With the Leafs set to embark on a full-scale rebuild, the most pressing question among Toronto fans is simple: How long until the Leafs can contend.

Re-building is not for the faint of heart. It takes plenty of years of being utterly terrible before the first signs of tangible progress, and sometimes plenty more after that before reaching the ultimate prize (just ask the St. Louis Blues).

To get a better understanding of just how long a rebuild might take in Toronto I looked at three of the past four Stanley Cup winners to see how they did it. I excluded the Boston Bruins because they didn't really rebuild, they succeeded in pulling off the magical re-tool on the fly, in large part because they made the greatest free agent singing ever (Zdeno Chara) and lucked into two franchise goalies (in one case the luck was having a team as stupid as the Leafs to trade with). Basically, the Bruins model is not easily replicable.

For the Kings, Blackhawks, and Penguins, I defined the start of the rebuild as the first season in which they flamed out after having been in the playoffs or at least in playoff contention for a number of years. If you're in the playoffs or at least close enough to have a shot late in the season (as the Kings were from 2003-2005) you aren't rebuilding. It's not until a team drops dramatically in the standings that they typically commit to a full rebuild.

So how did they do it?

With the Leafs mired in another death spiral, the core is coming under increased scrutiny. The major question in Toronto is whether you can win with Phil Kessel and Dion Phaneuf.

It's certainly possible. And you have to look no further than the team who has won two of the last five Stanley Cups.

Dave Nonis forgot one last Christmas present under the tree for Leafs fans, and delivered it on Tuesday, firing head coach Randy Carlyle.

The move comes half a season and one contract extension too late, but the news of Carlyle's dismissal is positive nonetheless.

"Does it hurt to watch Tyler Seguin?"

That's a common question many Leafs fans get, especially as Seguin launches an offensive assault on the league.

You may have heard this before, but the Maple Leafs traded the draft pick that eventually became Seguin. The Phil Kessel trade is rarely discussed so don't feel bad if you didn't know this fact. Oh, what's that? You've heard that before. Of course, because by law the Kessel-Seguin swap needs to be brought up EVERY SINGLE DAY. For eternity.

But unlike other painful trades of the past that continually hurt Leafs Nation's collective psyche (like the Tom Kurvers-pick-that-became-Scott Niedermayer deal that everyone was reminded of as Cody Franson crept up on a Kurvers points streak record), the Seguin trade doesn't hurt. And I'm not just saying that because the Leafs have killed off any feelings I still might have inside of me.