08/15/2014 03:12 pm ET Updated Oct 15, 2014

Are the Leafs in a 'Re-Building' Rut?

It is anyone's best guess who Shanahan will hire next week as the new assistant GM to work with Dubas and Nonis. Though the changes do seem exciting - they beg the question 'when will we be a winning organization?' How long will this promised "Culture Change" take?

Chicago went from finishing 13th out of 15 in their conference in the 2005-2006 season to a Stanley Cup in the 2009-2010 season. Most of this is attributed to Rocky Wirtz who took over the team after his father passed in late 2007. Patrick Sharp, the already drafted Jonathan Toews, and the budding Antti Niemi were of course joined by Patrick Kane and the rest is history.

The Kings went from finishing 14th in their conference in the 2006-2009 season to a Stanley Cup in the 2011-2012 season and the 2013-2014 season. The Kings drafted Anze Kopitar, Jonathan Quick and Drew Doughty and made some aggressive moves to bring in Jeff Carter and Mike Richards. The Kings also went through a couple coaches while re-building but finally found leadership success in Darryl Sutter.

Pittsburgh finished dead last in their conference in the 2005-2006 season and won the Stanley Cup in the 2008-2009 season. This was no fluke; the Penguins drafted Fleury, Malkin, Crosby, and Staal between 2002 and 2006. Add in a great move of Ryan Whitney for Chris Kunitz and the veterans like Gonchar, Fedotenko and Letang, (not too mention the ever guiding hand of Lemieux) and the Penguins couldn't lose.

So that's encouraging. History says teams have the ability to turn things around in just a few short years... right? But it seems Toronto and other teams like Atlanta (now Winnipeg) and Columbus and even Florida have been working on their 're-builds' for over a decade now. What gives? Why are we failing?

The Kings, the Blackhawks and the Penguins all focused their re-builds around successful draft picks that they could either build their teams around, or trade for quality players. So lets take a look at the Leafs draft picks from the past couple years. In 2010 we drafted Greg McKegg who has since then played 1 game with the Leafs, 0 points. That same year we drafted Brad Ross who hasn't quite breached the NHL yet. 2010 also saw Sam Carrick drafted who has been successful in sitting mid-pack with the Marlies, and in 2011 we drafted who has done more or less the same. The list of average to mediocre picks goes on. An exception would be defenseman, Morgan Rielly who the Leafs drafted in 2012. Rielly played for the Leafs in the 2013-2014 season and had a very respectable 27-point season.

One notable defenseman draft pick in the past 4 years... that's less encouraging. But as Shanahan stated in his Press Conference on August 14th (Ted Kennedy, Legends Row announcement), "When you talk about making big changes, it's really about doing a whole lot of little things the right way." So let's hope that bringing in Shanahan was the first 'little thing' followed by Dubas, and the much-anticipated second Assistant GM to be named later in August.