Thoughts on the Maple Leafs heading into a fascinating summer

I’ll still be weighing in with written articles on Sportsnet.ca as events warrant this summer, but since this is one of my final official submissions – and the last is always my trademarked “two sentences on every free agency signing” – I figured it makes the most sense to leave with Leafs Thoughts as we head into the true off-season.

We’re post-draft and pre-free agency at the time of this writing, and yeah, there’s a lot to work out for ol’ Brad Treliving. To those who’ve followed my NHL coverage this year, which regularly checked in on the Leafs, I appreciate you.

Once more unto the breach, dear friends.

The William Nylander conundrum

Instead of starting with Auston Matthews, who will almost certainly be signing a new deal to stay in Toronto, let’s start with William Nylander. With the Matthews situation trending towards one outcome, the Willy domino will have a great effect on the state of the Leafs in the years to come.

As of now, it’s being reported Nylander and the Leafs aren’t close on dollars, which leaves things up in the air.

• I don’t think this contract gets done July 1, or even within a couple weeks of it. The 10-team no trade list that comes into play July 1 is not that limiting for the Leafs, given Nylander is an elite forward who’ll command attention from any number of teams. If they want to trade him, they can still trade him. They’ll work themselves to a conclusion here and ignore that soft pressure point.

• If it isn’t wrapped up by early September, they should trade him. The Leafs have gotten sub-par performances from guys coming into camp late. Nylander mostly stunk the year he signed at the 11^th hour before December 1 at the beginning of his previous deal, and Mitch Marner wasn’t great the year his contract status was up in the air. You’d like this team to enter a new season without questions marks, knowing the group they have is the group they’re going to have. And frankly, September is far enough from now that if you can’t work it out by then, you aren’t going to work it out. So if you’re looking for a rough pressure point, there it is.

• Nylander is probably going to get a deal that starts with nine (though I’m sure his agent is asking higher), and in my opinion, both camps are best-served with shorter term. Why is it assumed these days that you should lock up every quality player for the max-length, which is damn-near a decade? A shorter-term deal – say two or three years? - would allow Willy the chance at another big payday at around 30, before his age truly scares teams, and after the cap has shot way up. This would also help the Leafs through another few years of their “win now” window, where it’ll either work (and they’ll win) or they’ll be all too happy to say goodbye to everyone involved. It would keep his cap hit down – a key component here - rather than paying for the years the cap will inevitably go up. And frankly, it will keep the guy motivated, which has been a question for him at times. An eight-year deal for an eight-year-deal’s sake makes no sense.

• One thing I really don’t like about a potential Nylander trade: it gives Marner a pile of leverage right before he’s eligible to sign a new deal next summer, and this is a guy who took the Leafs to the cleaners the last time he had a deal come up. (I will never forget that within weeks of signing his last alarmingly-high deal, Marner tweeted out a personal promo video to Drake’s Champagne Poetry that included the lyrics “And if the last negotiation had you feeling out of pocket, well, this is the perfect time that I empty them sh*** for sure, You owe that s*** to the boy, yeah.”)

Anyway, with Nylander gone – an elite winger – the Leafs couldn’t then also lose the forward they play the most often who threatens 100 points each year and defends at an elite level. It’s one thing to “shake up the core”; if you lose Willy, the threat of losing Marner makes you look at a “break-up of the core” and they’d certainly pay just about anything to avoid that.

In conclusion with all this: give me a three-year Nylander contract for $9M per (even up to $9.5M per?), and I think everyone makes off happily here.

Matthews’ deal

Length of term is where the drama lives with this one. Our producer on Real Kyper and Bourne, Sam McKee, has been upset about one simple thing here: other superstars for other teams have shown their commitment to winning by signing eight-year deals for below their market value, so why can’t Matthews?

Other people may say: why should he?

Hockey’s salary cap has mangled incentives and forced players into awkward spots, which is where the Leafs star finds himself now. You should be able to get paid what you're worth and still compete for a championship (as in other sports), but with a flat cap for so many years, that’s almost impossible.

It’s also worth noting that Connor McDavid and Nathan MacKinnon are kind of winning-obsessed freaks (that’s a compliment), and I don’t think being smart about how you structure your deals timing-wise, as Matthews wants to do, means you don’t care about winning. He’s pushing for career flexibility to an extent, and we see that in every other major sports league.

The best thing here for both parties is to again take the lower cap hit and years and re-assess after a three year deal -- which would expire four seasons played from now -- and try to win while these great players are prime-aged.

One other consideration here, for Leafs fans who want all the Matthews term possible: He scored 20 fewer goals this past season than the year before, and at times looked … off, we’ll say, throughout the year. His wrist has acted up to a concerning degree for a guy who relies on his shooting. Is there not also some security in giving a guy three or four years if in fact the rest of his career were to look like this season, or possibly worse if injuries were to incessantly nag at him into his mid-30s? Eight years would come with a higher number, which brings long-term risks of its own.

The return of Sheldon Keefe

Treliving is intent on not making change for change's sake, and I will say, this is where it helps having someone in charge who's viewed things from the outside looking in.

From the view of another organization that prepares to play against the Leafs, you focus on the things they do well, and you try to stop those. The last thing Treliving would want to do is come in and shuck the very things that made his Flames nervous on the other side of the puck. The Leafs possesses elite game-breakers, and they’re always well-prepared by their coach -- Calgary would’ve noted those things.

Treliving seems to understand the desire for change in Toronto, but change to a 111-point team that won a playoff round isn’t exactly easy. It’s like getting to a low handicap in golf -- at some point, taking the next steps to being better gets really hard, and rarely involve overhauling what got you so close. Keeping the fundamental things the same isn’t the worst idea, which seems to be what’s happening here with Keefe.

Free agency

Fascinating time ahead. My prediction: there’s big D available, in Scott Mayfield (6-foot-5), Carson Soucy (6-foot-5”, Ryan Graves (6-foot-5), and even Nikita Zadorov (6-foot-6) available via trade, and I think the Leafs will have interest in getting bigger on the back end. If you look at who they’ve got returning -- Timothy Liljegren, Conor Timmins, Morgan Rielly, even Jake McCabe isn’t a big-big guy -- and I think they’ll make that a priority.

What’s going to be most interesting to me is how they balance two things. One, is that the Leafs' core isn’t physical, and the team was undeniably aided in ultra-competitive playoff series by the physical willingness of a guy like Noel Acciari, Ryan O’Reilly’s ability to play in traffic, and Luke Schenn’s eagerness to answer the bell. They’re going to need some of that, but I personally don’t think it'll come in the form of one nuclear player (say, Ryan Reaves), but rather from a host of guys who play as a priority, but have some bite to them. It’s also extremely dangerous to build a hockey team when you're looking for those attributes, rather than valuing them as add-ons.

I want to see how the Leafs balance the desire for size and physicality with the reality that they need way more offence right now. They scored two goals in seven straight games to end their season, and finished ninth in the league in scoring. Ninth never sounds bad until you remember only 16 teams make the playoffs, and those are the teams you’re competing against.

How can the Leafs find more scoring beyond their core -- particularly with the pending departure of Michael Bunting -- while also adding playoff-style teeth to their game?

In all, Treliving walked into a mountain of files to deal with, and while he’s handling them one by one, their time-sensitive nature means it can’t happen at a leisurely pace. UFA season is upon us, and the shape of next year’s team is about to come into silhouette focus. Finding out just how different it will be from seasons past is what keeps the Leafs near the centre of the league’s attention in the days ahead.