To TOR: Jack Skille + Corey Crawford (or one of the other young goalies)
Chicago would get a very good 25 year old 3rd line center in Stajan who has good face-off skills, has had a 55pt. season, and would be an excellent replacement for Pahlsson. Stajan can also move up to play 2nd line center fairly well, if the need arises.
Toronto would get two young players who would help fill the gaping holes in the organization's RW and G positions.
I would like to think that this proposal serves both teams' needs as Chicago needs some form of cap-relief and Toronto needs more quality prospects. If it isn't fair, please advise on how to make it so.
I think you're overvaluing Skille a little here. Stajan has proven he can put up 35+ pts atleast if given second line minutes or better. He is 25, and signed to a great contract. Skille on the other hand, has only played 24 games, and only shown potential to be a top 6 winger. Stajan this year is what Skille is projected to be. Therefore, no, the Leafs would not have to add to that trade, CHI would.