So what it sounds like for over the last 1/2 a decade now Matthews, Marner , Nylander with Rielly is 0-6 in round #1 results and Tavares has joined them for the past 4 for 0-4 when you have 4 forwards using 1/2 your Cap.
Then in 2 years with Rielly already locked in is to re-sign all of Matthews, Marner and Nyander to new contract raises, and JT takes a pay cut to help cut into those cap costs and the band is all coming back for the next 6-8 years using up 1/2 of the teams cap again with just the very same 4 forwards.
For this plan to succeed I'd suggest this group better find playoff success in the next 2 years between the ending and re-signing years of contracts as its unlikely our new GM by then without playoff success will be fully on board. IMO
At what point in time has the experiment failed, and that it is proven you can't win in a salary Cap world with only 4 forward using up 1/2 a team cap? I'd suggest the next 2 will be the deciding ones.
Our Leafs always have it backwards it should be WIN first and then Sign big contracts second, when the model is sussessful and proven it works with this core player personnel. Leafs plan seems to be how do we get these players re-signed and lets see if they can win together, and to this point there is no concrete playoff evidence that is can.