present. And so, we’re doing this scene where I’m interviewing Woody Harrelson after his bowling performance. And we’re standing there, the two of us, on a two-shot. And basically, my line was, “So, what have you been doing all these years, Roy, since we lost track of you?” And he goes, “Drinking, a lot of drinking.” So, I’m supposed to look uncomfortable and haltingly say, “Well, are you still drinking?” And he goes, “Oh, no, no, no, no, no, no, no. That’s behind me. Well, wait, why? Are you buying?” And we must have done that 20 times. And it wasn’t that hard. I mean, it was easy. It’s all it was. It was literally 15 seconds. And we did it again. We did it again and we did it again.


I was like, “Bobby, Peter, what’s going on?” Now, Bobby and Peter are on either side of the camera. And he said, “Let’s do it one more time.” And so, I sort of like lost my concentration and Woody looks at me and says, “No, no, no, I’m not drinking. That’s all behind me now. Well, wait, why? Are you buying?” And I lost my line. I couldn’t think what it was. And so, I’m facing this way and I lost my line and I went to look at Peter and Bobby to save me. And Bobby goes, “Cut. That’s the one.”


Derek Gregoire: No way.


John Dennis: Hey, I had forgotten my line and turned to the camera to look at Peter and Bobby on the other side of the camera to help me out and they go, “That’s the one.”


Derek Gregoire: That’s so cool.


John Dennis: That’s what you saw at the end of the trailer. It was a mistake.


Derek Gregoire: That was a mistake that they used for the final cut and it made to the actual trailer. That’s awesome. Well, I mean, obviously, you’ve had an amazing career. Looking back, I’m sure it’s a lot of awesome memories. Do you have any regrets over the years or was it like anything you would change, like looking back or did it all work out?


John Dennis: I’d stop drinking sooner probably.


Derek Gregoire: That’d be a good one, right?


John Dennis: No, no, no. No regrets at all. No, I’ve been blessed. Sure beats a steel mill, and I enjoyed every moment of it.


Derek Gregoire: Yeah, I know. And obviously, like everyone who has asked and curious, you’re doing great. You, obviously, haven’t drank in years. And if you look behind you, if my house is on the other side and between myself and John and Mike, I just want to make sure everyone knows I had the smallest house of the three. I’m down there the least but I am 44 years old, so maybe in the future, I’ll get my retirement years. We’ll be spending more time down there. It’s obviously been great getting to know you over the last couple of years and just thanks for coming on and sharing your story. I think there’s a lot of inspiration around the quotes. I think that quote you shared around…


John Dennis: Give up one thing for everything.


Derek Gregoire: I love that. I love all the stories. I’m sure a lot of people were brought back to so many events that they remember growing up from different sporting events in 9/11 and Tom Brady, the Red Sox, Celtics, golf. Any other final stories we missed that are worth sharing? I have one other one, just one more. You might not even want to share it but I thought anyone who plays golf, I feel like I try to tell the story and I can never tell it as good as you do, but the one where the par three uphill. Do you know what I’m talking about? Is that a story you can share?


John Dennis: I think so if I leave some names out.


Derek Gregoire: Yeah. Leave some names out but you tell it better than I can.


John Dennis: I was playing in a charity event at Ferncroft and there were three of us and there were just three of us in our group but they added in the dreaded single, you know, the one guy that nobody knows to our foursome. And there was an uphill, I think it’s 17. I might be wrong. I don’t think they switched the nines or not, but I think 17 at Ferncroft, there’s an uphill par three and we all hit our ball up there. And I preface the story by saying my playing partner had the best moment and the worst moment of his entire golfing experience within a minute of each other. So, we all hit our balls up for the green. You really can’t see the surface. You can see the top of the flag, and we walk up there and then one ball is in the trap and two balls on the green. And the single who was added to our group is looking around, looking around. He’s behind the green now and he goes, “Oh, here it is. I found it. It’s all right.” So, whatever. We don’t think of anything. And he chips the ball on the green. We walk over to putt. His original ball was in the hole.


Derek Gregoire: Unbelievable.


John Dennis: He hit a hole in one but he couldn’t find the ball. Never thought to look in the hole and cheated and dropped the golf ball behind the green and said, “I found it,” and they chipped it on. We said, “Get out of here.”


Derek Gregoire: See you later. Your best moment in golf and worst moment in a minute.


John Dennis: What a dope.


Derek Gregoire: That’s crazy. How do you tell your first hole-in-one story? I’m sure he tells that differently, right?


John Dennis: I know. Exactly.


Derek Gregoire: Well, hey, thanks so much, John. Honestly, I really appreciate you taking the time. It’s been awesome. You know, I love seeing you enjoying your retirement. You and Kathy have been so helpful to us down there. Kind of keep an eye on the place when we’re not there. And I’m sure you’ll be coming up north for some golf this summer, right?


John Dennis: I’m staying here through the past the 4th of July with a big 4th of July tournament here. I’ll probably come up in mid-July. So, if you’re here before that, let’s play. If not, I’ll see you up there.


Derek Gregoire: Awesome. Thanks so much. Appreciate you as well. Thanks for joining us, John.


John Dennis: Thank you.


Derek Gregoire: Take care.


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