Outside perspective here, but the Leafs seem to feel pressured to make big dramatic gestures to appease the fanbase, and one of the consequences of that is that when these big, dramatic gestures don't go perfectly, and they never go perfectly, you get stuck with a lot of dead cap and immovable players.
As it is Toronto is not going to have a first round draft pick for awhile. It's way easier to say this for me since I'm not from the area, but it may be just time to pull back, keep the proverbial powder dry, and begin a restock of the farm system. I'm not an expert on the Leafs farm talent but from what little I do see the cupboard is pretty bare down there right now and that's a problem with a lot of existing gaps in the big-boy team to deal with..
I'm just saying, rather than bringing in more high priced free agents to make your roster crunch even worse it might be time to work the waiver wire, try to target high potential low cost talent from other teams and try to build broad instead of tall for awhile. Hell that's what my Bruins were doing last year and we fluked into a President's Trophy due to a lot of those guys plus homegrown talent gelling together out of nowhere.