The Leafs still need another big break, and they’ve set themselves up to get it

Every summer when draft time rolls around, we get to talking about the value of selections and the probability of prospects turning into serviceable NHL players. To the surprise of absolutely no one, picks from the beginning of the draft generally do much better than the ones in the later rounds. 

But even with that simple piece of information in mind, we know basically every team has players turn out who were selected beyond the first round, and some are fortunate enough to eventually get a star out of the mix. 

There are a number of examples of teams that have been built to championship caliber by unearthing a late-round steal or two. I won’t get into all of them here, but I just want to talk about how the Leafs, in midst of rebuilding, are hopefully due for their own. I’d argue it’s going to be one of the most important turning points that will put them over in terms of contention. And now that we’re under way with hockey season at all levels, we’re reminded of how big a development year this will be for so many of the Leafs’ prospects, notably those who’ve made a step from junior to pro, and then more specifically their recent later-round selections now with the Marlies. 

Without getting into every single team in the league, there are some notable instances of later-round finds that, if subtracted from the picture, would shake their organizations big time. Montreal made strong playoff runs over the last half decade with P.K. Subban, a 2nd-round 43rd overall selection who emerged as, at times, the best defenceman on the planet. Now Nashville will likely do the same. Kris Letang in Pittsburgh was taken in the 3rd round at pick number 62, Duncan Keith at 54. Even Shea Weber, for all the criticisms he’s taken this summer, has been elite through much of his career. He was taken 49th overall in 2003. 

These aren’t incredibly long-odds selections in terms of developing an NHL player, but these guys are, or have been, stars. Elite players. Speaking of Stars, Jamie Benn was selected by Dallas in the fifth round.

I realize I’m not breaking any ground here. These players’ stories are well-documented, and like I said, the list runs much longer league-wide. But it goes to show that accumulating picks like Toronto has been doing is a smart approach in that it gives you ever-increasing odds of hitting on something like the above-mentioned, and that’s hopefully on the verge of proving itself. That’s what this Leafs rebuild will really need in its next step, and likely will get. We just don’t know who it’ll be yet. All that said, with some key picks from those last couple drafts now moving into their first pro seasons, we might be in the process of finding out.  

As great as the Leafs’ approach has been over the last twenty-four months or so, the idea of a straight-line build of “Develop Matthews, Marner, Nylander, and fill in the space around them” won’t be the way this all plays out in real-life. At some point, an unlikely star is going to have to emerge, perhaps one who even manages to surpass one of those three. 

And I’m not just talking about picks who turn out to be great value. That’s something else entirely. I mean, if Connor Brown turns out to be a regular 35-point player for Toronto – which isn’t at all out of the question – that would be huge. A sixth-round steal. The same goes for a player like Hyman. If the team can fill out parts of their lineup over the next while with good possession-driving young players they’ve drafted themselves, that’ll be an incredible testament to their approach. It’s the right way to build. But I’m still thinking bigger. 

In a way, this ‘Shanaplan’ eventually needs to go off the rails, but in a good way. Something unexpected needs to happen, in the form of a player exceeding every scouting report written about them like the examples above have done. Add to that list Gaudreau, Parayko, and so on.

It’d be particularly nice if something like this happened on the Leafs blue-line, much like it has in the cases of Pittsburgh, Montreal, Nashville, and Chicago. In this iteration of the league it seems like such an extremely difficult position to shore up, and trading to make a huge improvement there just doesn’t seem in the cards. Can someone like Travis Dermott or Andrew Nielsen – whose career paths to date aren’t all that different to Subban’s at that age, for example – emerge as a top pairing guy? That isn’t meant to put pressure on them, or make any style comparison to P.K. himself. I just want to illustrate that, at some point in the jump from junior to pro, there are prospects that unexpectedly hit in a big way. It should happen here too.

Up to this point – and keep in mind we’re early in this build – the Leafs’ key players have been picks from the top of the draft. Matthews, Kadri, Nylander, Rielly, Marner are all former top-ten selections, while even the acquired core pieces, like JVR and Gardiner, went 2nd and 17th respectively in their draft years. But another player will eventually move into that group and surprise us all.

It might seem absurd to say a team that just won the draft lottery for Auston Matthews should be due another strike of fortune, but this is different. The Leafs are clearly aware of pick volume in later rounds being a smart approach, and have played the odds by accumulating so many selections in the last couple drafts, increasing their chances of developing a surprise star. Now we see the rubber hitting the road, as this season looks to be a very important one in seeing who might start to emerge.