The sad thing is at the time we protected Holl, we didn't have one prospect that was ready to take bottom 3 minutes? That is an inditement on the Shannyplan. Again it was not a decision between Hallander/pick or Holl, it was a decision between Holl or McCann. Hallander and the pick were already out the door at the time Seattle made its pick.
Absolutely... but it wasn't that simple.
The Leafs could not afford to keep both Kerfoot & McCann. They liked what they had in Kerfoot, especially what he showed in the playoffs with Tavares out.
If Holl goes, then the Leafs are tasked with finding a #4 defenceman for the right side, with somewhere between $2m (McCann out, sign Ritchie) and $3.1m (Kerfoot out, spend $2m on a winger), with one of Kerfoot/McCann to use as bait.
If McCann goes in the XD, then the Leafs simply have the ~$2.5m they spent on Ritchie to find another LW.
Could it be proven to be the wrong decision? if Holl's poor play from the first 7 games of the year is a solid indication, then, yes, absolutely.... but for all the people ragging on the move (especially because McCann has started so well in Seattle), there haven't been a lot of suggestions of how the Leafs would replace Holl in their top 4 with the information available during the offseason.
There's also the consideration -- if Kerfoot is gone and McCann stays (which is a jusifiable move, I think McCann's a better winger than Kerfoot is, cheaper too) -- can you afford to make David Kampf the team's 3rd line C, knowing what that'll mean if either Tavares/Matthews get hurt. If somebody better is required, there is of course cap considerations there.