The Graeme Roustan Show: Ted Leonsis

The Hockey News' Money and Power 2025 hockey business annual is available at THN.com/free, 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 Washington Capitals owner Ted Leonsis.

Here's their full conversation in The Graeme Roustan Show:

Read along with an excerpt from their discussion:

W. GRAEME ROUSTAN: Is part of your overall philosophy on life and business just to focus on the future?

TED LEONSIS: I think that playing offense is a much better way to be a leader than playing defense and trying to protect what you have. I think we just saw that with our political environment in our election. You rely on polls, you rely on history and what the crowd is thinking, and you end up being wrong more than right. So, innovation, having a growth mindset and being able to use real data to move forward is what’s incumbent on us as leaders. The NHL has done a remarkable job of moving the state of the game forward while still paying homage to its history.

I think commissioner (Gary) Bettman has done a fantastic job of balancing that. I just got the agenda for the board meeting next week. There’s going to be a whole afternoon session on innovation and digital and how it will affect our business and the game. Then it was followed by Colin Campbell, who you can’t say is innovative going to the future, but he’s all about the game itself. That balance is what you need as an organization. You have to pay homage to the essence, the DNA of the brand, of the product and of the game itself, but if you’re not innovating, you’ll die. You’ll shrivel and go away.

We’re celebrating our 50th anniversary. I go, “That’s unbelievable.” Most Fortune 1000 companies, the ones that were founded 50 years ago, are not alive today, but the Bruins are celebrating their 100th. I go, “That’s what’s amazing about the durability of the leagues.” It’s why the values of our teams and franchises have exploded since the pandemic. The movie industry and sports, concerts, games, we were affected dramatically. Then, when it was lifted, you could go to games. It was blessed. It came roaring back to the movie industry and they came roaring back to our arenas for our games, which signalled to really smart money that this is a business that’s built to last. It’s not a fad. There’s something endemic in it. The competition, the live nature, the communal effect, the importance of being able to get that content out everywhere, both terrestrially and digitally. Every NHL team now is valued at over a billion dollars. I paid $85 million for the Capitals 25 years ago, and now Columbus is worth over a billion dollars.

WGR: When we talked four years ago, you were talking about gaming, about IT and technology, things that other owners really weren’t thinking about, but you were. Is your role more of a visionary today than it was 25 years ago?

TL: Well, 25 years ago, I was getting America online. When I first got online, it was 1991. I think there were less than half a million people around the world getting internet connectivity, and it wasn’t internet connectivity. At AOL, it was illegal, until 1995, to get onto the internet. The internet was built and owned by the federal government here. DARPA in Virginia basically created the internet, although vice-president Al Gore at the time took credit. But it was a way to connect military sites and research institutions together.

At AOL, we built a private internet, and that sounded great, but then it was, “How do we teach people to get online?” So, we looked to the past and said, “People send and receive mail. Let’s make an easy mail product.” Then, we had to commercialize it: “Welcome. You’ve got mail.” Instant messaging. I sent the first instant message to my wife. It delighted her. It was a little love message. We were constantly looking at, “How do you take technology and innovation that all these tech companies were funded for and make it accessible to people?”

"Playing offense is a much better way to be a leader than playing defense." - Ted Leonsis

I would always say, “He who gets to a billion first will win.” In 10 years, AOL went from half a million customers to 10 million households. When we acquired Time Warner, we were in 33 million households, which was one of three every American households. I’d go to parties, I’d go to events, and I’d go, “One, two, AOL customers.” Every household had three or four people, mothers, fathers, sons and daughters. So, scale always mattered to me. Getting to a billion, as an entrepreneur and evangelist, it always takes longer than you expect to get there, but then when you get there, it’s always way bigger than you predicted.

With the NHL, I remember when I first bought the team 25 years ago thinking, “This is an underappreciated asset and business.” I remember listening to local media, and it said, “There’s 15,000 people that care about hockey in this community.” I’d say, “They’re just not getting it.” I saw that we’re social people. We crave live events to share an experience. I use that as my job. I have to set a culture. You have to prioritize, and you also have to be very clear on what victory is.

What I’m most proud of, over the last 25 years, is that we have a culture now. We’re a destination. We bring players in here. We brought a lot of new players in this year, and I asked to meet with them. I asked them, “You’ve played for L.A. You’ve played for this team, that team. What do we do right, and what do we do wrong?” It was really interesting and continues to be interesting that everyone wants to play here now. Everyone wants to be here.

We’ve had a great run, but no one remembers what happened five years ago. Yes, we’ve had an unbelievable record. When we won our 1,000th game, they put up the stats. We won the division championship 50 percent of our time owning the team. We were in the Southeast, then we moved to the Metro, and everyone said, “Well, you’re going to get your ass kicked now.” We had a good team. We have a great record, but no one cares. That’s the thing about sports. You’re only as good as what’s going to happen next year. I want to make sure that we can be generationally great. We can have a securitized future.

We’re going to have to innovate and change and do things differently for the next 25 years. The fan base will change. The delivery of media is changing dramatically. The competition for people’s time is going to change dramatically. Everything is moving so fast, so rapidly. I’ve tried to create a, “Let’s not have a bad day.” Because if we have a bad day, we’re going to have a bad week. If you have a bad week, you have a bad month. You have a bad month, it’s a bad quarter. Bad quarter, bad year. It’s over, right? So, setting culture and making sure that we can major in the majors is what I think ownership’s job is. It’s certainly what my job is.

"All I could think of was, 'Oh my gosh, he’s going to blow his knee out playing basketball at my house.' " - Ted Leonsis on Alex Ovechkin

WGR: Let’s go back to when you drafted Alex Ovechkin.

TL: I remember I had a full-time job at America Online. They were doing the lottery pick, and I was tangentially aware but kind of unaware. I’m in a meeting. My assistant comes in and says, “Commissioner Bettman’s on the phone.” I said, “You know, I have a meeting. I’ll call him right back.” My assistant comes back and says, “You need to take the call.” I go, “Hello,” and the commissioner says, “I’m here with so-and-so from Ernst & Young, and the Washington Capitals have won the first pick in the draft.” Now, that wouldn’t happen today, but it was like, “Oh, great.” So, I called George McPhee, and he goes, “Yeah, it’s already leaked, and I heard about it.” I said, “That’s great. Who are we going to take?” There wasn’t the reporting and the like compared to today. Honestly, I’ll never forget this. They said, “Well, there’s two players. There’s Alex Ovechkin and Evgeni Malkin, and they’re both great players. One’s a center. One’s a wing.”

I do remember our scout in Russia telling George and then telling me, “They’re both going to be Hall of Fame-great players. They’re both very gifted and special. Malkin’s a center, and we need centers, but there’s something magical in Ovechkin. Mostly, we see his pace, his energy, and he scores. He performs better the later the game goes. His beat is great.

We go to Carolina, and we announce Alex. It’s the first time I’ve ever met him. It’s not like I was in Russia scouting him. That’s how it was back then. I meet him, and we’re going to have a season-ticket-holder party at 5 o’clock, and I get there at 5:05. Alex is already there. He’s eating cantaloupe. We have fruit for people, and I don’t know if he had ever eaten cantaloupe this sweet and this fresh. I’m just assuming this because he was shooting down the cantaloupe. He stood outside and shook every person’s hand. I remember saying to Dick and my son, “Who is this guy?” He’s inhaling everything. His energy, his charisma, he was like the greeter, you know? He wasn’t handled. It was him.

He stayed with George McPhee for the first couple of weeks, and he didn’t speak the language very well. George called me and said, “I’ve got to get rid of this guy. Can you take him for the day so I can do some stuff with my family?” He dropped him off at our house, and now it’s the first time I’m going to spend time with Alex. We’re going to have a little barbecue, and my son was probably 16 at the time. We barbecued. We went swimming. We played basketball. Next thing I know, he’s playing hard basketball with my son and his buddies, who were players. All I could think of was, “Oh my gosh, he’s going to blow his knee out playing basketball at my house.”

He went swimming, and I spoke to him in the pool 1-on-1. I said, “You know, we’re a bad team, but by design. It’s going to take a while, but we’re going to build the team around you. Believe in us. We’ll believe in you.”

It’s been remarkable to have a player, it’s been 20 years, he’s never asked to be traded or to fire this coach. He’s always been incredibly focused and loyal. If he breaks Wayne (Gretzky’s goal) record, I don’t know if there’s another player in (the four) major pro leagues to play for one team. LeBron (James) has played the most games, has the most points, but he played with four teams. Wayne played for a lot of teams. To have that kind of stability all the way through and to have the reliability that he has is impressive. I saw a stat the other day that he’s been available to the team 96 percent of every possible game.

For more of the text Q&A with Leonsis, more interviews and 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.