The Puckpedia pick trade calculator gives you fantasy pick trades with it's find fair trades button (it gives you pick results involving picks the team in question doesn't have), but it does a nice job of displaying pick values once you enter the picks manually.

I'm using it to calculate potential pick swaps for the Leafs first-rounder. There are three broad types of pick trades with a late first-rounder. The radical approach is to trade right down into the second round and get back two picks that would be fairly close together in order. This is the kind of trade that sees late firsts and early seconds as fairly equally likely to get you a player of value and the trade gives you two shots at it. The Leafs attempts to do this in the past have had mixed results. It is gambling after all, if you think one roll of the dice is the proof of concept, you're not likely to ever be in favour of any pick trade. All have examples of failure.

This seems like a good year to consider some sort of drift down the draft order, just maybe not that far.

In particular, there’s very little separating the six players from No. 33 to No. 38 — Charlie Elick, Egor Surin, Nikita Artamonov, Dean Letourneau, Matvei Gridin and Jesse Pulkkinen — with those ranked from around No. 25 to 32.
Bob McKenzie’s Final NHL Draft Ranking: Many attractive and diverse options after Macklin Celebrini | TSN
This year’s final ranking, from No. 2 on, is much more challenging to assemble because of two factors - many more divergent opinions and variance on even the top 10 picks and two Russians forcing their way into the conversation in the upper echelon.

The less radical trade is to move down a few spots and pick up a later round pick to pay for the move. This is how the Leafs got Rasmus Sandin and Semyon Der-Arguchintsev out of their 25th overall pick.

The third type of trade is the reverse, where a team trades up. The opposite of the Sandin trade is St. Louis looking to get Dominik Bokk before someone else could take him. This didn't work out for them, but it is a common strategy for goalies, usually in later rounds. And for every trade down, someone has to want to move up. Sometimes teams without a first-round pick want to get one and will make that happen by cashing in some second- and third-rounders.

I'm going to focus mostly on the less radical trade down, because the big move to split the pick into two seconds is not something I can really see the Leafs doing right now.

Finding a trade

The calculator says the Leafs pick, the 23rd overall, is valued at 16.01. The first team I want to try to trade with is Carolina. They have the 27th overall, which this calculator shows to be worth 13.11. That means the Leafs could move down four places, and pick up an extra pick worth around 3. This calculator says a fair trade is the 67th, so the closest possible deal would be the Carolina 60th which is 3.58. The Leafs would actually be getting more than the value of their pick back, but teams can only trade the picks they have.

In the past, I've used other pick valuations, but this calculator one seems plausible enough. However, there is a difference between pick valuations in terms of probability of the future success of players taken and what teams actually do when they make pick trades. The only analysis of pick trades that seeks to set a market price is a little old, but I want to compare:

NHL draft: What does it cost to trade up?
A lot of work has been done on estimating the value of a draft pick. (For example, link, link, and link to links.) On Wednesday someone used this one (based on this one based on this one — seriously…

This method which looked several years of pick trades prior to 2012, has the 23rd valued at 19.5, the 27th at just under 17. The 60th is at 3.8. So this seems to indicate that GMs, at least back then, would have balked at that deal as far too tilted towards the Leafs.

What would the Carolina GM think, though? We can only imagine that, but it's worth asking why Carolina wants to move up here. This is always the issue with pick trades. The team paying two or three picks for one higher pick has to have a reason good enough to override the very good reasons to just have more picks in total. Maybe the Carolina GM is a guy who thinks about drafting more deeply than in terms of just having a better first-rounder and isn't the trade partner here.

What about the Flyers? They have the Panthers 32nd overall which is worth 10 in value on the Puckpedia scale. They have the 36th and the 51st, the 36th is too good and the 51st isn't good enough. There's no likely deal here.

The pick that's really worth grabbing, in my opinion, is the 33rd. The perception of value difference between the first pick in the second round and the one right before it is often shockingly vast. The first pick on day two of the draft is also a great pick to have because you have hours to choose between all the hundreds of available players left.

The 33rd belongs to the Sharks and is valued at 9.92, and if you add the Sharks 42nd overall, you get a total value of 16.68. That's a good deal for both sides, as Pierre LeBrun would say.

Why would the Sharks do this? Well, the Sharks have very bare cupboards, but do have two picks in the first round. The first overall and the 14th overall. They might just want to roll the dice once at 23 instead of twice at 33 and 42. They need players closer to NHL readiness, and they're making deals right now to get them, they may be trading that 14th.

Pick trades are often done in the specific context of the draft as it unfolds. So if a team is seeing and hearing that the player they want will be available a few notches down and another team is hearing their guy will be gone by the time they pick, that's when a match gets made. The Leafs need to be sure the player they want is going to be available a few spots lower. But more important, the other side of the deal needs that big motivation to move up.

Dallas might be a perfect match on desire, but they don't have a second pick worth enough to add to the deal. Montréal has the 26th and 57th, which is a bit of an overpay, but not much. Calgary has the 28th and the 62nd which is about perfect. It helps that both of those picks were received in trade because teams seem more willing to trade picks that aren't "theirs".

The Rangers can't make a deal, the Ducks can't really come up with a good combination either, and Ottawa traded the Bruins pick back to them. So it seems like the opportunities are pretty limited. Wait. the Bruins? Nevermind, their next pick is the 122nd, they're worse than the Leafs for poverty.

Would Calgary do a deal with the Leafs? There's rumblings that there is "politics" there that's keeping the relationship sour. I can see that. Brad Treliving quit over the coach choice, and then the Flames upper management had to admit he was right and fire Darryl Sutter. No one ever likes the guy who turns out to have been right. And the Flames did make a big deal out of Treliving not participating in the draft for the Leafs – who then promptly drafted a guy linked to all the pre-existing scouts and Leafs-adjacent people and made their concerns seem absurd.

It would be fun, though to get that extra Flames pick and grab a winner with it. I honestly think Montréal is the most likely trade partner – although no pick trade is the odds on favourite to my eyes. The new Habs brain trust like to get their man and be seen to do it. It's a kind of performative decisiveness, which makes them more likely to move up than most teams.

Enjoy the pick trades. Once the de-centralized draft comes to pass, these rapid-response deals will likely disappear. But look on the bright side, if someone is going to make a bad deal it's likely to be in Vegas.