The difference between the two organizations over the past 6-7 years: Brian Burke, and climate.
All teams fall under the same mandate - continue to improve your organization by acquiring assets of greater value. They can do this via draft, trades and signings. All routes need to be pursued to continue to improve over the long haul. The current Leafs' roster has been built by drafting guys like Kadri and Rielly, trading for guys like JVR, Lupul, Gardiner, Kessel, Phaneuf, Franson, Bernier and Bolland, and signing guys like Clarkson and Ranger. Not always going to hit a home run with every acquisition, but that doesn't mean any one means is more important than the other.
When a team is absolutely terrible, they typically draft high and look to obtain their next franchise player(s). These are no brainer picks, and if you're really bad and you get lucky at the same time, you end up with a Crosby or Ovechkin. These types of players don't come around every draft year. Sometimes draft years are weak, and poor performance from the year before doesn't guarantee anything great at the draft table. It's not a perfect science. Just ask Cliff "Draft Schmaft" Fletcher.
The Oilers are a pretty bad team to compare anyone to - the market is very different. I think its much tougher for their management to attract and retain players than most (if not all) teams in the league - just comes with the territory of being situated in a city like Edmonton. They're kind of like the Blue Jays of hockey. Most players, if they had the choice, would likely want to play elsewhere. So, they are forced to try and build more through draft picks than most other teams, hope they can make good trades and pray that they can attract good free agents.
The Leafs' rebuild has been somewhat unorthodox - kudos to Brian Burke for swinging some pretty great deals to get the Leafs back to respectability. Typically, trades are not easy to construe and hard to get to a point where both teams feel like they're improving their club, which is obviously essential for the trade to happen. Burke was able to achieve this with the deals for Lupul/Gardiner, Franson, Phaneuf and JVR. Pretty amazing, IMO. The Kessel deal was unique, and at the time it was made, it was the acquisition of a young kid with superstar potential who already proved himself at the NHL level, for a potentially high draft pick that came with more risk. Bird in hand, as they say. Signings are always tough, as you're typically overpaying guys for their past performance. Aside from Clarke MacArthur, this has not been an area where the Leafs have succeeded since BB took over, but I give them a pass, as it is the riskiest of the three routes.
The Oilers, on the other hand, have drafted good players (and its not that tough when you pick 1st overall who to chose), but haven't done much else to build the rest of their roster. Very different approach than Toronto, but likely not by choice, more so by circumstance.
I'm very interested now to see if Burke can work similar magic in a tough market like Calgary.
GLG