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 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.

"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.

From the press box to the top defensive pairing, Cody Franson has come a long way in his four seasons as a Maple Leaf. Now in the final year of his contract the Leafs have to decide whether he's a key piece for their future or whether he's expendable.

For a while it looked like Franson was merely a bottom-pairing defenceman with a good shot capable of racking up points on the power play. Now Franson has become the Leafs best possession defenceman while playing alongside Dion Phaneuf on the top pair. When Franson takes the ice the Leafs gain a shot advantage they haven't enjoyed in years; the team controls 50.1% of all shot attempts with Franson, and fall back to their customary shelled selves when he takes a breather.

Once again it looks like the Vancouver Canucks' trash is the Toronto Maple Leafs' treasure. Last year the Leafs snagged Mason Raymond on a bargain deal and this year Dave Nonis went to his old team to pluck the freshly bought-out David Booth on a one-year deal worth $1.1 million.

Raymond was highly motivated in his stint in Toronto after being tossed aside by the Canucks, producing 45 points for a measly $1 million. Raymond's 19 goals as a Leaf was his best output since scoring 25 in 2009-10. The hope with Booth is that he can reclaim some of the form that saw him net 31 goals with the Panthers way back in 2008-09.

The Leafs finished last season ninth in team save percentage, meaning after years of wandering in the wilderness they have finally solved their goaltending problem. But nothing is simple in Toronto and even the team's biggest strength comes with plenty of tough questions.

The Maple Leafs problem isn't scoring goals, it's keeping them out. But after being a top-10 team in goals scored from 2011-2013, the Leafs were middle of the pack last season suggesting defence isn't the only area in need of an upgrade.

The Leafs rely heavily on Phil Kessel and James van Riemsdyk and many nights live and die with their power play because apart from those two first liners they have trouble generating chances at even strength. A total revamp of the defence is the first priority this off-season but so too is creating a more balanced attack up front. Thankfully, the forwards need more of a tweak than a gut job.

Dave Bolland wants to be a Leaf for life, and a fellow Mimico boy might help make it happen.

“I’d like to get him signed,” Brendan Shanahan told the Toronto Sun a few weeks ago. “He’s the type of player I like, the type of player we need."

There's a lot to like about Bolland. He comes with a winning pedigree, grit, leadership, and the type of blue collar work ethic that plays well with the Toronto crowd. He's the type of player that does the little things that help a team win. But that doesn't mean the Leafs should break the bank to keep him.

According to Steve Simmons, the Leafs don't want to pay Bolland any more than the $4.2 million a season they are paying Tyler Bozak. That means there's a disconnect between the two camps, because Darren Dreger reported at the end of February that Bolland could be looking for as much as $5 million a year, and maybe more.

With close to $49 million already committed to only 12 players next season, giving Bolland anything more than $4 million a year means the Leafs view him as a core piece, rather than a complementary one, like he was in Chicago.

That would be a major mistake.

Winners of 15 of their past 22, the Leafs will have to continue their surge without the efforts of No. 1 goalie Jonathan Bernier, who left Thursday's game against the LA Kings with a lower-body injury.

Although the injury is not considered serious, Bernier did not practice with the team ahead of Sunday's matchup against the Capitals. The Leafs also recalled Drew MacIntyre from the Marlies to serve as James Reimer's backup.

At this point there is no timeline for how long Bernier will be out, and the task of guiding the Leafs down the stretch and into the playoffs could conceivably fall upon Reimer, the man who Bernier has soundly beat out for the No. 1 job this season.

But should Leafs fans worry? Is the drop off between Bernier and Reimer as steep as the numbers so far this season suggest?

Very rarely does a sixth-round pick turn himself into a legitimate prospect. But as Leafs prospect Connor Brown continues his assault on the OHL, more and more fans and scouts are beginning to wonder whether Brown's scoring prowess will one day translate to the NHL.

Brown is leading the OHL in scoring with 31 goals and 92 points through 45 games and is on pace for nearly 140 points. No OHL player has surpassed 130 points in a season since Patrick Kane scored 145 in 2006-07.

On the one-year anniversary of his hiring as Toronto Maple Leafs general manager, Dave Nonis is witnessing his team implode. Toronto has only two regulation wins in their last 23 games and only four in the 30 games since a 10-4 October.

After making the playoffs last season the Leafs have taken a gigantic step backwards in 2013-14, although they are miraculously still in a playoff spot thanks to a terrible Eastern Conference.

Now seems like a good time to evaluate Nonis' first year on the job.

On the day of the Winter Classic the Leafs made a trade, consummating the oft-talked about John-Michael Liles for Tim Gleason swap with the Carolina Hurricanes.

The deal is a lateral move, both teams dealing overpriced defenders with two additional years on their contracts, but one in which the two players might provide better results with a change of scenery.

The Winter Classic is really, really cool and breathtakingly beautiful. It also really sucks.

Don't get me wrong, walking into the Big House and looking around at the enormous crowd as the snow fell and the teams took to the ice is a moment I'll never forget and it was every bit as magical as you expect. Magic doesn't keep you warm, however, and about five minutes into the game you start to question your own intelligence.

Dion Phaneuf is on the verge of signing a seven-year extension with the Leafs, valued at $7 million per year. The cap hit comes with major sticker shock, but it's a deal the Leafs needed to make.

The tide might be turning against Randy Carlyle.

After a quick start to the season has been erased by an awful November and the first few weeks of Deathcember, the shine on Carlyle, the coach responsible for ending Toronto's near decade-long playoff drought, is starting to fade. Last year many of his moves were roundly criticised by the blogosphere and some of the saner elements of the mainstream media (shout out to James Mirtle!), but the Leafs were winning, so for the broader portion of newspaper writers and television analysts Carlyle could do no wrong.

The same reverence for Carlyle no longer exists. Many of his puzzling moves are being questioned by pundits who might have looked the other way last year. Winning cleans up a lot of mistakes, even those made by coaches.

With the Leafs in the midst of a tailspin, the vultures are looking for easy scapegoats, and as always, some in the mainstream media are pointing fingers at the wrong guys.

Simmons "Kadri has basically gone from an 80 point guy to a 50 point guy" Still better than Bozak and not on the top PP or on the top line
— Hope_Smoke (@Hope_Smoke) December 3, 2013

It is a dark time for the Maple Leafs. Although the playoffs drought has been destroyed, the opposition has driven the Toronto forces from their lofty Eastern Conference perch and hammered them across the conference. Evading the dreaded regression monster, a group of heroes led by James Reimer and Jonathan Bernier have established hope on the ice. The evil lord Carlyle, obsessed with allowing the most shots ever, has dispatched thousands of forwards onto the far reaches of the bench to allow more ice time for Tyler Bozak....

After one game of Jay McClement as the team's best natural centre, the Leafs addressed their desperate need down the middle by making a deal with the Anaheim Ducks.

The Leafs acquired Peter Holland and Brad Staubitz from the Ducks on Saturday, shipping out Jesse Blacker, a conditional third-round pick (that could become a second-round pick if he plays 25 games), and a seventh-round pick (which was originally Anaheim's).

The primary parts of the deal, Holland and Blacker, were both blocked in their respective organizations, with Anaheim deep at centre and Toronto deep on the blueline. Blacker had fallen so far on the depth chart in Toronto that he has been a healthy scratch for much of the year with the Marlies.

Dave Nonis did well to deal from a position of strength to get a quality NHL-ready prospect when the Leafs were in such dire need for help.