Tanev has 2 more years at 4.45M cap hit. With Leafs still needing to re-sign Matthews, Marner and Nylander and with Kadri and Rielly needing new contracts soon after i just don't see how we can even consider re-signing Tanev to an extension. We're probably gonna lose Gardiner to free agency because we won't be able to afford him. So when Tanev's current contract ends he'll be 30, having (to date) played 70 games once. Signing him to an extension is way too risky for a team like Toronto becuse that contract could turn horribly very quickly.
So now that we've established that, lets just look at Tanev as an addition to the team for the 2 seasons. Core players are off the table, and managment won't part with Liljegren, Johnsson and probably Sandin. Prospects like Bracco and Nielsen have little trade value, so lets look what we got? Durzi, 2nd round pick this season - would Dubas be willing to part with him? Grundstrom, Korshkov and Rasanen? Don't know how highly Dubas values these. Grundstrom was quite good in AHL so i suspect it's unlikely Dubas would move him unless for a defenceman that would join the team for more than 2 years. Besides that we don't really have much to offer, other than picks. Timashev i suspect is in the Bracco category, not much trade value and management hoping to develop them in nhl players so no point in moving them as they'll hardly entice anyone. Engvall in same territory, looked promising in AHL playofs but all teams have prospects like that. And then there's the roster players like Carrick, Rosen, Borgman (these two semi prospects but w/e), Leivo. Kapanen and Borwn, despite Brown being NHL for full 2 seasons, i figure are in same boat. If the management really wants to impove now they could offer them, no one would really cry. or maybe they see them as regulars and prefer to keep them. Only they know, us fans can only guess.