The turmoil around the Leafs this last year destroyed the value of almost all Leafs players.
Kessel had a year comparable to Getzlaf in 2011 where he had only 11 goals (coincidentally, also the year Carlyle got fired in Anaheim), or like the Sedins in 2013 where they both had 50 points or less (also when Torts went nuts and got fired).
All those players were at a tremendous low after those seasons, dealing with terrible coaches and a circus around them. All of them would have had incredibly low value at the end of those seasons (remember what people were saying about the Sedin contracts after that year?).
The only difference is that none of them were traded at that point other than Kessel.
Add to that: this off-season produced dramatic lows in all it's trades and it was a perfect storm against the Leafs.
If they held unto Kessel and had him produce the way that he can, under a competent coach who could find a way to keep the heat of Kessel to *some* extent, there's no question his perceived value would have shot up as well.
I see what you're saying..the possibility that his value could go up was there, but I think there are other things that also have to be considered.
1. Possibility that his value could have gone down further - Fact is, the thought that his value could go up is as much of a guess that his value could go down further. The 2nd half of last season was literally one of Kessel's worst ever - i'll give you that. But how do we know being in Toronto one more year would have drastically changed that? The expectations that this management team has, as well as Babcock, appears to be a lot higher then even previous regimes as far as the players go, so we don't truly know how Kessel might have reacted under that environment - I would say the mgmt would have a better understanding of that then us fans.
2. Cap availability/Team interest mid year - I think its a risk to assume that mid year there 'may' be more teams interested in Kessel and be willing to create space for him. It seemed Pitts right now was the only team that really made a serious offer, that was clear from what Shannahan said, teams kicked tires, but nobody made a serious offer. And if Pitts didn't fit Kessel now, they were heading in a different direction. Thats gotta put the question of whether teams really were interested in 7 years of Phil Kessel at 8 Mil.
3. Rebuild/Culture change - Would have been awfully odd of management to preach culture change and bring back the exact same core group of players after repeated failures. We needed to move on from Kessel so the organization could move on even if the return wasn't the greatest. And I for one, though not totally satisfied, don't think the return was the worst ever. We did come away with 2 1sts, a 2nd and a 3rd. Pretty much what we paid for Kessel when we got him (no logic in suggesting that the 2 1sts we gave up were Seguin and Hamilton as thats on Burke for misjudging the talent of where the leaf team was when the trade was made).
I know you're suggesting keeping Kessel to start the year was your preference, but ultimately all teams knew Leafs needed to move him at some point, so to me there's really no guarantee holding onto him would have changed what could have been returned.
Maybe we agree to disagree that this is something that could have waited, as I really don't know if thats true. But I do appreciate your explanation and think it certainly has logic (unlike some posters here with opposing views but complete lack of logic and hence makes for pointless back and forth).