Why would they not? You already said it the only thing Anderson is good at is stinking out the joint. Half of the buy out hit would be passed to the Habs anyways. So even if a team was originally willing to take a chance on Anderson doesn't mean they would be willing to be patient with him if things doesn't work out.
Just no reason for the Habs to expose themselves to that risk at the moment.
Because it hurts them more, teams (especially contending ones) will try to do everything before a buy out. Can you provide with some examples where a team gave up assets for a player, and then bought him out the very next year when the player was making something close to 2.75x2?
Like I said, they'd retain him further and flip him if it gets to that point, teams don't want to have dead cap space for no reason. There is no risk from the Habs here. I'm also not following your logic in your doomsday hypothetical scenario.
If the Habs buy out Anderson next year, they get stuck with 1.9/3.4/1.4/1.4 dead cap space for the next 4 years. If they retain 50% and trade him to another team and this other team buys him out next year, Habs will now be stuck with 0.95/1.7/0.7/0.7 dead cap space for the next 4 years instead.
There is zero risk for the Habs, it's only upside. Either they only have to retain 2.75x2, or they have a dead cap hit of 0.95/1.7/0.7/0.7 which is objectively better than buying him out on their own. No Anderson, money saved no matter the situation, and gained assets all for the cost of a retention slot when we have 2 more next year.
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