Until the Leafs are eliminated, they are not dead yet (just mostly dead).
Matthews and Nylander will be on the final year of their current contracts next season. It will be interesting to see where Matthew's head is at when it comes time for the Leafs to talk to his agent about a possible extension. The money is not going to be an issue with the Leafs. If Matthews wants to stay and the Leafs want to keep him there be an issue working out a contract. But does Matthews want to stay in Toronto? And do the Leafs want to tie themselves to Matthews for 8 more years at over $100 million given his playoff performance?
It's going to be an interesting soap opera in Toronto over the next 14 months. And we likely don't yet know who will be navigating the Leafs from a front office perspective through this period.
By the way, Leafs draft picks as stands right now for the next 3 drafts?
2023 - 1st (Boston's), 5th and 6th
2024 - 1st, 3rd (Islanders), 4th, 5th, 5th (from Chicago), 6th, 7th, 7th (Ottawa)
2025 - 3rd, 5th, 5th (Chicago), 6th, 7th
The Leafs 2025 first round pick was traded to Chicago as part of the Jake McCabe trade. It's top 10 protected.
So not only does the potential next GM have to figure out what to do with their top 4's upcoming contracts, they also don't have a whole lot of draft capital to work with.