The fact that you got 3 10mil plus players on your roster is a pretty clear indication your team is in win now mode.
1. It shows your team got talents if not why have three of the top 10 salaries in the league.
2. Salaries might not reflect on players skill but it is an indication, having three of the top 30-40players in the league should means the team is in capable of winning now instead of 5 yrs down the line.
3. Having someone like Pietra, baring injuries, he should still be at his level for the next 3-5yrs. Are you saying the Leafs are rebuilding the next 3-5 yrs?
Also, once you sign those big contracts, as I said immediately after, "we are going to live and die by their ability to get it done, to find the will to win". It's been four years. You can't keep yourself handcuffed for 3 more spinning on the same wheel hoping one day they just turn the corner dramatically.
I'm not saying it can't be done with the right tinkering, but other teams know how to handle them. The back end is desperately light and the cap isn't moving. They need a big acquisition/trade and it won't be for more scoring, so why not get the absolute best available?
They need balance up front. This means less glitz on 3rd and 4th line, more grind, cycle and shutdown. It's cheaper, but you can find good value if you look hard enough. That won't be as difficult a task hopefully. Many of the parts already here.
In all the years of Leafs playoff success (years ago now), they did so with top notch D. Number One defenseman are rare, not every team has one. They come available as UFA's, you have to look at them if you need one.
Especially for a young team looking for strong, stable leadership, such as Muzzin brought.
One of Marner or Nylander should go to make space if they can sign Alex. I say Kappy with a reasonable contract could do well with some board battling teammates and be part of a 3rd line. You then make it up as you must, but having half your D above average to top of league class, makes life much easier.
One thing is clear. This isn't 2016, they have had a chance to show they can get it done, with different players, coaches and supporting cast. Eventually it's time to say, "hey, someone needs talented, speedy young point getters, we've got them."
Whether to pick up A.P (my preference) or try something less certain, we need the best D possible.
Get the #1 D man. Build from that massaged core for the next 3-4 years. That's the ultimate window, because the cap isn't moving. Get the best player available and move one that hasn't worked as planned.