Genuine question, would you rather have Chych at 4.6M for 3 years or Sandin at 1.4M for one more year then ~4M for 6+ years

Depends. If I want to win in the next 2 years I would want Chychrun, as he is the better player right now. Beyond that, I would prefer Sandin, as I think he has a very high ceiling, and could become just as good, if not better than Chychrun. But since the Leafs want to win now, the trade makes sense for them.

Hawks probably decline. The only reason they retain on McCabe this season is to get back a 2023 1st. And a 2023 3rd and Abruzzese for Domi half retained probably gets beat by another offer as well. Kerfoot and Holl are both cap dumps as far as Chicago is concerned. Without retention, they'll be difficult to move to any of the teams competing for playoffs spots. Most have very little cap space.

Hawks don't care about cap dumps or needing to retain to deal Kerfoot or Holl in later trades. The Hawks are one of the richest teams in the league, who have gone on record saying they are willing to take cap dumps from other teams.

If they retain $1 million on each Kerfoot and Holl, they can definitely get at least a 3rd round pick for each of them.

In your deal, Hawks are retaining on Domi and McCabe. How do they then retain on both Kerfoot and Holl? They only have one retention slot left. And what if Toews or Kane asks for a trade. Hawks will have to retain on them in any trade. Yes, they are willing to take on cap dumps provided the deals make sense for Chicago's rebuild. Hawks would take on Kerfoot and Holl if they get their asking price for McCabe and Domi.

I'm saying they could retain, I still think you can move both of them without the need to retain. I think you could still get a 3rd or 4th without the need for retention.

And i'm sure the deal could be done without retaining on one of Domi or McCabe, it was just a thought. How would you make the deal fair then?

The two picks the Hawks would want with retention on both McCabe and Domi as proposed in the trade are both in the AZ deal for Chych. The '23 1st and the '24 2nd. I'm not sure how to rework the deal without those two picks. I just don't think it gets done at all. Maybe Knies instead of Abruzzese? But I'm guessing that doesn't fly for the Leafs.

If Kerfoot and Holl are worth a 3rd or 4th with no retention, why wouldn't the Leafs just trade them and keep those picks? That seems like poor asset management.

The reason the Leafs wouldn't trade those players for picks themselves is it would leave a void in their lineup without a player to replace them (such as Domi & McCabe).

What if the trade was:

Max Domi (full price)
Jake McCabe ($2 million retained)

for

Nick Abruzzese
Justin Holl
Alexander Kerfoot
Nicholas Robertson
2023 3rd round pick (OTT)
2024 1st round pick (TOR)

and maybe even add the 2023 3rd round pick (TOR) as well if needed

LOL. I almost typed "don't add Robertson" in my last response. There's probably no one on this site who has less interest in Robertson than me. He's undersized, injury prone, and I think overrated. He's just another throw in in my opinion. He may pan out over time (I hope he proves me wrong) but I feel like he ends up being a career AHL'er. I actually think the smart move for Toronto would be to hang on to him and let him play next season for the Marlies to rehabilitate his value.

The offer with no retention on Domi, and Robertson and the other 2023 3rd added is probably fair value (Leafs fans will say it's a huge overpay). I'd make that trade. I'm just not sure if Hawks GM Kyle Davidson retains on McCabe without getting a '23 1st back. That's the only thing that might hang up this deal.

Great discussion! Appreciate your insights. Wish there was more of this on this site!

Thank you very much, glad to have the discussion and the feedback on my post

I disagree with the Leafs wanting to win now, they will always want to win - I think this team only continues to get better

CHI said they would take on cap dumps *FOR THE RIGHT PRICE*. They aren't just gonna take on peoples bad contracts for no reason. It has nothing to do with "being rich", it's a strategy for bringing more high end assets into the rebuild. All owners are rich, or else they wouldn't be owners, and all teams have to meet the cap floor or else they are penalized. Also, Teams can only have THREE retention slots. Domi and McCabe would be taking up two of them in this scenario. So, CHI would only be able to flip one of them, and that is only IF CHI doesn't already need those retention slots for guys like Toews and/or Kane, or any other trade with a better return than a 3rd and two cap dumps. That return simply isn't enough to warrant burning a retention slot. You might get Domi without retention for a 3rd and a prospect, though.