Trades make sense. Not bad! I could see it

Looks good to me, except doubt Thornton will come to TOR or of Van would b willing to retain on Tanev.

I think Van should absolutely be willing to retain on Tanev if it gets them a better return. The Canucks have gobs of cap space, so retaining for 2 years isn't a big deal.

Hamilton for Nylander is just a lateral move. And the Leafs might really need Nylander at centre next since they don't have centre prospects.

Don't understand how it's a lateral move when they're significantly improving on the blueline. And Nylander will probably be a fine center, but he's more likely a better RW for Matthews if he stays.

Don't know how you can think it isn't a lateral move in talent. Yes the Leafs get better on defence with Hamilton but they get worse at RW or possible centre. Even by this post where he Leafs sign 2 short term UFA centres and Gauthier are gone the by following year.
Not saying it's not a fair trade but like most trades, it helps in one position but hurts in another.

Nothing wrong with a lateral move if it addresses an area of need (Defence) and taking from an area of strength (wingers). But your point stands very true...if he's seen as a future C with the Leafs then it is no longer dealing from a position of strength.

That being said I'm not sold on Dougie being a guy I'd give up Nylander for.

Bennett could become a quality 2/3 center as well.