5Q: Tim Leiweke, President & CEO of Maple Leaf Sports and Entertainment

Tim Leiweke uses the words 'win' or 'winning' more than a dozen times in our conversation. It's a message he's been drilling into the collective psyche of Toronto FC, Raptors and Maple Leafs fans since he took over as boss of Maple Leaf Sports and Entertainment last summer, and he's loathe to stray far from it.

By most accounts it appears to be working. Once seen as mission impossible, few can dispute the fact that his drive to win has been contagious. First, he wanted his own crew so there was a shuffle at the top echelons of the company. Then there were the splashy Leafs contracts with Phil Kessel and Dion Phaneuf. After that, Leiweke sent a jolt across all MLSE franchises — and the soccer world — earlier this year by doling out $100 million for international soccer superstars Jermain Defoe and Michael Bradley.

All the while, there's buzz around a $120-million BMO Field expansion, which could possibly bring events such as the NHL Winter Classic and the Toronto Argonauts. How all the changes and plans unfold remains to be seen, but one thing is for sure: Leiweke, who was the top gun at Los Angeles-based Anschutz Entertainment Group and hired to rejuvenate the embattled sports franchises here, has our attention.

It's been said you're famous for elaborate courtships, tell me about the Defoe and Bradley deals?

For Defoe, it wasn't a moment. It was more a three month-long, extended, courtship. And so it took a couple of months to get to the right place with him and to get to the right place with (his club) Tottenham. I don't think there was anything really sudden there. Bradley was a bit more sudden. He was a deal done in a week.

What was the reaction from your board spending $100 million on these players?

The board was quick and quiet. Look, our board wants to win. People forget we've already spent $120 million on two hockey players: Phil Kessel and Dion Phaneuf. This is not unusual for our board. They are very committed to anything that ultimately helps us win. So this was not a long conversation.

You've said spending that kind of money would make fans of the Leafs and Raptors pay attention and take notice. Have they?

Like all businesses, you tend to follow patterns. You tend to display a philosophy and a culture, not just in one aspect, but across the board. If I'm a fan of the Leafs or a fan of the Raptors, I think I would get excited about the fact that we will not hesitate to do what we have to win. Our owners are very committed to winning. They are focused on championship teams. They're prepared to take great risks in order to help us get there. That bodes well for all of our teams in MLSE.

Well, it is a big risk. How do you expect to recoup that money and, more generally, how do you expect to grow revenue?

Sell more tickets. Sell more sponsorships. Expand BMO Field.

And? Can you flesh out the BMO Field expansion?

Obviously, we're looking to expand the stadium to 30,000 seats (from roughly 22,000). There's a demand that will ultimately justify that. We've sold 17,000 season tickets and now have to be more focused on group tickets and single tickets, and ticket packages to expand our base of support.

But based on how quickly we sold the 17,000, we feel pretty good about expanding our season ticket base to 24,000, which we are going to be able to do if we move into a 30,000 facility. But I also think we're looking at adding sponsors, we're looking at new jersey sponsors. We're very comfortable that by next year we will be able to make this deal a break even or better proposition.

There's speculation MLSE will buy the Argos as the first step to securing an NFL franchise

People speculate this is about the NFL. It's not. It's just a simple fact that currently BMO Field is owned by the city. It is the city's desire that if we renovate it that the renovation is something that ultimately has dual purposes, solutions, not only for our ability to continue to grow TFC and MLS, but they also want us to be able solve the long-term Argos issue.

What are the big challenges to a dual-use field?

There's scheduling issues, there's turf issues, there's the fact that the CFL field is larger than the MLS field. When it's all said and none, we'll figure out how to overcome the challenges and make this a reality if that's what the city wants us to do.

Speaking of changes, what is the status of the Raptors?

We're definitely going to rebrand the Raptors. What we won't do now is do anything to take away from the team, the momentum they've created, the progress we've created. So our focus right now is to get into the playoffs. That's our goal. We're not going to do anything to complicate that. Once our season is over, and I'm hoping it's May or June, then we'll be in a position of having a conversation about where we're going on our new brand.

What kind of rebrand?

I'm afraid everyone's going to have to hang for a while. We're in the middle of working on that. We'll have something to talk about this summer. If we win the fans will understand if this brand needs to freshen up, especially as we go to our 20th anniversary and we host the entire league in 2016. They get it.

How did you develop your relationship with Drake, and why do you think he connects with fans?

I'd been in the music business before I came here so I knew of Drake and his management team. We developed a relationship when I first got here and it's just grown from there. Drake has a good relationship with Masai (Ujiri). He's one of the most popular entertainers in the world. The day we announced the NBA All-Star game coming to Toronto we had about 3 billion hits in two days. I'll attribute a lot of that to Drake. He understands social media, he understands fashion, trends, and he understands Toronto. He's a perfect complement to help us figure out what to do with this franchise.

What are the challenges of managing brands under one umbrella in the Canadian vs. U.S. market?
It's colder. You're nicer. I like living here.

And? There's nothing different about the sports culture between the two countries?

No, I don't think there's any difference. If we win, everyone's happy. For us, it's just about winning.

You've really stressed winning. You've also said there's not a day that goes by that someone in Toronto isn't mad at you. Tell me about that.

I think the fact that we're having a conversation about winning means it worked, didn't it? There's a method to our madness here. People have opinions about pictures on walls, parades. We're sitting here talking about winning. That is different for this organization and that's what we want to accomplish.

What do you want your leadership style legacy to be?

Winning.

And? Anything else?

That's it. Everything else takes care of itself if you're winning. Every day we get up and try to build a new culture here that is totally focused on the absolute, wonderful opportunity we have with this marketplace and our owners to win. That's what we strive to do. We understand everything else, financial results -- gross revenue, EBITA -- everything else will fall in line if we can make that our passion.

What's your favourite sport to watch?

I think of these teams equally; I love these teams equally. I happen to be a big fan of the NHL, the NBA and MLS because I've been involved in these leagues for, in some cases, almost 35 years. I don't have favourites.

What sport do you like to play?

I like to play golf. I'm really bad at it and I don't have to worry about who wins.

*Interview has been edited and condensed