Quoting: oilsince95
Like I said, each team has their perspective on prospects. If you think TO would not trade Nylander for Bouchard and a 1st, then this discussion doesn't even begin for Ken Holland. Simple as that. This is simply not the route the oil will take to attempt to add forward depth. NYR, Vegas and other cap strapped teams are way better trading partners if this is how you see a trade between TO and EDM unfolding.
Okay a couple of things here.
Edmonton is cap strapped, this is probably the biggest issue facing them. Couple that with a complete lack of depth on the wings and down the middle and on defence and goal and you have a massive problem that is so difficult to fix. Its a disaster and its going to take a long time to fix.
Step 1) They need to totally reconstruct their scouting (Which Holland is doing) and player development departments (perhaps the single biggest issue facing the team)
Step 2) Draft talent and build up a good prospect pool and develop those prospects into pros in a modern sense (Get rid of the old boys club mentality and any old school thinking)
Step 3) Move out all players over 25 who aren't on good contracts or don't fit in to the long term plan for the roster construction
Step 1 is easy enough to do if Holland has control over the team, whether that is the case or the old boys club still has sway is anyones guess.
Step 2 is massively important and takes patience and investment (Read about what Justin Brazeau is doing this summer with the Leafs, he's on an AHL contract but has full access to all the Leafs training facilities and lessons with Barb Underhill, he could be an asset that cost the Leafs essentially nothing to acquire and could be a huge add if his skating improves)
Step 3 is the hardest part of this issue, how do you move Lucic? He has the single worst contract in hockey and moving him will cost you dearly or you sit on him and have a player that hurts you on the ice and takes up way too much cap space that could go to players that have a much greater impact.
Edmonton should absolutely be targetting tweeners all over the league. Guys that are 2nd/3rd liners on good teams who could flourish with more opportunity with a bigger role they won't get in their situations. Kapanen is a great example of this, he will likely not get much time over a 3rd liner in TO unless people get injured and they have a replacement in Bracco so he can be obtained in a fair deal. He also could be a 30+ goal scorer if given the right opportunities and him flying around with McDavid would be a perfect opportunity. I would definitely see what kind of deal it would take to get him if I was Holland