Maple Leafs Sports and Entertainment's CEO discusses his history in the media business, the extremes of 'tribalism' and what it will take for the Leafs to end their Stanley Cup drought. The Hockey News' Money and Power 2025 hockey business annual is available at THN.com/free [https://thehockeynews.store/products/print-subscription], featuring the annual 100 people of power and influence list. W. Graeme Roustan, owner and publisher of The Hockey News, sat down with special guests for peer-to-peer conversations also featured in the issue, including Maple Leafs Sports and Entertainment CEO and alternate governor, Keith Pelley. Here's their full conversation in The Graeme Roustan Show: Maple Leafs Sports and Entertainment's CEO discusses his history in the media business, the extremes of 'tribalism' and what it will take for the Leafs to end their Stanley Cup drought. Read along with an excerpt from their discussion: W. GRAEME ROUSTAN: You’ve been in the media business forever. You started at TSN, went on to run and be the president of TSN. Your resume, it’ll take me an hour to go through it, but needless to say, there really isn’t a media executive position in Canada that you haven’t had at some point or another. KEITH PELLEY: I think I’ve been in the right place at the right time, working with some incredible people. It’s been a privileged career. I’ve enjoyed every minute of it, and I’m having a lot of fun right now. WGR: When anybody reads your bio or does a Google search on you, they see that you worked in the newsroom, the media room, doing editing, directing and producing. You really got your fingers in every single pie in the media business. Then, you worked from that role to becoming the president of TSN. That’s pretty special, isn’t it? KP: Yeah, the vision that Gordon Craig had regarding TSN, he was far ahead of himself, as well as the late Jim Thompson and Rick Brace. I owe a lot to them. I was producing NFL football for Fox in the States, and Rick Brace called and asked if I wanted to, as he said, “Come out of the cold.” I was travelling, at that point, north of 270 days a year. I was producing hockey. I was producing football. And I loved being a producer. But when Rick asked me to come in and be the vice president of programming at TSN, I jumped at the opportunity, having no idea what I was doing. I had no idea what EBITDA was. I didn’t know how to read a balance sheet. I was a production person. So, there was a big, steep learning curve. Like I said, if you didn’t have people along the way, like Rick Brace. I worked with, at that point, Phil King, who I’ve recently brought into MLSE. Phil was an accountant by trade, so I learned a lot from him. I learned the business side of it and always loved television. I originally wanted to be on-air and did some on-air work but realized that I was really bad at it, so I got behind the camera. The media was great, but I always loved football. My first foray into running a team was back in 2004, when I was the president of TSN, to run the Toronto Argonauts. "If you’re part of a team, you understand what “game day” means." - Keith Pelley WGR: Running the Argonauts, it was outside of your comfort zone, wasn’t it? What did you rely on? KP: I knew absolutely nothing about running a franchise. I’ve always believed that if you work hard, have a great attitude and have some intellect, that knowledge is a distant fourth – unless you’re a doctor or a dentist. I spent a lot of time reading. I spent a lot of time late into the wee hours of the morning reading everything I possibly could about the Argos and the league, and I started to talk to as many people as I possibly could. It was learning new skills, but it’s like anything…you take the same skills and just transform them into a different part of the business. Then, it’s just about learning that business. We had some great success at the Argos, and I knew for the first time, if you’re part of a team, you understand what “game day” means. You wake up every morning and you go, “It’s game day.” Right? Well, at MLSE, it seems like every day is game day. WGR: Then, from there, you go to Rogers, don’t you? KP: Yeah, I went to Rogers as the president of Rogers Media. I worked at Rogers for about four or five years. During that time, we did the NHL television deal with Gary (Bettman) and his team. That was 12 years, then it’s expiring. It’s coming up in a couple of years. No doubt, the conversations are going to happen pretty quickly, but that was a game-changer for Sportsnet. Sportsnet, at that particular time, was so far behind TSN. WGR: After Rogers, you leave North America, and you run the PGA European Tour. You moved to London, and you’ve left your hometown of Toronto. KP: My wife came home, I guess I told her that we had this opportunity, and she said, “Well, let’s go.” I said, “Really?” She said, “Yeah.” So, we picked up and moved. We lived in London, in a spectacular place called the Wentworth Estates. We had nine years, which were magical. We travelled the world. I’ve been to 48 countries. We counted up a couple of weeks ago, my boy and I. It changed his life, and it changed my daughter’s life. W. Graeme Roustan and Keith Pelley [https://thehockeynews.com/.image/c_fit,h_600,w_600/MjExODk2MTMzNjU4ODE0NDQw/pop_pelley4.jpg] W. Graeme Roustan and Keith Pelley The only time in Europe when I was running golf, which is an individual sport, that you had the tribalism like I had at the Argos and that currently exists at MLSE was during the Ryder Cup. We ran the Ryder Cup in 2018 and then in 2023 in Rome. We beat the Americans both times. I remembered what that felt like. It was unbelievable. That’s the feeling I want to get here. I never had that chance to experience 2017 TFC winning. I didn’t have the experience in 2019 when the Raptors won and galvanized the whole city. Can you imagine if the Leafs had won? What is it now, 57 years? WGR: Well, it’s the longest drought of any NHL team. That’s a lot of pressure on the players, the coaches and the staff. But at the top of the pyramid, isn’t that pressure for you to deliver a Stanley Cup? KP: Sure, it’s a lot of pressure, but it’s a lot of fun. Being part of teams, whether you’re actually involved in the team or you’re a fan, the rollercoaster is incredible. The highs are unbelievable, and the lows are devastating. In Europe, you see that. One of the very first games I went to was Manchester City versus Liverpool, and it was a game at Wembley. I was with my boy. I bought a Manchester City scarf and a Liverpool scarf, and we thought we would wear them. Where we were going, it was into this suite called the Bobby Moore Suite. We walked in, and they said, “You’re not allowed your colors in here.” I said, “I’m sorry?” They said, “You’re not allowed to wear your colors.” I had no idea what they were talking about, but they were talking about the scarves. "It comes down to culture and believing that you’re all on the same page." - Keith Pelley When you see English soccer, the tribalism is unbelievable. The unwavering passion is incredible. In Toronto, that passion exists as well. The greatest thing about Canada is it does have a polite passion. You can still sit beside a Montreal Canadiens fan. You’re not going to fight with that person. But you’re right, there’s a lot of pressure, and there’s a lot of opinions. Social media has changed the way that we look at news and information now. You just have to believe that you have the right strategy. You have to try to take the noise out, just stay with your principles and build the chemistry and culture that you believe can create the winning formula. The competitive balance in the National Hockey League is incredible. Gary’s done an amazing job creating the competitive balance to the point where the margin of difference is very, very small. So, then it comes down to chemistry. It comes down to culture and believing that you’re all on the same page. I think, right now, that’s where we’re headed with the Leafs. At least, I hope so. WGR: It almost comes down to one shot, one goal, one shift. You can get to the second round or third round just from one. It's so competitive out there. KP: Everybody’s trying to win. In all four of the sports that we run, we’re all trying to win. How can you be just a little bit better than your competitors? That comes back to preparation, having the right culture and the right attitude. That’s what we’re trying to build. For this and more interviews with a deep look into the world of the hockey business, check out The Hockey News' Money and Power 2025 issue, available at THN.com/free [https://thehockeynews.store/products/print-subscription].
