What a lot of people who fondly remember that era of Leafs hockey and constantly whine about not getting back to it completely forget is that there was no salary cap at that time. Which meant that if the Leafs needed an all-star goalie, they could go out and spent $8 million on Curtis Joseph. Now? Even if they weren't paying the Big 4 the money they are, they'd be hard-pressed to fit such a contract in without having to skimp somewhere else, which is the entire point of the salary cap setup in the first place. Teams that are rewarded in the salary cap era tend to be teams that have a handful of players emerge from literally nowhere to become key components of a Cup team. Either players take a few years to break out (see Nathan Mackinnon) and their teams are able to sign them way under market rate for a while, or they have a few guys from the minors emerge from nowhere (Tampa has benefited from this over their recent Cup runs, with guys like Palat, Johnson, Kucherov, Cirelli, Cernak, and on and on). The Leafs haven't benefited from the latter pretty much at all, and their stars emerged too fast for them to take advantage of the former.
If you had the choice between Tavares and Kadri now, which one would you take? And the answer to that question was an even bigger joke at the beginning of Tavares' contract.