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Did the Maple Leafs Learn Their Lesson?

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The Maple Leafs have apparently decided they are going to do a 'proper rebuild' (whatever that actually means). It won't matter if they don't understand what went wrong.

Bill Streicher-USA TODAY Sports

Around this time seven years ago, the Toronto Maple Leafs fired their General Manager John Ferguson Jr. his poorly constructed team was well adrift of the Eastern Conference playoff race. Cliff Fletcher came in on an interim basis and began to set about trying to move numerous pieces from the roster for future-based returns in order to kick-start a period of rebuilding the team.

Fletcher attempted to move some of the more prominent (and highly paid) players on the roster but has his efforts rebuffed when they exercised their No-Trade or No-Movement Clauses (the infamous "Muskoka Five"). However, he still did manage to shuffle a few pending unrestricted free agents off for draft picks. The moves were pretty standard in today's NHL for a team that has realized they are in a down cycle. Saturday, the Leafs traded a pair of unrestricted free agents, Cody Franson and Mike Santorelli, to the Nashville Predators, for a futures-based return that indicates the official beginning of a period where the Leafs have indicated their intention to rebuild.

Since the corporate message is now one of acceptance that the Leafs are a bad team, the spin has changed from it being all about how awful people our players are to how this time the team is going to be rebuilt right, with patience and drafting and development. After all, we know that devotion to putting a terrible product on the ice and just waiting for the #1 picks to roll in is a panacea that guarantees future success. This is why the Edmonton Oilers and Florida Panthers should be hooking up to contest the Stanley Cup in a few short months although we shouldn't count out those pesky Colorado Avalanche or Columbus Blue Jackets. No, the Maple Leafs are going to "do this rebuild right", a thought so hilariously obtuse and devoid of any actual meaning that people could say the Leafs plan for this rebuild is "purple monkey dishwasher" and it would provide just as much insight into their future plans.

Here's the dirty little secret; in 2008, when the Leafs finally realized the window had closed on the Mats Sundin era, there were specific issues that caused that team to fail. In 2015, now that the Leafs believe that the window has closed on the Phil Kessel era - an era in which no window ever really existed - there are specific issues that have caused this team to fail as well. In fact one of the biggest issues in 2015 is the same thing that plagued the team in 2008. Brendan Shanahan has said many good things about the approach that he wants the Leafs to take and has made hires that appear to speak to that vision but if they don't pay attention to what went wrong with that first rebuild and avoid the same mistakes down the road then this rebuild is dead before it even begins.

Let's go back to 2008 once more and try and identify the problems that the Leafs had that led to Ferguson being fired. Goaltending was obviously the team's Achilles heel. Andrew Raycroft, Vesa Toskala and a raft of other "pray for something amazing" candidates were handed the crease in the hope that one of them would take up the mantle from Felix Potvin, Curtis Joseph and Ed Belfour. Goaltending was a major stumbling block after the 2005 lockout and it cost the Leafs dearly both in missed opportunities to make the playoffs and in the future assets that were expended in trying to fill the post-Belfour void.

Future assets were another problem. Prior to the lockout, the Leafs operated in a different landscape, where draft picks didn't hold value to the same degree they had before. They were a team that was trying to win and could paper over the cracks with veteran free agents so draft picks were a currency that could be used to pursue those tantalizing missing pieces. The Leafs had the misfortune of shipping out several picks during a high water mark for new talent entering the league (the Leafs got very little out of either the 2003 or 2004 draft), and simply didn't have much in the way of prospects that could be counted on for immediate relief. Ironically the 2006 and 2007 drafts would prove to be a high water mark with the former scout Ferguson at the helm with his new Head of Amateur Scouting, Dave Morrison. These drafts produced several players that would become established players on the Maple Leafs.

But the problem that was at the root of the decision to rebuild was that the salary cap had changed the ways in which a team could plan to get better and the Maple Leafs had not adapted well to the new salary cap world. The Leafs roster was quite old relative to the rest of the league and relied on a large number of veteran players on expensive free agent contracts that were near impossible to move thanks to the advent of NTC and NMCs. These were a major constraint on a GM's ability to improve his team. The fingers were pointed at the people with the biggest contracts (Bryan McCabe, Pavel Kubina, Tomas Kaberle, Jason Blake) as the root causes of the Leafs cap problems. However, the Leafs had paid market value for players that had a history of proving themselves to be worth it, only they didn't account for the inevitable decline as players aged. In this case, there are definite parallels between the Leafs and the present-day New Jersey Devils.

So what about now? Seven years later, operating under the salary cap has become much more sophisticated. The understanding of the value of drafting and development is paramount and teams are significantly less likely to part with major draft picks or prospects unless absolutely necessary. In addition, the advent of work done in statistical analysis gives front offices that choose to use them powerful weapons to identify gaps in conventional thinking and squeeze advantages out of the marketplace.

This time around, goaltending isn't nearly the problem. The Leafs goaltending carousel, both past, present and future is well-covered ground. But had the Ferguson Leafs had Jonathan Bernier and James Reimer as their goaltending tandem, those Leaf teams would have made the playoffs. The Leafs receive value for the money they currently pay for their goaltending.

Future assets still remain something of a problem. If you're familiar with my opinions on Dave Morrison - I think after Randy Carlyle and Dave Nonis he's the man most responsible for the current plight of the Maple Leafs - then you know that his drafting record since 2007 is astoundingly poor. Luke Schenn, Nazem Kadri, Morgan Rielly. That's the sum total of Leaf-drafted players developed into NHLers since that 2007 class. And it's not like they happened to trade away a whole bunch of guys that then blossomed into pros; that list consists of 2008 pick Jimmy Hayes. Four pros in seven years. That's atrocious, even when you discount for the draft picks traded in that span. (Picks that it should be pointed out were turned into Mikhail Grabovski, Schenn, Phil Kessel, Peter Holland, Bernier, among others).

The addition of Mark Hunter should aid with the drafting performance but there's so much inherent uncertainty that it's hard to know whether you've improved your draft and development process adequately until it actually begins to bear fruit.

To find the real reason the Leafs find themselves facing the verge of another need to rebuild is simple; they didn't learn any lessons about managing their salary cap.

Even though we spent four years prior to this one hearing the excuse that the Maple Leafs were one of the youngest teams in the league (the most "technically correct" statement ever), the Leafs didn't prioritize development. They hired a coach that doesn't play young players and jerked around so many young players and potential future pros that it actively undermined some of the work that the scouting department did that might have produced some cheap, effective, home-grown players.

Instead, the Leafs cap is saddled with numerous bad contracts for players that have declined from what they once were (Joffrey Lupul, possibly Dion Phaneuf), are coming to an age where they will begin to decline shortly and are not likely to continue to hold value (Leo Komarov, Tyler Bozak), and massive contracts for mediocre, replaceable players which have rendered them virtually immovable (David Clarkson, Stephane Robidas). This list could be even worse as the Leafs attempted to sign Dave Bolland to a massive contract extension this past summer and prior to that attempted to trade for and then extend a washed-up and about-to-retire Miikkaa Kiprusoff before pursuing Martin Brodeur! Or that they botched their compliance buyouts so egregiously that instead of moving Komisarek to the Marlies and buying out John-Michael Liles which would have cleared both contracts in one year, they used their final compliance buyout on Komisarek, let JML get buried, then traded him for Tim Gleason who turned out to be worthy of a regular buyout. The net result is that Tim Gleason will now count against the Leafs cap for four years.

The thing that is the most frustrating about the Leafs cap situation is twofold. First, it was entirely preventable. The Leafs have made so many frustratingly bad decisions in the last three years that it speaks to a complete inability to understand the necessities of the salary cap. "It's just an overpayment of a million" here or "it's only half a million of retained salary" there adds up to a lot of salary cap space wasted especially when you finish 22nd in the league and somehow pay a bonus overage on a team whose coach doesn't play rookies. Or how you keep playing contract games with a defenceman who is slowly developing into a useful top four defender only to have no cap space available to be able to offer him market value and you have to trade him before he becomes a UFA. Or how you make a prudent decision to let a one-time 30 goal scorer go because his production has tailed off and his new team signed him to a very rich contract. Except only this is one year after you were the team offering the rich contract while including the caveats that "he wasn't brought in to score goals" and that "I'm not worried about Years 6 or 7 of this deal". Which is a good thing to say when it's possible that he gets bought out after Year 2.

But the second thing is that this was predictable. In fact, we predicted it. Multiple members of this site and other voices in the media pointed out repeatedly that the Leafs cap situation was a ticking time bomb. Now it's gone off and the Leafs are left in the same position they were seven years ago; pressed to the salary cap with no shortage of old, mediocre, declining, expensive contracts, and some real headaches on how to fit the important pieces that might survive a rebuild into the cap going forward. The only real difference between this team now and this team seven years ago is that this time around our best player is turning 28 years old, not 38.

Dave Nonis ruined this team's chance at contending in such an astonishing fashion and with virtually no consequences from a media that was effectively bought and paid for. They've resorted to frequent and increasingly tone-deaf and logically inconsistent attempts to explain the fact that this team had been set up to potentially progress and that Nonis cut its legs out from under it. Dave Nonis remains employed and is now trumpeted as a veteran voice to help the new faces in the front office, indicating that useless leadership has migrated into the gondola of the ACC as well.

I respect Brendan Shanahan's work in the Department of Player Safety and want to believe that he is suited to be the person to steer through the wreckage. But I also remember that he's the one who put Dave Poulin and Claude Loiselle on the market where they were immediately snapped up by any number of hockey teams. I mean, I assume that they did because Darren Dreger said they would be hired quickly. And while he brought a number of new voices from a number of different viewpoints to help set the team's new path, he's also the guy who extended Randy Carlyle.

But the lesson as to what went wrong with the Leafs, and really what continues to go wrong with the Oilers to a certain extent, has been staring anyone willing to look in the face for near a decade. This is the third management group to take a crack at building the Leafs into a consistent winner since Ken Dryden and the late Pat Quinn showed up over 15 years ago and turned the Leafs around. The problems remain the same, and no amount of compete or leadership can make up for a bad front office.