Shanny and Dubas have built a culture where losing is ok because they're learning. Where a "killer instinct", standing up for eachother, starting on time etc will all of a sudden click with this group. Where players "care deeply" apparently but get no results. Where someone like Mik can go above Keefe and complain about ice time and suggest a trade. Where it seems certain players get what they want (Jumbo getting a regular shift, and on the PP regardless of his play. Mitch remaining on the #1PP despite it being terrible etc).
They both need to go. Bring new people in who have no emotional ties to these players and won't coddle them. Losing is not ok. If you want to be traded - buh bye.
I don't think they've necessarily built a "losing" culture, but teams at different stages need different emphases. For last year, we clearly needed way more actually hard core pressure - not the "hey guys just relax" Jumbo Joe formula for success (hasn't worked for him either, despite him being an amazing HOF player for many years). The Leafs in fact should have guys like Marner and Matthews take a really good hard look at Thornton's career, and undertstand, truly GROK that they need to do the exact opposite of that for playoff success.
In the past, Montreal as an organisation along with their fans were so hard on their players, much more hard core than the Leafs, and while some scoffed at how they chased away some talent in doing so, I started to learn that this process actually culled the weak from the herd - if you couldn't cut it and left, well, that means you wouldn't have helped them to a cup anyways, so it was a net positive.
So long story short - I'd make it a serious organisation. Serious, as in tone, the expectations, the work ethic required, etc. Screw coddling, and if it made a star unhappy, so be it - sink or swim and be gone. It would take guts, and would have to implemented top down.
I have a feeling that under that kind of program, that
- Matthews would become unhappy, and would have to be dealt
- Marner would shape up and be better for it, along with Nylander
- the rest of the team would perform better
My two cents.