If he was looking out for himself and wanted a lucrative long term deal, why would he ever take a one-year deal?

Such a side-deal wouldn't be enforcible since it circumvents the salary cap. Nylander takes this offer, and then the Leafs can't afford to give him a q.o. next summer (which requires a 10% raise over his previous salary?) so he walks as a UFA, and after three years of keeping up with Matthews, gets at least 7x7 on the open market.

And then he gets hurt or has a bad year and the leafs say "what deal?, that would be illegal"

Fact is there is no handshake deal. Nylander could walk as UFA next season since the Leafs couldn't match his CBA regulated 12m deal. Plus this isn't cap workable for the Leafs. Leafs have to have no carryover bonuses into next year

If Nylander took a deal like that he'd be either a fool or a genius.

Fool: He takes it with intentions of getting less in the long term and plays a year where if he gets injured he is S.O.L.

Genius: Since it's non-enforceable, he doesn't do a deal and now Toronto either gives him his Qualifying offer which would be 13+M or they don't extend a qualifying offer and he becomes a UFA ready for big money.

Good points. I never thought about it like that. I was just thinking of the average over the combination of the 1 year deal and long term deal.