Quoting: ChiHawk
You can win with a high paid center and winger; Chicago did it with Toews and Kane 3 times, 2 of which when they were the highest paid players in the league. That said, they also had an unbelievable defense and goal tending along with one of the best two way wingers of all time in Hossa.
True, but look at CHI, they had huge high end salaries in Toews and Kane, but also Seabrook, Keith and Crawford, way different than 4 high paid forwards. PITTS had Malkin and crosby, but also Letang and Fleury, LA had Kopitar, Doughty and Quick.
Toronto's issue is all their high end is at forward. Between their big 3 at 10mil plus, they have only 3 guys between that and 1.6mil (and no rookie ELC) in Nylander 7mil, Kerfoot 3.5 and ritchie 2.5, thats a huge chasm.
Chicago while not winning the cup since have until the last year or two stayed competitive and played well into the playoffs, even when adding/having other big salaries like shaw, saad, hjalmarsson, etc... Chicago just got old and all 5 big salaries got old with them, but for many years they were able to add what they needed to stay competitive.
(Not saying Toronto isnt competitive, but the over reliance on essentially 8 of their 22 players is not making them better)