After looking at last year’s trades of picks and players, it is obvious that most pick trades are fair.  Broad Street confirmed this on a larger scale and in a more rigorous way and published their results in 2013:

By this approximation, three out of every four trades were roughly fair, meaning that the two teams’ packages were within 20 percent of each other in estimated value. Moreover, almost all of the ones that were off by more were very minor moves, where being off by 30 or 40 percent still isn’t very much in absolute value. Two 6th round picks are probably worth a lot more than a 5th, but I doubt the Flames are losing sleep that they might have given up too much when they made that trade in 2007.

So assuming there is not actually anyone out there who does not understand the value of their picks in a meaningful way, what can the Leafs legitimately do just in terms of pick swapping?

Revisiting Last Year’s Pre-Draft Trades
Revisiting Last Year’s Draft Day Trades

The Assets at Their Disposal

To keep this from getting loopy, I’m sticking to 2018 and 2019 picks. Teams do trade farther into the future than that, but not for anything put low-level picks, usually.

The 2018 picks are:

  • 25
  • 52
  • 83
  • 118
  • 149
  • 209
  • 211/

The 2019 picks are, well, we don’t know. Let’s use the alphabet draft order like Cap Friendly does, and just accept it’s an approximation:

  • 27
  • 58
  • 89
  • 118
  • 120
  • 151
  • 182
  • 213/

The only one not the Leafs’ own pick is the 118th, so this is likely a decent approximation of expected value in a trading partner’s mind.

Trading the 2018 First


Up or down? Let’s start with down. There’s only a couple of likely trading partners. I’m using the same valuation system I used before, and it has the 25th at about 18 points.

If you want to get two second round picks out of that to double your chances at getting a player, you need one team with two seconds that work out to about 18 points.

Detroit has the 33rd and the 36th, which add up to about 10.5 + 11 = 21.5. This would be great! But Detroit would need to really want the guy coming up at 25th overall.

Montréal has the 35th and the 38th and that is about 11.3 + 9.5 = 20.8. This is much more likely, but again, what’s in it for Montréal, with no prospects in their system, to move up and have one instead of two? They’d need to have their eye on someone.

The Islanders have the 41st and the 43rd, and that is about 8.5 + 7 or 15.5, and that’s not enough; we’ve dropped out of the range where this works for the Leafs unless the rights to John Tavares are coming back too.

St. Louis has the 29th and the 45th, and if they just wanted to hop up a few to get someone in particular, that works out to 14.5 + 7.2 = 21.7 which would need a very motivated buyer, but would be ideal for the seller.

Of course, someone might be able to add their 2019 second to their 2018 to make this deal. Imagine we think the team we’re trading with will finish in about the same spot next year as this, nine points is the 40th overall, and that would make the Oilers the ideal partner.

Funny, isn’t it, that sounds like not enough, doesn’t it? But that’s the fair deal here.


Trading up is a different story, because now I’m asking how far? I think people imagine getting a top ten pick or something, and having a fun draft pick to get excited over. Let’s try it, see if it’s possible.

First, let’s go for the 11th, because the Islanders own it and the 12th, and they’re more likely to trade one than the Oilers at 10th or the Rangers at ninth.

You need almost 35 points to get the 11th pick, and we’re beginning with 18, so we have to find 17 more. I think you see the obvious way to do this. To get that pick requires the Leafs’ first this year and next. Is that worth it?

What if you add this year’s second and then some third pick to make up the value?

The 2018 second is 52nd overall, and it is worth about 5 points, so this deal is now short 12 points, and that means we need to add a much better second or a whole cascading pile of picks, and Lou is laughing at us. The Leafs would need to add a player to make their 25th and 52nd turn into that 11th.

This is less fun now, go away, Lou. We’ll go for a lower first than 11th, but still better than ours. The Flyers have the 14th and the 19th. Let’s go for their 19th.

It’s worth about 23 points, and we only need to add five to get to that with our first and that’s our 52nd! Hey, Flyers, make this deal, and we’ll have a marginally better pick and no second-rounder while you get two picks! Do we like that plan? It would need to be for a player we think is worth the loss of two chances at getting a good NHLer. Someone who has fallen, but might not fall any farther.

What if we only want to move up a touch, so we put the 25th with the 89th and keep our second. That’s 18 points plus, uh, 1.5. Huh. So what’s 19.5 or so get you? 23rd overall. That’s the Ducks, who don’t seem like the more picks are better type. Ottawa has the 22nd, and if any team was ever desperate for more stuff that’s free, it’s them. They might go for the deal.

Are we excited by this deal? For the right prospect, I guess, but I liked the trade down deals with Detroit or Montréal better if they are motivated buyers. Two picks in the 35-45 range are at 35-40 per cent chance of playing 100 NHL games (by Scott Cullen’s chart). But that’s times two (not exactly, but the cumulative probability is more than 60 per cent.). A 25th overall is about 54 per cent.

Now here’s a question to ponder: What would the Leafs have to add to their two firsts, this year’s and next, to get the Canucks to part with the seventh, which is the only high first that is even remotely likely to move? That’s 43 points worth of pick and we have about 36 points worth of firsts. Would they like to do that deal plus the prospect everyone is always willing to trade, Jeremy Bracco? Would you do that deal?

How much do you like Adam Boqvist or Noah Dobson or whichever player is available at seventh?

Vancouver reportedly wants an NHL-ready player now worth that pick, so they don’t even want this deal, but it drives home what a big trade up really costs.

Now how about trying for the Hab’s third overall, what do you want to offer for that...


I’m not a fan of trading up most of the time. In the abstract, it’s always a deal that’s bad. In the specific case of paying two picks for one player — because that’s what you’re doing — it can be worth it. In the rundown of last year’s trades, there were some examples of really good moves up — not the goalie moves, necessarily, those seem rash for the most part — but Chicago going for Tim Soderlund or the Sharks getting that guy only they knew was good who is already in the AHL being good were worth it.

Those were both deep in the draft trades though. Where it all gets questionable is trading up in the first round. One thing that we can learn over and over in drafts is that players fall on draft day sometimes for no good reason other than other teams take someone else they rate higher.

Trading up in the high first round is easier for the aspirational team. There’s a lot of talk that Montréal should trade down to get who they want and get something out of it. And most people mean a couple of spots, not to where the Leafs are picking.

But imagine you’re Montréal. You have to do that deal before your pick comes up and then hope the player you want isn’t gone. It’s a much higher risk move than moving up right at the point you know who you can take. To do it, you need really good intel on what the other teams between your current pick and the one you’re trading for will do.

There are very good reasons why no one ever trades those high picks. And likely we won’t see any of them move for anything but players.

As for the Leafs? A player deal is safer, but the value of that pick is not high. You need someone who sees the value in just having a “first”. Calgary springs instantly to mind. But all the fantasy trades for Dougie Hamilton seem terribly implausible. Vegas doesn’t have a first round pick either, but they also don’t seem as willing to make trades for the sake of making a deal as the Flames do.

Should the Leafs trade up or down?

Sideways for a player.322
Don’t trade, pick a guy.1115