Alan Smithee said:
The final pieces that the Leafs will need aren't going to be an easy find. I think they are going to need the kind of luck that the Blackhawks had when they drafted their Norris winning, all-star defenseman Duncan Keith in the 2nd round. Of course, the Hawks would tell you that it was organisational superiority that led them to draft Keith. Maybe it was. Whatever it was, the Leafs need some of that.
I think the Leafs may be able to solve a few issues through trades, but they aren't deep enough yet to give up significant pieces to fill the biggest holes, unless they capitilize on another team's mistake. UFAs will factor in, but moreso when the team is really good.
Seems to me a major challenge is that the timing is lining up wrong. Chicago drafted Keith in 2002 and Toews and Kane in 2006 and 2007. I look at other contenders like Tampa and Pittsburgh they drafted their big defenders (Hedman, Letang) at about the same time as their big forwards and early in the process.
It's common knowledge that D-men take longer to mature, especially at the defensive aspects of the game. To be on Chicago's timeline we needed to draft our Keith 5 years ago which isn't happening...to be like Tampa/Pittsburgh it would need to happen very soon.
I guess one way out is a big UFA like Boston got with Chara but it seems like you need luck (or tax advantages that Toronto doesn't have) to pull that off. For example Shattenkirk, whether he could be the guy or not doesn't even matter when by most accounts already has a very short list and Toronto isn't on it.