For the Pilons and Levin? I'd say Howdeshell covers one Pilon skill wise probably, but doesn't bring the rest of what they do which is their heart and sandpaper, but with Jacklin it isn't terrible value. Probably Howdeshell + Jacklin + 3rd 2019 + conditional pick (2-4th rounder dependent on scoring and how the soo does) but then you have to cover the loss of Levin, which would probably be 2 seconds + 3rd + 4th (using Nizhnikov deal as comparable value since Niz and him are so similar impact wise, with Levin having more room to breakout next year so 5th becomes 4th.) + conditional pick (Levin could very well still top ppg and I think he will so a 2nd if he puts up say 85+ points and a 3rd or 4th for PPG plus in 60 games)
So deal would be :
Pilons + Levin for Howdeshell + Jacklin + two 2nds + two 3rds + 4th + conditional + conditional
The reason Howdeshell and Jacklin can't cover the Pilons cost is strictly because they are the types of players that aren't really worth dealing unless you get a good overpayment strictly because of what they do for the team. Their role in Blake Murray's development has been under appreciated as he really came on once they were with him more. They also are two of our very few energy guys, and they are two of the few players that had casual fans coming to the arena which is also an understated piece when talking about deals. Finally I can't tel you how many times I heard young fans talking excitedly about the Pilons, as role models and such.
In regards to Levin you may disagree on the Nizhnikov comparable but I think it is the best comparable out there.
I would be willing to look at a deal or deals around this though:
Levin for 2nd + Joe Carroll/Cole MacKay* + LeGuerrier + 3rd + Conditional (4th for PPG)
Pilons for Howdeshell + 2nd + Conditional (3rd depending on season success)
The star is because I would prefer MacKay but I think Carroll is more reasonable but we could knock the conditional off for MacKay IMO.
However both deals for me would hinge on moving Candella for another D. If we could move Candella then I would be all over LeGuerrier who I think could fit the role we need on D right now.
Players I'd reasonably want off the Soo in order:
*a returning Hollowell - I'd trade both Pilons + 5th if we could move candella for Hollowell and
MacKay
LeGuerrier
Roth (not sure if the fit is there)
Joe Carroll
Jacklin
DeMeo
Howdeshell
Then again I could be TOTALLY OFF value wise
but these are my valuations as a wolves fan. And you've seen some of my trade valuations on leafs threads in the past.