Leafs prospect William Nylander is dominating the AHL despite being young enough to pass for a high school senior.

There are compelling reasons to call him up to the NHL.

• The Leafs are bad and have scored the 6th fewest goals in the league.
• Nylander leads the AHL in scoring with 23 points in 17 games.
• It's his No. 1 goal and he doesn't seem to have trouble with goals.

But calling up Nylander isn't best for the Leafs long-term.

Why?

The Maple Leafs kicked off their rebuild by trading star winger Phil Kessel to the Pittsburgh Penguins for a package of prospects and picks, finally ending the contentious Phil Kessel era in Toronto.

In exchange for Kessel, who goes to Pittsburgh along with Tyler Biggs, Tim Erixon, and a 2016 2nd round pick, the Leafs received Kasperi Kapanen (2014 1st round pick), Scott Harrington (2011 2nd round pick), veteran Nick Spaling, and a 2016 1st round pick and 3rd round pick. The Leafs also agreed to pick up 15% of Kessel's salary, totalling $1.2 million a season.

One of the biggest decisions the Maple Leafs must make this off-season is deciding what to do with Phil Kessel.

Although Kessel is a dynamic offensive player, the Leafs have failed to surround him with talent and the team has wasted Kessel's prime years. There are still good years left for Kessel, but with the Leafs embarking on a full-scale rebuild it's likely those years will go to waste in Toronto. And by the time the Leafs start to rise from the bottom of the league, Kessel will be hitting the decline phase of his career. The wisest decision, therefore, would be to deal him this summer.

But what type of return can the Leafs get for Kessel. Luckily for us, a superstar winger with a massive contract was traded within the past few years and can give us a good idea of what Kessel might fetch in a trade. I'm referring, of course, to Rick Nash.

The Leafs landed the most impactful free agent of the off-season and it isn't even July 1.

On Wednesday, the Leafs signed Mike Babcock to an 8-year, $50 million deal to become the 30th head coach in franchise history.

The Leafs apparently swooped in at the last moment of negotiations and signed Babcock after it looked almost certain as if the Buffalo Sabres would sign the highly sought after coach. There are tears in Buffalo, for sure.

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.