To me, it was the perfect storm for this team. First Shanahan was hired to try and turn the franchise around, then he ended up hiring Dubas, who then later hired Keefe. All three of them started their new positions within the Leafs organization without ever having had done this type of thing before. And this certainly showed with how those contract negotiations went!
Dubas and Shanahan handcuffed the team when they gave into Matthews' and Marner's contract demands. In February of 2019, Matthews had just inked a US$58.17 million five year contract extension worth an average annual salary of $11.634 million, the largest contract ever given to a rookie coming off of his ELC. Marner's agent, Ferris, told Dubas that Marner was going to finish the season before signing any new contract. Dubas then stated publicly that they would be okay with that because, "When they're ready to sit down, we'll talk. He's going to be a Toronto Maple Leaf for a long time, regardless of HOW we have to come to that." I do not blame M&M for their contracts, that is all on Dubas and Shanahan.
Yes the pandemic threw a monkey wrench into their plans of giving these 4 forwards all that money thinking they would still have enough to make improvements in the other areas, but I don't believe this would have made a difference. As I have previously said, no other team have put that much of their cap into 4 forwards, while still being able to build a strong defense core along with good to solid goaltending.
The way I see it is management put these 3 core players on a pedestal, thus creating the "entitlement" that, Matthews and Marner in particular, have surrounded them all this time. I am looking forward to the new culture that Tre and Berube want to establish where it's all about the "team", rather than the core and everybody else. When every player feels they are making a contribution to the team, then having a team culture naturally follows. Also, when any player is not performing up to the coach's standards and gets benched or healthy scratched, that also goes a long way to all the players buying in. Whereas when the star players are never held accountable while the other players are, that has to create a division amongst the players.