Toronto Maple Leafs: Past Mistakes Explain Why They're So Screwed Now

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Toronto Maple Leafs: Past Mistakes Explain Why They're So Screwed Now
Rich Lam/Getty Images

Leafs Nation is growing weary of the Maple Leafs' constant struggles over the past six (or 44) years.

But just how drastically different should things have turned out?

Hindsight is 20-20. Looking at recent decisions does not suggest that Leafs' management should have been perfect and built the best dynasty in sports history, but rather only a few key issues have killed the Leafs and their future.

The biggest problem, by far, has been the trade culture of the Leafs in the last few years. When the Leafs thought they were semi-contenders, like in the early-to-mid 2000s, they traded away first round picks three times (2003, 2004, 2007) and second rounders five times.

They never acquired a single first round pick, except when flipping first round positions.

When it came to trade deadline day and entry draft day, if the Leafs thought they had a even the smallest chance to make the playoffs, they dumped off high draft picks for aging veterans with little left in the tank.

However, when the Leafs have been in the position of power and had the aging veterans that other teams coveted, they've refused to make the moves for picks and prospects.

Since 2003, the following players have walked away as unrestricted free agents (or retired) after not being dealt: Mats Sundin, Joe Nieuwendyk, Gary Roberts, Robert Reichel, Alex Mogilny, Mikael Renberg, Ron Francis, Ed Belfour, Brian Leetch, Eric Lindros, Jeff O'Neill, Kyle Wellwood, Jason Allison and Curtis Joseph.

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A large part of that list are current or future Hall-of-Famers and their departures left the Leafs with severely depleted assets in terms of prospects; the same thing is sure to happen with Tomas Kaberle at the end of this season.

Next, consider a few of the trades the Leafs have made, including last season's Vezina finalist Tuukka Rask to Boston for Andrew Raycroft, two first round picks and a second rounder to Boston for Phil Kessel, Adam Mair and a second rounder (Mike Cammalleri) to Los Angeles for Aki Berg and Brad Boyes, Alyn McCauley and a first round pick to San Jose for Owen Nolan.

Add to that a bevy of ridiculous signings attempting to make up for the lack of talent and lost opportunities, such as Darcy Tucker's $12 million over four years, Jeff Finger's $14 million over four, Mike Komisarek's $22.5 million over five, Pavel Kubina's $20 million over four, and Jason Blake's $20 million over five years and you start to wonder if the Leafs pick their GMs out of insane asylums.

And I didn't even mention the recent Beauchemin, Orr, Armstrong, or Lebda debacles.

The entry draft history is also pretty ugly. Starting with the great draft of 2003, in which the Leafs best pick was John Mitchell, they've managed to draft seven players who have become NHL regulars, only four of whom are still with the Leafs. Tuukka Rask, Nikolai Kulemin, Anton Stralman and Luke Schenn are steady players (in terms of playing virtually every game, not their actual play).

Jeff Vinnick/Getty Images
Richards & Perry 2005 WJHC Gold

Nazem Kadri is well on his way, but John Mitchell and Viktor Stalberg are borderline NHLers at best.

Now, here's where it gets a little more complicated: When the Leafs traded away three first rounders in the middle of the decade, they received Owen Nolan's 50 points in 79 games before leaving, 15 points in 15 games from Brian Leetch and 62 wins with 74 losses, a 3.08 GAA and .894 save percentage from Vesa Toskala.

If the Leafs hadn't made these trades, the 2003 first rounder could have been Ryan Kesler, Mike Richards, Corey Perry, Loui Eriksson, Patrice Bergeron, or Shea Weber. The 2004 pick could have been Mike Green, David Krejci, Wojtek Wolski, Alex Goligoski or Brandon Dubinsky. Finally, the 2007 pick could have been Kevin Shattenkirk, Max Pacioretty, David Perron, PK Subban, TJ Galiardi, Wayne Simmonds or Jamie Benn.

I think it's safe to say the Leafs completely wasted all three first rounders.

Even with the first round picks the Leafs kept, they've struggled badly. In 1999, they picked Luca Cereda two spots before a fellow named Martin Havlat went to Ottawa. In 2002, they went with Alex Steen, who hasn't been bad but doesn't have Stanley Cup wins like Cam Ward or Duncan Keith, who were picked soon thereafter.

In 2006, they picked Jiri Tlusty. Do you remember him? They could have chosen Chris Stewart, Claude Giroux, Semyon Varlamov, Patrick Berglund, Steve Mason or Milan Lucic!

Chris Trotman/Getty Images

Even their later round picks have been brutal.

When the 2004 first rounder was traded for Brian Leetch, John Ferguson Jr. packaged it with the Leafs second rounder in 2005. That pick could have been Paul Stastny, Guillame Latendresse, Kris Letang, Ondrej Pavelec or Jonathan Quick. Also in 2005, the Leafs picked Phil Oreskovic in the third round, shortly before Keith Yandle.

In 2004, they picked Justin Pogge—the eventual reason for dumping off Rask— just ahead of Johan Franzen. In 1999, they were one spot off Henrik Zetterberg in the seventh round, and in 2000, just missed Henrik Lundqvist at pick 205.

It's too early to tell for the 2008, 2009 and 2010 drafts, but Tyler Myers went seven spots after Luke Schenn and Jordan Eberle was ten picks after Myers. In 2009, Kadri went ahead of Magnus Paajarvi, and a dozen or so current World Junior stars.

Then in 2010, the Leafs missed out on Tyler Seguin on order to have Phil Kessel. And who knows, without Kessel it might have even been Taylor Hall, who is only one goal behind Phil and has twice as many since the end of October.

If the Leafs aren't an argument against any GM ever trading away a first round pick, I don't know who is.

So, if the Leafs hadn't traded away a pile of draft picks, had traded Mats Sundin at the 2008 draft (to Vancouver for Kesler and a first round pick) and had drafted a bit better, not by any means perfect, but picked quality first rounders and hit one late round gem in the decade, they could be looking at a line-up something like this:

Dave Sandford/Getty Images
If only they'd switched teams...

F1: Henrik Zetterberg, Mike Richards, Mike Cammalleri

F2: Chris Stewart, Paul Stastny, Martin Havlat

F3: Milan Lucic, Ryan Kesler, Jeff Skinner

F4: Wayne Simmonds, Nikolai Kulemin, Clarke MacArthur

D1: Duncan Keith, Mike Green

D2: Luke Schenn, Tyler Myers

D3: Tomas Kaberle, Kevin Shattenkirk

G: Cam Ward, Tuukka Rask

Obviously, with the salary cap, this roster isn't feasible to keep. But if the Leafs had gathered these assets throughout the decade, you can be sure the team would be a contender for years to come.

I guess it just goes to show how bad Leafs' management has been over the past ten years.

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