Yes, the Leafs can be a player....but they shouldn't. I think some team would foolishly offer more.

Ya I expect the same. I think it makes more sense to hold strong on the Robertson situation (he could be very valuable in a few years when they need cheap contracts contributing, specifically 2024-25), but I don't think it's necessarily a bad play to punt and go for it this year.

They can, and Chicago would only accept this if Kane only waived for Toronto as Kerfoot is a cap dump to Chicago, Engvall doesn't have much of any value, and Robertson is out for surgery and prior didn't look that good.

Nonetheless, the Leafs should focus on a top 6 LWer that is cheaper IMO.

Ya I think you're mostly right. Kerfoot would fetch at least a 2nd rounder if they wanted to flip him though (maybe more if they retain half his salary). Engvall wouldn't be a bad player to resign and flip next year. With more of an opportunity, I think his scoring could increase to maybe 50pts or so.

Robertson would be a risk, no doubt, and they will likely get a better prospect in another offer, but he does have the pedigree, just not enough evidence at the top level yet. He's still very young though and he's got a track record at every level below the NHL of scoring a TON.

If you look at it long term, it's more like Kane (50% retained) for
Robertson
2023 1st
2023 2nd (maybe + 3rd/4th)
Decent roster player for next year generating another 2nd or 3rd at the very least

Also it helps extend the rebuild a bit where some other trade options might speed it up which probably isn't the right play at this point.

My opinion is no matter what the leafs offer I doubt Kane would agree to Toronto... Only thing to draw him there is having a go with Matthews.

Toronto shouldn't pursue 1 year of Kane, unless he agrees to extend, then Leafs have a serious cap issue.

Similar to the other opinions here...They can, but shouldn't. TOR doesn't have too many issues putting the puck in the net. Are they #1...no, but they have high end talent. It's not like TOR is going to drop Marner to the #2 PP unit. TOR's defensive unit is also quite good. If I were TOR...I'd focus on a 2-way forward. Whether than be a dominant #3C or top 6 2-way LW or a Defensive RD...all good debates, but Kaner's not going to wave to be on the #2 PP. He's going to want to be a major contributor wherever he goes.

Pretty sure Leafs would run a 5-forward PP1 if this happened. Also, playing beside Matthews on a legit contender would probably sway Kaner pretty heavily. I agree with you that a 3C and/or 2LW would be great, but if they had Kane and waived a couple of the extras, they could fit that in there as well.

Kerfoot is not getting a 2nd rounder back at his cap hit; a 4th MIGHT be possible. Also, the Hawks don't have the retention slots nor should they be responsible for obtaining value from him which is why he is a cap dump to the Hawks. Kerfoot has sucked this year on a very good team with the opportunity to play in the top 6, he's not going to be scoring more on a way worse team without linemates that are better then him or only marginally better then him. If the Leafs perceive he holds value at his cap hit, then they should not be including in a package to a team that only sees him as negative value, and trade him separately.

Engvall is worth a 5th rounder if flipped...no way does he get a 2nd or 3rd...he has very little value for a $2.25M cap hit. He's also a UFA so there is no RFA status and the Hawks have very little need to try to sign him so no point to include him to the Hawks unless you are simply dumping cap.

Robertson is a okay prospect still, but he's not a lock for a NHL job yet IMO which is why he doesn't hold a ton of value prospect wise.

This is the reality of what you proposed at best....

Kane (50% retained) + 3rd rounder
for
late 1st
Robertson
4th rounder (Kerfoot)
5th rounder (Engvall)

Now this is the reality of the way the Hawks will view the package coming back from the Leafs...

1st
Robertson (good top 9 prospect)
$2.25M cap dump
$3.5M cap dump


That offer easily gets beat if Kane waives for more then the Leafs. Furthermore, I doubt he will waive for the Leafs or a Canadian team, and if he does, Oilers will probably be waived for as well.

Lastly, the Leafs need a top 6 LW preferably a two way guy. Unless they are confident Nylander will play the LW side and be just as productive, then the Leafs should acquire a LWer not Kane.

I think you're undervaluing Kerfoot and Engvall quite a bit, but you're completely entitled to do so.

I also doubt Kane agrees to go to a Canadian team, but the Leafs are far and away the best option there if he's chasing another cup.

In the end, my question of "should they?" is likely more important than the trade package anyways, and you've made some good points there. I don't think they consider it if it means they can't upgrade elsewhere as well.

I think you're missing the point of what their values, or lack thereof, are to a rebuilding team...Engvall and Kerfoot may have rental value to a contending team, but not to a team tanking. Is a misconception from a lot of Leafs fans on here. Try building a AGM trading Kerfoot or Engvall to a contending team, especially at Kerfoot's full cap hit, for a 2nd and watch the feedback you get from the more respected users here.