Not saying losing Barrie or Muzzin is going to help the team, what I am saying is a team that is currently a contender (or outside contender if you can't stomach that) and their core has an average age of under 25, they have a longer window than most. Winnipeg for example is a team that has a much shorter window since they have a lot of problem contracts and older players signed for term. Regardless of what they've done or how many cups they've won in the last 10 years, right now, they are a young up and coming team that has a exceptionally talented core of young players they are building around. That's the point here, that's what I found pleasantly surprising.

They might have zero bad contracts, but Rielly and maybe Andersen are their only great contracts compared to teams like Boston that don't have a tax advantage and yet somehow gets their players to take less to keep the team together. It's not a coincidence that the highest paid player in the conference finals was Brent Burns at $8m AAV and his team lost. Having the cap hits the Leafs do on their superstars makes it too hard to have depth on forward and defense.

Edit: technically Barrie is a great contract, but only because of the retained salary.

Exactly, and the leafs probably can’t afford one of Reilly/Andersen when their contracts are up.

Tax advantage = bonus money advantage.

Using last seasons playoffs as ammo is folly. It was an outlier year that made zero sense. There hasn't been an NHL team to win the cup with a player making over 10 million because the teams that have players making 10 million are either old guard teams on their way out of contention (LA, Chicago, or young teams with players still on the rise, TO, Edmonton, Buffalo) Players making this kind of money is happening now and its not going to stop. TO is just on the forefront of the new market, nothing is going to stop these young players from getting big money. So you adjust accordingly which is why you are going to see (already seeing) secondary players getting squeezed hard (unless you are looking at Vancouver, they still like overpaying depth players to play in the bottom 6).

TO's players who make the most, contribute the most and apart from Tavares, have yet to hit their prime years. When they are at their best, is when you can expect them to be winning more. They are still learning what it takes to be winners.

Why? Because its convenient to your want that the Leafs are in trouble? Why not trade Kapanen to make room? Or Kerfoot if need be? Perhaps Andersen is let go and a cheaper younger option is brought in? Maybe something else entirely happens? You are always so quick to say, "No, the Leafs can't do anything that works for them, their only option is losing trades, losing guys to FA and losing hockey in general.

I am sure you were among the people that at the beginning of this off season you knew with 100% certainty that the Leafs would have to trade Nylander or Marner and definitely would have to roll with the worst defence in the league because they couldn't move Marleau or Zaitsev. Dubas found a way and will get Marner signed eventually as well. I don't know what he'll do next season, much will depend on the progression of Sandin and Liljegren, both of who look like they'll be good NHLers down the road (Liljegren looks like he's good enough defensively already) either way, moves can be made and smart decisions will be made.

This whole, there is no chance anyone can do anything ever, is all based in your own desires to see a franchise fail. I get it, I used to be the same way for Ottawa but its a waste of energy.

Yeah it would be something special to make the playoffs 25 years in a row with the salary cap in place. I am not sure you'd ever want to do that again. Rebuilds are needed to reset every 10-12 seasons

Boston doesn't have a tax advantage over Toronto worth mentioning. If anything, Toronto has an advantage over Boston due to all the endorsement opportunities available to players there. Your tax argument works if we're talking about Tampa or Dallas.

Teams that won recently have almost all dealt with a struggling or injured player and managed to have depth to overcome. Toronto doesn't have that. If Rielly goes down, how far are they from Marincin or Harpur stepping in? If Matthews goes down again, who's the 2C now that Kadri is gone?

Rielly would be a big loss, no question there. Luckily, Barrie and Muzzin are here this year, and hopefully Liljegren and Sandin are closer than people think but Rielly's been pretty durable. Andersen would be a bigger concern. As for the forwards, they have Kerfoot and Nylander who can play centre as well. There are very few teams that can weather a significant injury up front like TO can. Marner gets hurt they have Kapanen and Nylander and Bracco who can likely all contribute enough to offset that injury. Tavares gets hurt they still have an elite #1 centre in Matthews. TO has depth unlike almost any other team in the NHL. At least up front anyways.