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?

The Leafs have signed 2013 third-round draft pick Carter Verhaeghe to a three-year entry-level contract. Verhaeghe will report to the Marlies and join the team for the remainder of the season on an amateur tryout contract.

Verhaeghe improved considerably this past season, exploding for 82 points in 65 games, nearly twice as much as he scored as a 17-year-old. He finished the season ranked 21st in OHL scoring, well behind the 128 points of another Leafs prospect, Connor Brown.

"Trade the pick!? That would require an ability to do more than sit around and pray for the lottery."

A couple of years ago Scott Cullen of TSN wrote a couple great articles breaking down the value of draft picks. It basically broke down how likely a team was to draft a quality player from certain spots in the draft. Amazingly, even if a team owns one of the first three picks there is only a 60 percent chance that player turns out to be at least a top-6 forward or top-4 defenceman. 60 percent! That's crazy.

Here's a graph I made showing how likely a player is to develop into a top-6 forward or top-6 defenceman based on when they are drafted in the first round. After round one the chances are less than 10 percent.

Likelihood of a first round pick becoming at least a top-6 forward or top-4 defenceman.

He also looked at the chances of a player suiting up for at least 100 games in his career. After the first round even that minimal accomplishment is a pretty difficult feat to achieve. In conclusion: drafting is hard!

Likelihood of a draft pick playing at least 100 games in the NHL.

I've used this data to take a look at when it is best for teams to trade up or down in the draft. You can read more at The Good Point.

Last night I went to my first non-NHL game in years. I once saw a Junior-A game as a kid where there was a few fights and as the opposing player was being thrown out the crowd began to chant ‘hey, hey, hey, goodbye’. I was already hooked on hockey by that point, but that certainly made both hockey and fighting infinitely cooler. After that I’ve caught a few random non-NHL games here and there, but I can’t pretend to be an avid follower.

It’s not that I think poorly of any sort of hockey below the NHL, it’s just that I prefer to pay money to see the best players play. But with a top Leafs prospect poised to make a deep run in the OHL playoffs I thought it was time to dust off the ol’ scouting cap and watch the Leafs’ next 100 point scorer cut his teeth (a guy can dream!).

The whole point of this little adventure was to watch Kadri live. This was actually the second time I’ve seen him play, since I was lucky enough to randomly catch his brief one game emergency call-up to the Leafs (February 8th against the Sharks). He held his own during that game, but I wanted to see him play against his peers. I wanted to see him dominate. Yes, that’s how far this season has fallen for me as a Leafs fan. I’ve resorted to travelling across Southern Ontario to watch the future of the Toronto Maple Leafs.