I'd "take back" Cheech on a try-out, meaning if Ottawa buys him out and he gets healthy in the summer and all that, invite him to camp and see if he can make the NHL club. If he can't make the NHL club DW will do him a favor and cut him and see if someone else might take a chance (since Cheech wants to play in the NHL, not AHL).
NHL Head Coaches are, by and large, vastly overrated, especially when correlating the success and failure of the team to coaching prowess. Todd McLellan is the epitome of this.
Jonathan Cheechoo at one time was one of the faces of the Sharks franchise and was always the type of player that was fun to watch, gave 100% effort and often times would give the fans their money's worth. To see Cheechoo fall this hard is just awful, I truly feel bad for the guy to be honest. If Cheechoo were to come back to the NHL, regardless of which team, that large contract (the big elephant in the room) would basically have to be paid off first.
The league minimum would probably the only way he could come back. As much as I would like to see him a Shark again, I doubt seriously that's going to ever happen. There may be a possibility with the L A Kings since Dean Lombardi is there. He's probably not going to be a marquee name again, but he may have some game left if he lands in the situation which is the best fit for him. If he's just going through the motions at this point, he may be losing interest and not be long for this game.
I certainly wish Cheechoo the best and hopefully he will be able to use the coming offseason to get his head right and figure out what he wants to do with his career. As far as the Sharks Captains skate each year, I would hope they would invite him to at least participate in it. He did enough for the Sharks franchise to have at least earned that honor...