Quoting: justaBoss
The idea is that because of those never-ending huge long-term contracts they're forced to suck most likely the whole decade. They can't make key acquisitions to fill their weaknesses, while the team core itself is getting older and older. And worse. Moving some of these obstacles is costly, but it supports further their rebuilding. The worst possible scenario is the one where because of these contracts they are unable to re-sign players like Hertl and Meier, which is a realistic possibility, all things considered.
Perhaps without these contracts they could have a new, younger core to roll with as early as 2024-25. It's a long process, but considerably better than rebuilding piece by piece until they finally might make the playoffs by 2028 or something, after all these contracts have expired.
You wont have a new young core by 2024 if you have to trade first round picks to move guys. The only thing Wilson can do is be patient find a goaltender and yes I agree he will have to trade whatever he can to get prospects and picks to fill in around the large contracts. I don't get to see a lot of Sharks games but from what I've seen Burns, Ferraro, Karlsson, and Knyzhov aren't amazing but they work. Vlasic should play against slower teams and Simik the others as the 3rd pair. That means the Sharks should look for a better right side 3rd pair defenseman to pair with them, probably one who can skate. Merkley needs more time, so not him. If the Sharks found a coach who would install a sound defensive structure that could help as well.
Guys that Sharks should look to move
Hertl- he should bring a good return.
Meier- another nice return
Labanc- depending on the return
Kane? Not sure on his current value but if you can't get much just hold him.
Donato he should fetch a pick.
Jones you buyout after this year.
Obviously you expose any large contract you can to the Kraken but I doubt they take them for free.