So what I'm hearing you say, is Leafs failure in the playoffs the past 3 years is coming at a much higher opportunity cost and includes far reaching future ones then just an early disappointing playoff exit represents..
Leafs traded their 1st in 2019 for Muzzin, and 1st in 2020 to dump Marleau to free cap space when they signed Tavares to his $11 mil deal and traded their 1st in 2021 for rental Nick Foligno.
So Leafs fortifying for playoff runs against CBJ, Mon and TB has cost the Leafs at least 3 X 1st round picks (excluding all the other picks invested ie 2nd Giordano, 3rd X 2 for Campbell & Clifford etc etc).
Leafs are heavily mortgaging their future with each round #1 loss doubling down on present day costs, and sacrificing future impact at the same time with each early exit. A franchise ability to develop future NHLers is ZERO if you don't even make them.
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.. Eventually an organization pays a steep price down the road when you start missing all those 1st round level prospects from future build potentials, paying for past failures.
So I can see the logical reasoning behind this thread concept of lets trade active players off the roster that are failing year after year and try and attempt to recapture the damage the GM has done to the Leafs future in hopes that with the cap space recovered, you make better decisions and add players that can help you win and not contribute to the team losing. That is what I would expect a new someone else GM would do to help erase past mistakes and minimize the damage inflicted on the Leafs future. Since we aren't changing GMs then the current one is tasked with that job of trying to get rid of players he acquired in his failed Cup competitive team building attempts.