Except that every single contract negotiation involves measuring past performance to determine future pay. It's not hard to understand someone questioning what have these guys done to earn these huge paydays.
Some contracts end up being very good value, others turn out to be horrible. It's natural for fans to anticipate how some will turn out.
Except through a lot of this thread people are trying to use the success that teams LA + Chicago HAVE HAD as the models of success 2, 3 or even 4+ year from now.
However, their is absolutely no proof that you can win with:
Chicago: Toews + Kane making 10.5 million each instead of 6.3 million. These guys making that much will mean less star power moving forward whether it be a Sharp or Hossa or Seabrook which will hurt them.
LA: Mike Richards who was a great deal but is now looking like the next player who falls off in his early 30s like Horcoff or Darcy Tucker did. Brown was making 3.175 per year but turning 30 this fall will be starting year 1 of an 8 year deal that pays him 5.875 per year. No Leaf would be happy paying him that.
The Leafs aren't in nearly as bad a shape as some fans want to make us out to be. We've got some very good young talent that can be front line players that has yet to fully put it together in Gardiner, Rielly, Nylander and even Kadri depending on how you want to view him.
The biggest issue I see with the Leafs compared to other teams that turned it around is that we haven't added a few top end talents (assets) at the draft in a cluster of only a few years. Adding Rielly was great by then following it with Gauthier the next draft was weak. When LA or Chicago were rebuilding they were fortunate (in the long term) to suck just that little bit extra to load up on more premium assets after they already had some other strong foundation pieces in place:
LA added Doughty, Voynov, Schenn (later was the main piece for Richards) in back to back drafts after already have guys like Kopitar, Brown in their system.
Chicago added Toews + Kane in back to back drafts after already having guys like Keith, Seabrook, etc. in their system.
Boston got Kessel at 5th overall then got very fortunate with getting Lucic + Marchand in the same draft after already drafting Bergeron + Krejci a few years prior.
Tanking so we can follow up the nice Nylander pick with another top pick or just getting really lucky at the draft is what this team needs if it ever hopes to be more then an average team. Even if we use the pick as a trade chip. Tanking would also mean we trade out some rentals for other extra picks. Toronto as much as anything right now just needs to be loading up on assets which is what they should have been doing in recent seasons instead of dealing for a guy like Bolland and eventually letting guys like Grabo, Kulemin, CMac walk for nothing. It was absolutely terrible asset management losing (or not gaining) longer term assets for these players in non-contending years.
Moving forward though with the exception of Clarkson our contract situation isn't bad at all. When teams like LA or Chicago were growing into elite team lets not forget that guy like Handzus, Smyth, Samsanov, Gagne were among their highest paid players.