I remember Shanahan pontificating on how the Leafs young stars would all take hometown discounts to keep the core together. Good times.
Me thinks those young stars looked at Shannahans contract history and saw how many hometown discounts he gave as a player.
In hindsight Tavares being available to them may have been a bad thing in that they should have pursued a d-man instead. That said after signing Tavares they needed to identify that one of the other 3 had to go. Nylander being the obvious candidate, he even made it easy for them by holding out. he had great trade value at this time last fall. Until his play improves I would argue he has none right now.
Not sure how the Marner thing resolves, I expect they will get him signed but have 50% of their Cap tied up in 4 forwards. Then next season they are left with No Defense again and not much money to find one. he has spent most of his trade assets already to free up space (Marleau deal) or acquire short term solutions on D like Barrie.
Assuming they get Marner done for something around 10.5M, next year they will start the year with a Cap hit of 65.7M or about 16M in space plus whatever cap increase there is. They will have 10F 1D and 1G under contract. Even with a cap increase of 3m , that is 19M to pay at minimum 3F, 6D and a backup goalie. In 2 and 3 years respectively Anderson and Rielly will need substantial raises.
Long-term maybe a big F has to go, maybe it is Marner now. The went from young loaded with talent and potential to Cap hell without even winning a playoff round.