There’s no worse feeling than thinking you’ve prepared for the draft more than any other year, waiting for the team you cover to make their picks and constantly saying to yourself, ‘Who?’

But that’s what it was like for me watching the Montreal Canadiens on the second day, and I’m sure it was like that for many fans as well. The instinct is to sit back and think that the scouting staff is the one in the wrong. But after some reflection, I think it’s the people on the outside who are wrong. And we may have to change our way of thinking, not demand the Canadiens do the same.

Drafting highly ranked players doesn’t guarantee success

To everyone looking at their draft list (even the Consensus Rankings on EOTP), you will see highly ranked players that the Canadiens passed over with several of their picks. But just because a player is highly ranked doesn’t mean he should be the actual pick.

Let’s go back to the 2012 NHL Draft. The Canadiens had the third overall selection and finished the draft with what was believed to be one of the best classes of the year. I remember reading a Hockey News Draft Preview and seeing every Habs prospect taken being ranked above where they picked him. Four of the prospects they picked had first-round buzz.

Not much remains on the internet from the 2012 Draft. But I did find this recap of the Canadiens’ haul:

Grade: A Galchenyuk, Collberg, Thrower and Bozon are all guys who will be making differences for this team both in the near and distant future. You have to like a draft which has players that can step in and make differences immediately and ones that you know will develop into impact players as well.

That wasn’t the only source praising the Canadiens.

The Canadiens left press row saying “nice pick” nearly every time the words “Montreal go ahead” were uttered over the PA. Canadiens final draft grade: A

We know what happened. It didn’t work out. There were circumstances that led to this not panning out, like Bozon’s health issues, but the only NHL player — not a regular — other than Galchenyuk from that draft was Charles Hudon.

That same year, one team didn’t have people thinking they had a great draft. They were given a lower grade. That team was the Pittsburgh Penguins. Their first five selections all made the NHL and four of them are now Stanley Cup champions. They may not have drafted superstars, but they drafted contributors to championship teams.

Derrick Pouliot, Olli Maatta, Teddy Blueger, Matt Murray, and Oskar Sundqvist earned the Penguins a C grade, but they are the ones who had the better draft.

You don’t just want to be the team that wins the draft the next day. You want to be the team that wins the draft after five years — or sooner if it’s obvious enough. They usually aren’t one and the same.

The draft is about hitting home runs

When you get to a certain point of prospect depth (and with about 10 picks for three straight years counting next year, the Canadiens are at that point), you don’t need bodies. You want players you think will be contributors at the NHL level, regardless of how long it takes them to get there.

You use the draft to hit home runs. Singles will always be available on the open market; you don’t need to draft them. This Canadiens team has signed David Sklenicka, Joël Teasdale, Otto Leskinen, Alexandre Alain, Alex Belzile and Nikita Jevpalovs in the past year at smaller dollar figures to take the spots the majority of drafted prospects end up occupying: minor-leaguers with that hint of NHL potential.

The club just declined to sign Scott Walford and Jarret Tyszka — two players with decent chances of becoming NHL players, but close to a zero percent chance of being difference-makers at that level. With 21 prospects already added to the organization, and nine more (at this point) coming next year, you don’t need to commit to bodies right now.

The contract limit is about to become a real problem — and so is the salary cap

Entry-level contracts last one to three years. Up until 21 years old, the entry-level deal is three years. That means that approximately 30 players from the 2018 to 2020 drafts are going to be vying for one of the 50 contracts available to the Canadiens. The team has 40 contracts of the 50 limit signed currently before free agency begins. Next season, they are already committed to 24 players, and that’s if they sign no one to a multi-year contract.

We’ve already established that singles can be found anywhere. Now we add the wrinkle that the Canadiens will only sign the best of the best of their prospect pool. It serves them no good to be safe. They could have a whole draft of Walfords and Tyszkas and not sign them. That’s not the goal. Trevor Timmins is focused on swinging hard. He may miss, and get Nikolas Koberstein or Arvid Henrikson. But then you may get a Jake Evans, or an Alexander Romanov, or a Cayden Primeau.

You could sign people to fill roster spots at any point, often for close to the league minimum or minor-league contracts. Finding significant NHL contributors is the challenge, and when every team is looking for those, you sometimes need to go off the beaten path.

The other issue is that you want to scatter your entry-level contracts. If you have too many restricted free agents needing raises and new contracts in the same year, your salary cap will become an issue. As it is, 2021-22 will see Jesperi Kotkaniemi, Ryan Poehling and Cale Fleury end their entry-level contracts. 2022-23 will see Josh Brook, Cayden Primeau, and Nick Suzuki’s deals end. Now keep that train going every year, and you run into problems.

I’m not saying that the 2019 NHL Draft by the Canadiens is guaranteed to turn out great, or even good. But reasoning that the draft was bad because they didn’t pick players who were known commodities in Junior is not a good enough reason.

The Canadiens aren’t merely looking for professional players. At this point they’re looking for players who may have one skill and can develop the rest of their game. They are going to have to make some tough decisions on prospects going forward like they did with Walford and Tyszka. The 2019 Draft aims to make those decisions easier — for better or for worse.