And most of them I am sure won their rings before there were 30 teams. People need to be realistic with how much more competition there is these days. Montreal last won a Cup in 1993, and proceeded to implode after the incident with Patrick Roy. The odds of Montreal winning a championship in the next decade are very slim, as slim as any other team.
The problem with Toronto media is that they are mostly just a bunch of journalists with no actual hockey background who think they are experts at analyzing the game.