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?

Morgan Rielly is making life very difficult for Dave Nonis and the Toronto Maple Leafs.

The 19-year-old defenceman made the Leafs out of training camp and has looked good so far with the big club. Rielly has four games remaining before the Leafs must decide whether or not to keep the talented blueliner or send him back to Moose Jaw to play in the WHL. Once Rielly plays his 10th game as a Maple Leaf the first year of his entry-level contract will kick in and he's here for good.

It's a very complex decision and not one management will take lightly. There are pros and cons to keeping Rielly and Nonis has a lot to weigh before making the decision.

To help him out I've summarized the debate in a segment called "Point/Counterpoint".

Training camps are open and that means hockey is back. Huzzah, we are safe to watch Sportscentre highlights again!

It also means there is plenty to write about, unless you're super lazy, in which case you can dust off your notebook and pick from one of the tried and true cliché storylines that comes up every training camp. Just add in different names from this year's roster like a Mad Libs story and you're set.

Stick tap to this Bill Simmons article for the inspiration.

Four years ago the Leafs rushed an 18-year-old Luke Schenn to the NHL, and it looks like the team is prepared to do the same with Morgan Rielly.

“I’m gonna pick the best players,” Randy Carlyle told the Toronto Star. “If (Rielly) is among the best, I’ll have no qualms picking him because he’s 18.”

Management has echoed the coach's philosophy.

“If Morgan Rielly can help our team win, I really don’t care that he’s only 18,” Dave Nonis told the National Post. "If he’s ready, he’ll stick around."

The hope would be that Rielly could help upgrade the Leafs' blueline, one which has been near the bottom of the league for years. He is a slick-skating, puck-moving defenceman that could potentially step in and provide a reasonable facsimile of Jake Gardiner, who is currently out with a concussion.

The Leafs can give Rielly a five-game try-out (a sixth game automatically burns a year on his contract), but allowing him to make the Leafs this season, regardless of how NHL-ready he may appear, would be a monumental failure.

Four years ago today Brian Burke took over the Toronto Maple Leafs. His reign has coincided with one of the worst four-year stretches in team history.

On average, GMs last between five and six years with one team. If the Leafs once again fail to make the playoffs in Burke's fifth season as GM, ownership will have to seriously consider changing leadership.

After next season, Leafs ownership has two options: 1) fire Burke immediately, or 2) commit to Burke long-term. Giving Burke any more than one year to guide the Leafs, but less than a long-term mandate, will be catastrophic.