LEAFS NEED MOAR FIRST ROUND PICKZ: Who’s gonna give them up?

By #jontent (@yakovmironov)

The Leafs are already selecting twice in the first round, and again with the very first pick of the second round, and the nine more throughout the rest of the draft. Generally speaking it’s probably safe to say that the Leafs don’t actually need to acquire any more picks.

That’s the sound and reasonable logic, but on the other hand, for those of us that have spent months following this draft class (and it’s not a great one) and creating monthly lists of our ideal draft orders it seems inevitable that settling for just two or three from our top thirty lists seems like a bit of a let down, especially considering the large gap between 1st overall and the 30th and 31st picks overall. My math isn’t what it used to be but I’m pretty sure that’s the biggest gap possible in the first round.



This is a pretty common way of getting another first round pick, and the Leafs having the 31st overall pick, it seems like it would take very little to at least slide into the later part of the 1st round. The idea of having the Leafs step to the podium three times in front of what will largely be a Leafs fan audience in Buffalo has to be an appealing thought.

Last month Tom Hunter made the argument for moving up in his post on why the Leafs should be aggressive at the draft…

Last year when the Leafs “Belichick’d” the draft they were rebuilding a system, this year they should be looking to provide quality, not quantity. Now let me first say that I understand the argument behind trading down, drafting 18-year olds is a crap shoot and in theory the more picks you make, the more likely you are to hit on one. That said, looking back at just one year ago to the 2015 draft, the teams had the best first rounds look to be the New York Islanders and the Philadelphia Flyers (discounting the Oilers who bungled their draft up yet still win because of McDavid). The Islanders and Flyers both left the first day of the draft, with not one but two prospects that shot to the top of their farm system, and they did so by being aggressive. Having already selected the prospect some called the best defender in the draft in Ivan Provorov, the Flyers saw a prospect thy liked and traded up to get him.

In the case of the Flyers, they gave up the 29th and 61st (picks to move up 5 spots). The Leafs own similar picks using either the 30th, 31st, 57th, or 62nd overall picks (picks 57 and 62nd have been adjusted because of Arizona not signing Connor Bleackley and the Coyotes receiving a compensatory pick). If the right player is there, this seems like a worthwhile approach, but using any of the draft pick value models that exist, it was a significant overpayment by the Flyers to make that move.

I discussed draft pick value models vs. perceived prospect value a couple of weeks ago, and how it was better compare Konecny’s value based on where he was placed on consensus draft rankings…

Using Platinum Seat Ghost’s Aggregate Draft Rankings from 2015, which compared a number of popular draft rankings, we see that Konecny was 16th overall. A value of 530, which still gives the advantage to the Leafs. We also see from these rankings that there was significant variance on where Konecny was expected to go. If he went 33rd overall as one service ranked him as, he would have carried a value of 380, but counter to that, if he went 7th overall as another service predicted, he would have carried a value of 700, meaning the Leafs would have actually received less value in return.

Even using that model there was an overpayment, but a smaller one, and it’s foolish to believe that some overpayment wouldn’t be wouldn’t be necessary to move up in the draft. That being said giving up two picks within the top 62 to move up a few spots isn’t something I can be sold on this far in advance. On draft day if Dante Fabbro still hasn’t been selected with the 23rd pick, I would quickly change my mind. Each team has their own draft list, and if they have a player who’s ranking make it seem like they are actually getting a bargain by trading up I’d assume they’d leap at the opportunity.

That being said, I prefer the idea of roster players and B and C level prospects as kickers to move up a few spaces. The Leafs have marginal roster assets like Peter Holland, Frank Corrado, Colin Greening, and Matt Hunwick who seem like affordable roster player inclusions in a deal. Considering that late first rounders may have a higher ceiling than those players, but low odds of reaching that ceiling, a pick and player combo might be reasonable compensation.

Prospect wise the Leafs are stocked with second tier prospects like Stuart Percy, Scott Harrington, Josh Leivo, Freddie Gauthier, Viktor Loov, and Rinat Valiev who could all be used to improve a pick as well, especially ones like Loov, Leivo, Harrington, and Percy who are viewed as ready to challenge for a roster spot.


Perhaps better still is the idea of maintaining the Leafs current draft picks, and leaping into the first round solely on giving up a roster player. If we look back to last season there are a couple of examples of that happening…

  • The Bruins added the 13th overall pick along with Martin Jones and Colin Miller for Milan Lucic at half salary.
  • The Bruins also added the 15th overall pick along with 2 2nd rounders for Dougie Hamilton
  • Hilariously the Islanders received the 16th overall pick and the 31st overall for Griffin Reinhart and did more with that pick than the Bruins managed to do with any of theirs.

It comes down to who the Leafs would entertain trading, and acknowledging that Griffin Reinhart level fleecings are a rarity. Both Leo Komarov and James van Riemsdyk are capable of fetching a first round pick on their own, assuming the Leafs would considering moving one or both of the forwards who might play significant roles in their top six next season.

Beyond that there are players that the Leafs would love to move, but they are unlikely to earn a first round pick in return. Bozak, Laich, Michalek, and Bernier all likely have For Sale signs hanging around their necks, but injuries, age, and performance will make them challenging assets to move, and would essentially need to be turned into picks in order to flip picks to move up.

I’ve chosen to ignore Kadri, Rielly, and Gardiner in this, and with Kadri and Rielly receiving new contracts it’s probably reasonable to assume their safe. As for Gardiner, it remains to be seen if the Leafs love Gardiner as much as the internet does, but with defense being a huge weakness for the Leafs, it’s hard to imagine that they’d make it worse only for the chance that in 4 years that might have a defensman who plays half as well as Jake Gardiner.

Who’s Giving Up Picks?

That’s the kicker, while having an appetite for more first rounders seems normal, finding a team that is shopping theirs is much more rare.

Multiple Pick Holders

Along with the Leafs, the Bruins, Coyotes, Jets, and Hurricanes own two first round picks this year.

Boston: Given that the Bruins used all three of their first round picks last year to start preparing for rebooting their franchise, it seems reasonable that they’d do the same again this year. It’s safe to say that they whiffed on their opportunity last season and need to make it up for it this year, as such their 14th overall pick is probably not in play. The same probably can’t be said for their 29th/30th overall pick which may help the Bruins wind up being a bubble team on the right side of the bubble next year. It’s generally never a good thing when the Bruins and Leafs trade, but their need for affordable roster players and defense might make them a target.

Winnipeg: The Jets are one of the teams that can truly rival the Leafs for high end prospect depth, and breaking from that formula seems unlikely. In an era of No Trade and No Movement Clauses the Jets are as tough a sell for trades as they are for free agency and will need to always build through the draft. The second overall pick is definitely not going anywhere and the 22nd overall seems equally unlikely to move as the Jets have done well with picking up talent that shouldn’t have fallen that far in the draft.

Arizona: Maybe it’s because they have an analytics based GM that I assume the 7th and 20th overall picks are untouchable. You’d assume there’s an awareness of the value you need to get out of entry level contract players, and that’s multiplied with a cap floor team. That being said, it’s equally likely that Chayka is well aware that a player you select with a 20th overall pick is getting into crapshoot territory and might want to bet on a sure thing. Whether the Leafs have anything that would appeal to the Coyotes remains to be seen.

Carolina: Given Peter Karmanos’ current lawsuit, and the general up in the air feel of the franchise, it’s difficult to determine what direction the Canes will be going in. At 13th and 21st overall they have the opportunity to add two good, but maybe not stellar prospects, but that may be committing the team to a longer rebuild that the organization is comfortable with. With roster needs across the board, they can use these picks creatively to fill holes in the lineup or they can come away with two good prospects and try to bottom out next season to draft a bit higher.

Picks Available in the Top Ten

There are few of these picks that will become available, minus an extremely aggressive package for moving up in the draft. Using picks alone, it’s probably unlikely that Leafs can or would want to get it done. As for teams that would rather have a roster player than a pick, the only certainty is the Edmonton Oilers at fourth overall. It’s so much a certainty that TSN has the pick on their trade bait list.

Getting that pick for the Leafs seems like a virtual impossibility. Edmonton is wanting defense worth that pick, and in Toronto’s case that’s either Rielly or Gardiner, and arguably the Leafs shouldn’t be considering that. Add to that the Oilers are want a right handed shot, and preferably someone with size, you can probably rule the Leafs out of this option.

Beyond the Oilers at number 4, it seems reasonable to speculate that the Colorado Avalanche who are in a very similar situation to the Oilers might be willing to entertain doing something with the 10th overall. Having stockpiled a core that is reaching their mid 20s, it’s reasonable to assume that Colorado would make a deal that would add a piece to work with that group, but figuring who that player would be means climbing deeper inside the mind of Patrick Roy than anyone should feel comfortable doing.

Who’s #GoingForIt?

The rest of the pack is about trying to figure out who is motivated to make a leap a forward and give up a first to do it, and who on the Leafs could possibly get them to complete a trade.

New Jersey: Given Lamoriello’s ties to New Jersey it’s reasonable to consider them a potential trading partner. After seeing what can happen when riding a hot Cory Schneider through the season there might be some appetite to add roster players instead of prospects to the organization, and James van Riemsdyk is a relatively easy (lazy) dot to connect here.

Ottawa: The Senators are an absolute wild card and always will be as long as Melnyk is involved. The Sens have developed a decent young talent pool and might be inclined to take some chances again, but it seems unlikely that the Leafs have the piece they want. Like the Devils you could maybe consider van Riemsdyk because of his Sens friendly contract, though it’s their blueline that likely needs to be addressed.

Minnesota: Until now we haven’t really looked at cap relief as an asset, but with Wild it might be worth considering. Vanek is unlikely to live up to his $6.5M contract, and Komarov can be a cheap replacement for him at the cost of including their first. The Wild have one of the worst prospect pools in the league though, and might want to address it at some point.

New York Islanders: The draft has been Garth Snow’s bread and butter, but finding a winger for John Tavares is becoming as exhausting as finding a winger for Mats Sundin. I don’t doubt they’ll consider dealing this pick, especially since Snow will likely have fleeced the Oilers out of their 4th overall pick by now.

St. Louis: It’s Ken Hitchcock’s last ride and they have a lot of forwards that need replacing in order to stay competitive. I wouldn’t doubt that the Leafs could help them out in that area, although with the pick being as late as it is in the first it’s hard to find a Leaf that fits the need on their own without making the deal bigger.

Is This A Good Idea?

Honestly, I’m on the fence about it. This isn’t a stellar draft, it’s one that has three players who are lights out, a few others with some high potential, and a lot of really worthwhile swing or miss options that fill out the first four rounds. Having 8 picks in the top 120 and especially having 4 picks in the top 60 is goes a long way in addressing organizational depth without giving up assets for lottery tickets.

What it comes down to for the Leafs is what is in their best short and long term interests. Is it worth giving up on some older roster players because they can be replaced through free agency, and won’t be a part of the long term core? Yes, probably, but it’s a matter of where that line is drawn.

Both Jake Gardiner and James van Riemsdyk are likely for the Leafs to be players in acquiring additional first round picks, but are both around the age that they can still be a part of the new Leafs core too. In Gardiner’s case he is far too valuable to leave and the Leafs too thin on defense organizationally to believe he can be replaced anytime soon. James van Riemsdyk is a different story as depth on the wing is something Toronto has in abundance, although most of it is still unproven at the NHL level.

As much as I can talk myself into the fact that trading players like van Riemsdyk or Komarov is a good idea, there is still knowledge in the back of my head that ultimately the pick will never live up to player given up. A draft pick is nice, but a slightly more proven asset is better, and targeting already drafted prospects or young roster players is the more sensible option.

Sensible doesn’t really factor into June and July too much, when we’re ready to anoint Bryan Rust and Conor Sheary as future stars and trading proven NHL players for Luke Kunin seems like a good idea.

As for trading up, that’s really not something you can assess until in the moment on draft day, but the Leafs have shown to have a competent front office capable of assessing talent well. If they were to chose to move up, I’m comfortable with the fact it won’t be for someone like Tyler Biggs.


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