I agree that the max will probably have to be the Giroux trade for the Leafs to even entertain the idea, but a 2023 1st + a 3rd wouldn't be like the Giroux trade.

Giroux+ 2 AHLers + a 5th were trade for Owen Tippett (former 10th OV pick but never did much yet prior to the trade) + 2023 3rd + 2024 conditional 1st (top 10 protected)

Tippett was a former 10th OV but never did much prior to the trade. I think maybe Robertson would be an okay replacement here, not as high of a pick but he hasn't been tried out as much. He is injured and is starting to build a history because of his style of play, but considering that Kane might be playing through a hip injury, that's a fair tradeoff.

For the picks, it should be a 2024 3rd and 2025 1st (top 10 protected) for the Leafs. Instead of sending a pick back, retention would be free, and perhaps Toronto pays a 3rd team for retention. Considering that Kane might be injured and Dubas not being too keen on moving firsts (specifically the 2023 1st) for a rental, it might have to be a conditional 2nd that could turn into a 1st.

The fact that Kane isn't in NY suggests to me that Davidson wanted more than a current 1st+a conditional 4th or 3rd. So, I'm kind of skeptical that this would happen unless Dubas is targeting Kane+McCabe and the two GMs can find a middle ground that is less than the the two high asks combined.

If Dubas gives up a 1st for a Kane, he would be an idiot. Either way, I think his hip issues may keep him from being dealt to TO.

I honestly don't even think Dubas wants the 1st rounder to be in 2025. He's learned from his Marleau mistake.

Marleau? He had to get him off the books.

You probably mean Foligno, and I would agree. I'm not even sure if Dubas was aware that Foligno was banged up, I think maybe he had just recovered from an injury. There are red flags with Kane, so if a trade happens it would likely require a condition that he plays X % of the games and perhaps that the Leafs even win the cup for them to get a 1st. If they don't land Meier, which there is a high probability imo, then maybe they do turn to Kane but yeah the price will have to be reasonable.

No I mean Marleau because that ended up being the #13 OA pick. No one has a crystal ball. Knowing that the Leafs will 26-32 this year is like having a bird in hand, BUT push it to 2025 and that's like seeing two in the bush hoping/praying. Doesn't matter how good a draft class supposedly is...that's too big a delta to gamble on.

Well the Leafs didn't have their 2019 1st which was the "current" one (the trade happened on the second day of the draft so guess the 2020 one was basically the current one at that point). So it was really about trading their most valuable 1st to get rid of his contract.

The reason I think Dubas won't trade the 2023 1st for a rental is because he probably wants to trade back again to increase his draft capital, and with the draft being deep, he has a higher chance of getting a 1st round talent in the second round. So pushing it to 2025, would be good for them, however, who knows how competitive the Leafs will be by then, so that's a plus for Chicago could be the 13th OV pick if they don't have Matthews.

Yeah. I've thought of that. Taking picks further down the road could be very lucrative for CHI. At the same time, if TOR wants protections, and somehow the pick gets moved to 2026 that pushes things off even further. I think to balance the risk with the timeline here, conditions could only be a max of top 2 protection MAYBE top 5.

I doubt the Leafs will go that far into the future with a condition like that just because they don't got any of their core other than Rielly signed long-term and he's really their only long-term contract. A lot of things could go wrong by then lol.

Perhaps the safest is to go with a 2024 conditional 1st (top 10 protected, if the Leafs win the Stanley Cup in 2023 and Kane plays X % of games, Chicago gets an option between TOR's 2023 and 2024 1st). Then the pick won't be too far (Leafs will have at least Tavares+Marner under contract in addition to Rielly) but also not the current one unless the trade pays off. Then add a player with some term/low cap hit like Lafferty. I think a lot of the risk balances out even if Kane goes out if Robertson or Holmberg is the prospect/young player going back the other way.

Maybe. I still think it takes a little more. But all of that definitely gets it into a good balance of risk.

Yeah likely, there are always those other stuff that GMs throw in for contract spots/retention. Here it might require a 3rd team to come in, and so I'm not going to even bother trying to figure out what that part might look like . Only easily movable guy for cap is Engvall. Kerfoot has a M-NTC that would need to be navigated, and he'll likely have to be flipped to a contender by the Leafs for an asset.

My biggest concern about a Kane trade is what number will he wear? I can't imagine him getting that number in Toronto or Boston (if he opens up to that).

I mean... if it's just for the rest of the season, I could see Nylander saying he'll switch if Kaner wants 88. I know it's happened in CHI a few times through the years and wasn't that big of a deal.

I think he might just feel pressured to and not actually want to but who knows? I think asking another star player to change for a few months would be weird though. Maybe management would take it from him anyways if he doesn't want to change. Holmberg wears his former 29, but maybe he'll switch to 92.

I'm sure it wouldn't be an abrasive conversation and they would get his thoughts on it before they made a move. I doubt Kane would really care anyway. "88" has become synonymous with Kane in the public eye, but he has always said it just kind of happened and there was nothing special or specific about picking that number, at least not at the time. He could be more attached to it now. But who knows.