Burke was a dinosaur in the game. What worked 10-20 years ago doesn't work today. When you misevaluate your team to that degree, it's unforgivable. I think the sign of a successful GM is how he manages the assets of the team (Prospects, Draft picks, roster players, etc). Is he making moves that balance the present and the future. Is he going to make a bad trade at the deadline to save his job but damage the future of the organization for personal gain (ala George McPhee in WSH trading away Forsberg for Erat).
I think there are a lot of GMs who set the Leafs back, and Dubas had to clean up their mess and it handcuffed his ability to be as successful as he could be. I think it is extremely difficult to win a cup. There are 31 teams disappointed every year. I think there is a tremendous amount of luck that goes into winning that cannot be accounted for (Team is healthy, hot goaltending, getting the bounces and the calls, other team has injuries, playoff matchup, etc).
People are too results oriented, and not understanding that the difference between winning and losing is razor thin, especially in a league with this much parity. If PIT beats a terrible CHI team, bottom of the league, they would have made the playoffs and knocked out FLA from the WC2 spot. No one would be talking about Bill Zito and Paul Maurice and how they are both geniuses, and what a good signing Bobrovsky was. Nevermind he has been brutal since they signed him, and they couldn't get rid of him for free. He has 10 good games, and everyone forgets.