Chris said:
If you go the full rebuild route, you presumably dump a lot of big salaries (somehow) - some combination of Phaneuf, Kessel, JVR, Bozak, etc. Then it doesn't matter so much what a guy like Santorelli is making because we will no longer be near the cap limit. And if you (management) think that Santorelli is a good guy to keep around, and he wants to be around for a rebuild (probably not), then you can sign him to a reasonable deal.
Whereas what I'm saying is that if the Leafs are rebuilding, which they absolutely should, then it's imperative that they maximize the assets currently on the roster in order to have as many picks/young players as possible. There is no point where in trading some combination of the guys you mention where they'll have "enough" picks so as they don't have to worry about adding more. There is no method of building a team that is fool proof and there is no point where a team has too many good young assets(and if there is, those are the easiest things to trade).
Even if someone were inclined to put a ton of stock in the idea that Santorelli's character or work ethic or whatever were really valuable in a rebuild then you can try to sign him in free agency or, by virtue of the cap space they should have, go after the best character guy available. For a player like Santorelli, being able to overpay by 500k or so on a short term deal could have real sway and give the Leafs their pick of whatever third liners they want in the offseason without sacrificing their ability to accumulate picks in a very deep draft.
I think what a lot of people like myself are really not going to accept is that whatever sort of benefit you might think "character" plays to a rebuilding team Santorelli's character is not so unique and valuable that it outweighs tangible assets.