Leafs likely accept but klingberg is supposed to be on ltir all season

I'd be shocked if the Sharks use their last retention slot on anything other than rentals for the next few years. Also, in this scenario we'd be tying it up for 4 years for a bottom six player, a 3rd (after the Grzelcyk trade), a 5th and a 7th.

Just looking at this season, if Hoffman keeps getting his game back we could use it on a trade with him and probably get a 3rd back easy (without the slot his cap hit is probably not tradeable). There are plenty of other realistic trade scenarios too where teams will pay a premium to squeeze someone under their cap. Salary retention could easily be the difference between a 2nd and 1st in some trades. Multiply that by the next three seasons too and you can see how much of a waste it would be for SJ to tie up that valuable slot.

This deal doesn't come close to paying for 4 years of retention (let alone the $16m) and that doesn't even account for Couture's value, however low you think that might be.

There is limited reason for San Jose to trade Couture. They have to normalize his salary for the acquiring team and that limits what they can do with another player. Couture is worth the leadership. Hes a bad contract, but it’s not like San Jose has cap issues and they will have to overpay to get vets to come anyway.

You are never going to get the return necessary. That slot probably ties to a 3rd round pick for Duclair.