I do see some parallels to my football team, Man United. United is on a 10 year run of failure in which they’ve had 8 managers and spent like ~1.5B on transfers. Unfortunately, the only way they can get players is by paying them above market wages. The most elite players won’t touch them, so they end up paying elite wages to second or third tier talents. With poor ownership, they also have struggled to set a direction meaning whichever new hotshot European manager or former star they bring in installs a new system, often requiring entirely new players. This obviously takes time, and the media is waiting to pounce on the previous players, the new signings, or the new manager. They seem to take pride in it. I think there were several instances where United could have gotten it right, but it takes probably 3-5 years of patience and investment in things other than second tier players (development, improving the player experience).
The big difference is Toronto has had Matthews and Marner, both top 5 at their position (along with Nylander and Tavares who are/have been top 10 during their contract) in the regular season, while United hasn’t had a world class player in his prime since Rooney (10+ years ago).
Toronto is in a rough spot. Marner must go, but they’ll regret it soon enough. They’ll be a lesser regular season team without him, and there’s no other player in FA who comes close to replacing him (will Ehlers, Boeser, or Granny even consider Toronto). Matthews may also need to go, but they’ll regret it. They can’t rebuild because they’ve traded their next three firsts. If they were to trade him, his NMC, injuries, cap, 3 year term, and playoff performance, mean he’ll have relatively few viable destinations.
The fastest path to relevancy is probably trading Matthews, but without him and Marner I don’t think it’s completely out of the realm of possibility that Philly or Boston end up enjoying a very high pick from Toronto. They more or less gave the Sharks Couture and gave vanishing Seguin/Hamilton for Kessel. You can’t give up McKenna/Dupont to a rival for f***ing Carlo or Laughton. With Knies, Tavares, Nylander, solid defense and good goaltending that shouldn’t happen, but the Islanders had Barzal, Nelson, Lee, Horvat, and better defense and goaltending and they’re picking #1. If you’re Toronto, you sure you want to tempt fate? Injuries can sink any team.
If he hadn’t been booed by the fans whenever touching the puck, it might be the lesser evil to resign Marnrt, but given his second round performance, I don’t think you can sell the fans on that.