The Toronto Maple Leafs have traded down in the first round three times in five drafts since hiring Kyle Dubas. It started out with the Nashville Predators 2015 1st round pick, which the Leafs parlayed into @Travis Dermott, Jeremy Bracco, and Martins Dzierkals. Then in 2018 the Leafs slid down from 25 to 29 to select @Rasmus Sandin, and picked up Semyon Der-Arguchintsev along the way.

The 2018 trade made it clear to me that trading down is part of Dubas’ modus operandi, some other teams would see the risk of missing out on their player and decide a mid 3rd round pick is not worth it. While Dubas likely already knew Sandin would still be there, he was smart to find a team desperate enough to move up and add another prospect to the pool.

If there is a winger available at 15 that teams are eager to bid for, the Leafs could get a much bigger return for sliding down from the middle of the first round compared to the late 20’s. I wrote not too long ago about the average surplus value of a draft day swap, and the most comparable trade would be the Flyers moving from 11 to 14 so the Coyotes could get Soderstrom. Philadelphia gained the 45th overall pick in that swap, and re-packaged it to move up to 34 and select Bobby Brink.

If the Leafs have their eye on a player but feel they can fall back a few picks and still get him, they have proven in the past that they will trade back to maximize their value. So who could they trade back with?

The Devils have three first round picks in this draft, including picks 18 and 20. If they feel like they are going to just miss out on a player, the Leafs offer a slightly better position. The drawback is that the Devils do not have a 2nd round pick, and the third they have originally belonged to Carolina (84th).

This means that if the Devils desire to move up, the most likely package would be 15 for 18 and 84. This represents an increase of 9.2% on the value of the 15th overall pick for the Leafs. I don’t see why the Devils would place much more value in moving up from 20 instead of 18, but at that point the move wouldn’t be worthwhile for the Leafs.

There is another option, but it is much less likely. If the Devils want to spread out their picks more they could swap 18 and 20 for 15 and the Leafs 2nd (44). This would allow the Leafs to select twice in the first round, while also increasing the value of their picks by 5.7%

I should note that the Devils have not traded up once in the past 6 drafts, while moving down 4 times in the same span.

The Flames sit at 19, with their own 2nd round pick (50th) as ammunition for moving up. It’s worth noting that the 49th overall pick belongs to the Arizona Coyotes, but they must forfeit that pick as punishment for testing draft-eligible prospects early. Essentially this will move every pick after 49 up one, but I’ve kept the original pick numbers for the sake of simplicity.

There is not a clear reason why Calgary would be motivated to move up in the draft, but it doesn’t always take clear motivation to complete a draft day swap. It can be as simple as a player they like falling to 15, and the Flames have the right picks to get a deal done. 15 for 19 and 50 would be a 21.6% increase in value for the Leafs, and they can try to find gold in the 50-60 range of the draft as they did in 2019.

Calgary has moved up only once in the past 6 drafts, trading picks 76 and 82 to select @Oliver Kylington 60th overall in 2015.

After the Flames pick at 19, every team in the 20-26 range is missing a 2nd or 3rd or both. Then there is Anaheim at 27 with Boston’s pick, plus they have their own picks in the first three rounds. At this point the Leafs are moving back 10+ picks in the first round, and a late 2nd round pick simply does not make up the value.

Fortunately Anaheim’s 2nd is 36th overall, the players available there could make it worthwhile to drop 10 picks in the first round. The value chart says 27 and 36 is not enough for 15th overall, so Anaheim would need to include their 3rd (67th) or Nashville’s 4th (104). Three for one swaps are uncommon but not unheard of, being done twice over the past 6 drafts. That is an improvement of 21.0% or 11.2%, depending on the latest pick.

Even though the pick values line up, Anaheim hasn’t made a single draft day swap over the past 6 drafts. It seems unlikely they will swap 3 picks for 1 in a season where they missed the playoffs and ended up with just 7 picks.

This is a team with an interesting supply of draft picks, and an even more interesting affinity for draft day swaps. The Sharks are tied with Arizona for the most swaps over the past 6 drafts (8). If you read my earlier article on draft day swaps, you would know they are not afraid to move up if they have a player in mind.

They do not have their own first round draft pick, but they do have Tampa Bay’s from the @Barclay Goodrow trade. If Tampa does not advance to the Stanley Cup Finals, their pick will be 29th. If they win the Stanley cup this pick will be 31st, if they lose in the cup final it will be 30th. The Sharks also have two 2nd round picks, 34th and 55th overall. After that they have no picks until the 5th round, 126th overall.

Since the Sharks have an extra pick in both the 2nd and 5th, I could see 15 for 29/30/31, 34, and 126. This would allow San Jose to consolidate their extra picks into one potential franchise changer, something it seems they are in need of. It would improve on the value of the 15th pick by approximately 6.2% and move the Leafs back to a position where they have found players like Dermott, Sandin, and @Egor Korshkov, with two picks in hand. It also adds to the litany of picks the Leafs have in the late rounds.

In my opinion there is a clear top 10 skaters in this draft (9F/1D) plus one goalie, and after that the value drops off. There will still be some incredible players at 15, and at least one of those top 11 will struggle in the NHL, but with what we know now the Leafs should increase the price significantly if one of them slides to 15.

The Leafs might even see a player like Rodion Amirov or Jake Sanderson as a top 10 talent and make the pick at 15, like they did with Timothy Liljegren at 17 in 2017. If they do so, it will be a player that they expect to contribute on an ELC before @Auston Matthews and @William Nylander’s current contracts expire in 2024.

If everyone is holding their breath for a player like Braden Schneider at 15, my opinion is that the Leafs would be better off taking a marginal win in a trade down. There is still a chance Schneider is there at 18 or 19, and there will still be comparable defencemen available at 30 or 31. I don’t think any Leafs fan would complain if they got a sturdy defenceman along the lines of William Wallinder or Helge Grans at the end of the 1st, then picked up a high ceiling D like Emil Andrae or Topi Niemela in the early 2nd.

Of course this is all dependent on the willingness of another team to trade up, and it is rare to see picks as high as 15 swapped. I believe that is an issue of supply rather than demand though, if the Leafs made the pick available they would likely have suitors. Draft day swaps are becoming increasingly common, and the approaching expansion draft will put an added focus on players that can step into the NHL right away. If a team sees a player they believe in like Arizona did with @Jakob Chychrun in 2016, they could be motivated to pull the trigger on a swap.

Overall I would still say it’s unlikely the Leafs trade down from 15, as they could also trade the pick for immediate help on defence. If they were to trade down, these are the 4 most realistic targets in my opinion. The Leafs would be wise to take advantage of the difference between the actual and perceived value of the 15th overall pick, depending on who is available there. Selfishly, I would also find great joy in another complexity being added to the already immense Kessel trade.

October 6th, 2020 is the first day of the NHL entry draft, where we will have our first opportunity to see more draft day swaps.