Fresh off signing a six-year contract extension, Toronto Maple Leafs President Brendan Shanahan joined Prime Time Sports to discuss his decision to extend his stay in Toronto long-term, the organization’s progress to date under his watch, the process of getting over the hump in the playoffs, the cap challenges the team is facing, and answering to the Rogers/Bell board.

Was your deal up?

Shanahan: Yeah, my deal was expiring in July. The team had approached me probably over a year ago. Maybe not the best negotiator for myself, I said, “I probably shouldn’t be saying this, but I’m not going anywhere. I want to stay. I want to see this through. I am enjoying the job and I’m very passionate about it. I love it here.” But the time wasn’t right for me then to start talking about my own deal. I just said, “When the time is right, we can sit down. It won’t be very difficult or I don’t anticipate it being very difficult.” We talked about it a little bit through this season and a little bit just before the playoffs. I just said, “Again, I am not going anywhere. We’ve got enough of the makings of a deal that when the season is over, whenever it ends, we’ll make it official.”

You said the job is not finished. Where do you think you are in terms of the job — the big job? 

Shanahan: It’s funny. When you do something like this, everyone wants to know how many years and where exactly are you, and what percentage. I focus less on that. I focus on the process in which we are getting there, the people that are making the decisions, and how they come about making their decisions. When we do make a decision on a player, whether it’s a trade [or what have you], usually my first question to Kyle is, “Tell me about the process of how we got here? Who have you spoken to?” I think we are an organization that shares those same values.

What I would say is that I had a player ask me at the start of year what I think about or worry about sometimes and where I see our development. I said, “I think we are certainly in the window where we can win. I sometimes wonder whether or not we’ve got enough scar tissue. I sometimes wonder whether we’ve got enough experience.” But you can’t get it without doing it. You can’t get scar tissue without scraping your knee sometimes. You’d love to just show up and win and everything seems easy, and there are some teams and some examples where that has happened, but for the most part, when I look around at different sports, it usually comes with a little bit of heartbreak and some hard lessons.

And then you look and say, “Do we have the grit and do we have the determination to see this through, or are we going to change plans and go a different direction, or are we just going to quit?” I think that’s what we are going to do. I think we are poised and still pointing in the right direction. I do think that the style with which we played, I saw advancement. I saw growth with many of our individual players. But, ultimately, we didn’t get the job done and we haven’t gotten over the hump yet. I am looking forward to that.

When I look at our sports and other sports, the sad, sorry news is that you’ve got to just stick with it. You look at teams like Washington and Ovechkin, and San Jose right now, it has been a long time for them. St. Louis has never won a Cup. You look at some of these teams and you just say, “I admire their perseverance.”

You were ahead in a first round series against a team that may well win a Stanley Cup. You can look at it different ways.

Shanahan: I look at it in the sense — People say, “It must hurt for you to see Boston advancing,” and I actually say, “I prefer it.” I don’t prefer it because I feel it gives us any comfort. I don’t feel that way. I prefer it because it’s a bit like an open wound and it’s like pouring salt into the empty wounds of our team and our players. I think an angry team, when it makes it more personal, it makes it part of the learning experience. You want it to hurt more.

You’ve played on a winning team with a lot of veteran players. Can a player with scar tissue impart that to younger players, or do you think that is overrated?

Shanahan: I think it helps. I think it helps to have someone around that has been through it. I had a conversation before the playoffs started with our team and that was one of the messages I had for them — that Ron Hainsey can’t give this to you. Mike Babcock can’t  tell you about his Stanley Cups. I can tell you about it, but you have to do it yourself to go through it. The one thing I said to them that I really do feel, especially when you see some of the teams playing right now and some of the players that have Stanley Cups on their resume, it is almost like figuring out how to open a safe. People can tell you what it feels like or how it sounds, but you have to do it yourself. You have to sort of solve it yourself.

But the real secret is and the real good news is, once you do it, you can never unlearn it. I think our players have to learn it themselves. I think having players on the team with Stanley Cup experience can help, but ultimately, it is up to the players themselves.

I love seeing, even with the Marlies, that these guys won last year. I don’t think it just has to be at the NHL level. Whether it’s playing NCAA or junior A or the AHL or in Europe, I think learning how to win at anything, you start to learn what the costs are, what the price is you have to pay.

You were part of the conversation with Mitch Marner’s agent. Give me a sense of whether you guys think you’re going down the right path.

Shanahan: It was a positive meeting. I have a lot of respect for Darren Ferris and admiration for Mitch and how he’s developed and how he’s rounded out his game— not just his offensive creativity and prowess, but penalty killing and his overall game has improved so much.

It was a positive meeting. Beyond that, you’re not going to hear anything from Kyle and I or Mitch’s camp, I believe… That’s what we talked about today — there is no point in playing this out through the press. I had said to Darren, “We are going to have some news later today and I am going to be doing some press. If I get asked, I don’t want to lie. I said, ‘Are you okay with me telling the truth that we met?’” He said yes.

A lot of decisions have to be made. There are cap issues here that have to be addressed. The Mitch Marner signing is not going to make it any easier. Is there a board somewhere in your office or Kyle’s office where you guys have kind of mapped this whole thing out?

Shanahan: First off, five years ago when I came, over time, you start to figure out that we’ve got some issues and some problems. Everyone knows the story of how that went down and what we did. I remember someone saying to me at the time, “Oh boy, I hope you hire some people and bring in some help and you guys can all make the team good again so it is peaceful in the city and everyone is happy.” I said, “I’ve got to warn you about something: The better you become, the less peaceful it is and the more anxiety there is because each decision means more. You still have problems. They’re just better problems.”

I remember someone saying this year, “You’ve got a real problem. How are you going to sign those three young great players?” I said, “If you told me four years ago that was going to be my problem, I’d say sign me up.” As long as we are hopefully a Stanley Cup contender, we will have cap issues. Toronto should just get used to that. It doesn’t mean we aren’t prepared. It doesn’t mean Brandon Pridham doesn’t have a board, a two-year plan, a six-year plan. We have all of those things. It is not easy. Not everyone is privy to the plans or the workings that Kyle is doing, but it will always be a challenge. That is just something that we should just accept and embrace. Just about every team that has a consistent ability to challenge for a Stanley Cup will have cap issues.

The minute you do the Tavares deal, the calculations begin, correct? And the Matthews deal falls after that.

Shanahan: We’ve hired a fantastic guy from the NHL that used to work in Central Registry in Brandon Pridham, who was one of our first hires. It is not without challenges. It is not without adding some more grey hairs to all of us. But it is not something that we wake up one day and say, “How did this happen?” You build contingency issues for different contracts and different players. Things that are out of your control, whether it is injuries or callups or things like that, it is always a moving target. But that is just something that the city of Toronto should just say, “So long as we are a good team…” If we are not dealing with cap issues, we are probably rebuilding.

President is an interesting title. Every hockey fan understands the coach’s responsibility and what he does. They know what the GM’s responsibility is and what he does. Most people have absolutely no idea what you do.

Shanahan: Neither do I! [Laughs]

Take a minute and tell the fan base what a day for Brendan Shanahan involves. A normal day, what is your real responsibility?

Shanahan: I don’t know if I can answer it. I was doing another radio hit and I was saying, if I took you through one of my days, it would be really boring, bad radio. I just called George McPhee a few days ago after he moved from GM to President. I said, “Hey George, it’s Brendan. What do you do? I don’t understand your job.” He said, “You’re about the fifth guy to call me and ask me that. I know you’re being facetious, but I tell everybody it’s the same thing Cam Neely does and JD does and Shanahan does.”

There was a time in the NHL where your coach was your GM, and then all of a sudden, somewhere in the 80s, some team said, “We are going to have a coach to focus on the coaching and a manager to focus on the managing.” Ten years later, every team had that sort of process. I think the NHL is going in this direction to a certain extent. It is not immediate. There are some really, really good teams and really capable people that don’t have this setup. To the extent that I can be a communicator between ownership and our management team so that they can focus on the managing and the coaches can focus on the coaching… I can take care of some of the details that I don’t want them to be worried about or bothered with.

I think communicating with your ownership group is really important. It is something I learned while I was at the NHL: In the absence of communicating with them, they are going to get their information from somebody else, and it maybe somebody else that doesn’t have all the facts.” I’ve had really good support from our ownership group.

In any course of the day, it does change. I like to think that I am not as capable as the people that I’ve hired but I am somewhat fluent in all of their positions and to the extent that I can ever help them when I need to help them, I try to. I think one of the things that attracted me to this job when I came here is that it does move around a lot. The details and the responsibilities change day to day and week to week.

As far as answering what I do every day — I don’t know. You tell me.

With this ownership group or structure, not all teams have this structure. There are places where it is one person. You are reporting to a board here with members from two rival telecom giants.

Shanahan: This is my experience from the day I got here: I don’t know what they do when they’re at their other businesses, but when it comes to their sports teams, they are Torontonians. They have children. They go to school here. They have family here. They live in Toronto. Their interests are aligned. I have seen them work really well together and help me solve problems with the Maple Leafs. I’m sure Masai can give other examples with the Raptors as well and all of the other teams as well. When it comes to their sports teams, their interests are aligned and they have been fantastic partners and owners.