Posted this in the thread on the main boards... may be a useful perspective here.
If you're the Leafs, perhaps you look at this deal from the perspective of summer 2017. If we assume no further moves happen with the pieces acquired, the deal is essentially:
Dion Phaneuf, recently turned 32, with 4 years left on his deal at $7m.
for
Tobias Lindberg
A 2nd Round Pick in the upcoming draft
The RFA rights to Jared Cowen with a $4.5m qualifying offer.
There are circumstances under which I'd gladly make that deal (namely if we can add a high end young defenceman with size prior to), and circumstances which I wouldn't (unable to procure any high end defencemen).
This trade screams cart before horse to some degree, but also could be viewed as a bet on the Leafs ability to get that high end defenceman. Between Kadri/JvR/Komarov/Bozak/Marner/Nylander/Kapanen/Leivo/Brown/Lindberg, if they draft a forward with their #1 pick this year, they've likely got the group up front they need to be successful.
The question is, can they convert some of the expendable assets, and perhaps 1 or 2 of those guys, into somebody that can compliment Gardiner & Rielly in a solid top 4, on a timeline which fits with all those forwards (realizing that the draft basically isn't an option as defencemen take longer).
Anything they get out of Michalek and/or Cowen, a theoretical bonus to that.