An anonymous comment over at my blog Bitter Leaf Fan raised the question of how exactly the Leafs arrived in their current mess.

There’s not a single cause or easy explantion.

This franchise has gone through three, maybe even four, different phases since 2000, however; with the exception of one small window, all of these phases have focused on the short-term, sacrificing picks and prospects for a supposed fix.

After the jump, a look at the Leafs' propensity to deal away the future and the pile of pocket lint, loose change and used gum wrappers they got in return.


The Pat Quinn teams of the early 2000s were powerful clubs. Each made the playoffs and several flirted with 100 point seasons. They combined a nice mix of talent and flair (Sundin, Mogilny) with grit (Roberts, Tucker) and solid goaltending (Cujo, Belfour).

These teams were often legitimate threats to go deep in the post season and on more than one occasion it was widely thought they could challenge for a cup. As a result, these teams made a number of trades where the future was sacrificed for the present. There was a small window of success and the Leafs went for it, selling off the future in the hopes of a big pay-day.

In 2003, the Leafs trade Brad Boyes (2000 1st round pick), Alyn McCauley and a 1st round pick for Owen Nolan

In 2004, the Leafs trade two prospects, a 1st and 2nd round pick for Brian Leetch.

In addition to dealing away those three first round picks, the Leafs also had some bad luck when their 1999 first round selection (and WJC 1st team all-star) Luca Cereda had to hang up his skates due to health complications with his heart.

From 1999 to 2004, the Leafs emerged with just two first round draft picks: Carlo Colaiacovo and Alexander Steen. Both would later be traded to St. Louis for Lee Stempniak.

The Missing Years

John Ferguson Junior’s tenure was like a ship lost at sea…or maybe it was a ship that kept running into ice bergs…or a lost ship, on fire, that kept hitting ice bergs. Choose your own nautical disaster metaphor and, in keeping with JFJ’s reign of error, the more apocalyptic and dire your selection the more accurate it will be.

Ferguson was GM from the 2004 to 2007 drafts.

Out of those five drafts, he managed to hold on to his first round pick in just once – giving the franchise Jiri Tlusty and a whole lotta NSFW jokes.

Unable to shake-off the "win now!" edict from the MLSE board, in just two years Ferguson sacrificed two first, a second and a fourth round pick in an effort to shore-up the team’s goaltending. Some four years later, goaltending remains a position of weakness that hasn’t been adequately addressed.

JFJ's draft day magic:

  • The 2005 first round pick (Tukka Rask) dealt for Andrew Raycroft.
  • The 2006 first round pick was Jiri Tlusty.
  • The 2007 first round and second round picks (along with a 2009 4th) to San Jose for Vesa Toskala.
  • The 2008 second round pick to Phoenix for Yannic Perreault.

Draft Schmaft Redux?

In 2008, Cliff Fletcher was brought in to try to move out the NTCs/NMCs on the club and start the, ahem, rebuilding process.

Given the need to get more talent into the system, he made some, shall we say, curious moves:

In fairness to Fletcher, he also acquired a small parcel of picks:

An Eye for Talent? Um. Not really...

If you’re going to trade away picks and prospects, the returning players better pan out.

Clearly that has not been the case for the Leafs.

By my math, the Leafs traded five first round and three second round picks for the following return:

  • 69 games from Owen Nolan.
  • 28 games of Brian Leetch.
  • 91 games (and 268 goals against) of Andrew Raycroft (plus a multi-year buyout)
  • 17 games of Yanic Perreault
  • 127 games (and counting) from Vesa Toskala/

Stop and marvel at that return.

Five first and three third round picks for 332 games played (plus Toskala's starts until the end of the season).

I'll spare the Leaf defenders from doing the math - Brad Boyes, one of the former first rounders traded away, has played 347 NHL games, 15 more than this motley collection managed for the Leafs.

What's worse is that every single one of these players left the Leafs without a single asset coming back in return.

I'll wait while you drink it all in.

I don’t know about you, but I don't think there’s an adjective that can adequately summarize this. One could argue that only Bernie Madoff has done a worse job of asset management - and even that might be a stretch.

Making Mistakes Beyond the Draft

Even more painfully, that poor return only reflects the draft side of the equation.

The Leafs have not excelled in the free agency department (Blake, Finger), have made poor decisions in awarding NMCs and NTCs, and have made a series of poor decisions on talent retention – signing McCabe, Tucker and others to long-term deals rather than trading them at peak value. But I’ll save that rant/analysis for another day…

For now, in a nutshell, this is a good first step toward building a franchise that’s on target for a 50 point season and has limited options at hand.