Ahead of the 2023 NHL Draft, Maple Leafs GM Brad Treliving discussed his decision to keep Sheldon Keefe as head coach for the 2023-24 season, his first month on the GM’s chair in Toronto, his involvement in the draft, and the status of contract negotiations with William Nylander and Auston Matthews.

What was the process like in deciding on whether to move forward with Sheldon Keefe as head coach?

Treliving: I really enjoyed it. It was difficult and probably uncomfortable at times, but I am really excited and look forward to working with him. Probably the next question will be relative to contract status. We will deal with that at the appropriate time, but Sheldon will continue on. I am excited for him to do so.

When you are in the middle of talking to players about their futures in the organization, how much value is there in having some familiarity and comfortability with the coach?

Treliving: I think Sheldon has a really good relationship with his players. They all think he is a good coach. I think there is a really strong bond.

What I took away from it: There is a real strong belief both ways. There is belief from the players in the coach. There is belief from the coach in the players.

It was unique. When you have been in the business as long as I have, usually, you have come across people somewhere. We really haven’t. We needed to build that connection.

Certainly, there was a great deal of respect both from the players’ side and coach-to-player.

You thought he was a good coach from afar, but what stood out to you in the process of getting to know him?

Treliving: I think there is a real focus. He has come into this market at a young age as a young coach. It is not an easy job.

I think he has a bright mind. He is open to change. He is strong in his beliefs, but he also doesn’t think he has all the answers.

One of the things we talked about is that I firmly believe we are all sometimes better in our second jobs. You see it sometimes with coaches. I think there is a little bit of that. I have talked about my relationship with Kyle. [Sheldon] has worked with Kyle for a long time. But sometimes a little bit of newness or freshness can help — a little bit of change.

There are a lot of things that I came away with there. We probably met for 17 hours over four or five days. Probably by the third day, he was like, “Maybe I don’t want to stick around with this guy.” Once I didn’t chase him out of there, I thought maybe he’ll stick around.

I came away thinking, “This is a really bright guy.”

When you say 17 hours, is it you and Sheldon sitting in chairs staring at each other? Do you go golfing?

Treliving: Yeah, it’s just meetings. There are three buckets to it. You have to develop a relationship. There is a getting-to-know-you part. And then you dig in a bit into the philosophy, the team, the players, and where he sees it going.

There is a strategic part. You start going through some video. How do you play? There might be a little bit of a change in how we play, but how does he see the game? It’s a little bit more of the bricks and mortars — defensive-zone coverage and all of those types of things you have to go through.

There is a step and stage that you have to grind through.

Where do things stand with the open assistant coaching job?

Treliving: We are in the process of evaluating everything else. It is not always perfect when the manager comes in three weeks before the draft and there are a whole bunch of things.

I dealt with Sheldon. We are evaluating the staff now and how it all fits. We have an open position. We are evaluating everything else. It is a long way of saying we are working on it.

Have the restrictions been lifted by Calgary for you to be involved in the draft?

Treliving: Brendan has been dealing with that. I have not been dealing with anything draft-related. As we stand here today, I will be at the table once Calgary has made their selection. I think Calgary selects at #16. I will be at the table shortly thereafter.

Are there any other restrictions you are faced with for the draft? Have you been in the draft meetings?

Treliving: I haven’t been in the draft meetings, no. Really, I am just not involved in the draft up until today and getting clarification on the [draft] table.

Where do you stand on your first-round pick and whether you are going to keep it?

Treliving: We pick at #28. As good teams do — and this team has been a good team for the last little bit — you move draft capital when you are trying to win. We have moved some draft capital over the last few years. It would have to make a lot of sense to move the pick.

I don’t think we are flush with bullets to move up. Probably, when you are handicapping it, you are picking or potentially moving down. If there is something that makes sense to move the pick, we would.

At some point, you have to put some groceries back in the cupboards. I think there is a fairly good bet we are picking at #28.

How was the visit with Auston Matthews in Arizona?

Treliving: Less humid than Nashville. It was good. I had a good chance to visit with him. That relationship and that dialogue continued. We certainly got down there and spent a few days with him.

We all know the files that are open. We continue to work away at it. It was really good to spend some time with him.

Have there been any assurances made to the core group about remaining together?

Treliving: I don’t think there are ever any assurances in this business, you know? We have really good players. We have two who have a year left on their contract that we’d like to re-sign. We are engaged in that. You just keep working away at it.

How confident are you that you are going to get Auston Matthews and William Nylander under contract?

Treliving: I am always confident until proven otherwise. I am positive by nature. The dialogue has been good. You keep working away at it.

Listen, there has been lots of interest in it. I get it. I will never have a public discourse on contracts, but we are working away at it. Hopefully, we get to a good conclusion.

How different are you as a GM after going through a similar situation with Johnny Gaudreau?

Treliving: We all learn from experiences. There are things you are not going to comment on. There is some stuff that happens in those situations that lends itself to the end result.

At the end of the day, you learn from everything. With every experience you have — in any walk of life and in any job — you think you are wiser. You maybe avoid some potholes that you stepped in prior. You are better for the experience.

From an organization’s perspective, how important is it to get clarity on Auston Matthews and William Nylander on July 1st or as close to it as possible?

Treliving: The sooner, the better, right? When you know where things are at, you can climb better, right? If you know it is going to be raining tomorrow, you maybe pack a jacket.

Having clarity always helps. Is it the be all, end all? No. You have two sides that are going to play a piece in this puzzle. We would certainly like that. We are certainly trying to work towards that. If it happens or not…

July 1, the world doesn’t stop. I feel very confident that we are going to get both players signed until proven otherwise. Hopefully, it is July [1], and if it is not, we will keep working away at it.

It looks like the next few weeks are the fertile time for trades. After that, the cap gets used up for a lot of teams. You don’t have forever to decide if you want to act or not. How do you balance that when wanting to extend someone like William Nylander while also knowing that there is a bit of urgency to it?

Treliving: I would say this: You work the process. If there is nothing out there to make the team better, it doesn’t make sense to make a trade just to stand up there and say, “Hurrah, I made a trade.”

Our focus, when you talk about Willy, is strictly to get him signed. You are always talking to people. That is the job. The job of the manager is to know, A) What is going on in the league, and B) Are there avenues to make your team better regardless of who it is?

The priority is to sign the player and to always have your ears open for whether there are opportunities to make the team better. Sometimes, the timing doesn’t match up. That is the process you do. You can’t manufacture it if it is not there, either.

What is the plan for Matt Murray?

Treliving: Matt Murray is a good goalie. We can all agree that probably the biggest challenge has been availability in terms of injuries.

I look at it now, and we have three good goaltenders — really good goaltenders. We have Joe [Woll], the young guy who finished off well. I’ve learned sometimes those young guys finish off well and it doesn’t necessarily mean the start is going to go well, right?

We have three good goalies. It is a position where we have good depth. Like anything else, we would be open to looking at different things, but if at the end of the day, we go to camp with three good goalies, good for us. That’s how I look at it.

What are you going to prioritize in the UFA market?

Treliving: We have a lot of UFAs. It is a little bit of, “Let’s see what happens in the next couple of days.” It is a unique situation.

We have talked about Auston and Willy, and although they are not free agents this year, it goes into next year’s planning. We have some players who are UFAs this year. Let’s see where that goes, what we can and can’t get done, and where we can fit it all in. We will then have a better idea come July 1.

Generally speaking, what do you make of the UFA class?

Treliving: We have been at a minimal-growth cap. Everything is squeezed. Everything is tight. You see more players extending for a longer period of time. There is less availability.

I would just classify the market as having some good players but there is more quantity. You don’t know. We have a number of UFAs. Are those players going to be signed between now and Saturday? It could change.

We will probably know better in the next couple of days, but there will be good players out there.

Have you had your first phone call yet with Flames GM Craig Conroy as opposing GMs?

Treliving: I have talked to Conny a lot, yeah. He is a good man. He is going through it. I always say that there is a difference between the co-pilot chair and the pilot chair, right? Landing the plane is different than the guy cheering you on to do it.

He is doing good. We have had some discussions. Like us, he has a lot on his to-do list.

Is it a disadvantage at all that he knows your every thought on all of the players he might be talking to you about?

Treliving: I think he knows what I think of those players. We have had those discussions a lot, but there is movement around the league, right? I don’t think it is too unique to this.

Whether it is managers moving, assistant managers moving, or coaches moving, wherever you have been, you have feelings on players. His feelings and my feelings — like anybody else, everyone has their own. He has a lot of good players over there.

After adding Shane Doan, do you foresee making any other additions to your staff?

Treliving: Doaner has been a really good addition. He has dug right in.

In all honesty, what I have said with staffing: With everything that has been prioritized until July 1, we will deal with that after.

What I have learned in my short time here: There are lots of really good people. We have been utilizing everyone. We will cross that bridge once we get through the next couple of weeks.

What has surprised you most about this job so far?

Treliving: It has been pretty much Groundhog Day. It’s up early, go to the office, and I am drinking out of a firehose right now. It’s not so much because of the market. It is the timing and the files we have to deal with.

It has been cool. I am living in a place where I have a Fat Bastard Burritos down there that’s good to eat. I thought that was pretty cool. I have a couple of those, get up, and get after it the next day.