Maybe I’m overly cynical. Maybe the Dryden / Quinn / Ferguson years so soured me that I lost all hope – that I cannot even begin to believe that a Leafs team could really contend for the cup. Maybe I’ve lost all perspective. Maybe my claims to big picture thinking are really just rationalizing disguises for a deep-seeded pessimism about Toronto hockey that is a completely emotional. Maybe I hate Burke’s arrogance so much that I can’t see the good he’s doing.

Sometimes I really wonder: Even non-Leafs-fans are telling me the Leafs are going in the right direction. Am I crazy? Is my suspicion that this team is a long way off from contention totally unfounded?

It is appearing more and more like that every day. Leafs fans obviously buy in. But certain ever-skeptical members of the media are now buying in. And friends and coworkers who dislike or even hate the Leafs are buying in. So why am I not? Is it blatant irrational cynicism?

The thing is, I don’t want the Leafs to just contend. The Leafs have contended, off and on, for nearly fifty years. There have been some really low points, like our recent past and the early ’80s, but on the whole, the Leafs have almost always contended. They have been a playoff team far more often than not. They have regularly had decent (though rarely ever great) players. They have put up impressive regular seasons. They went through a stretch where they went to four conference finals in 10 seasons, certainly better than average.

But that’s it. They won no cups, as we all know. They have been to five conference finals since ’66-’67, but not a single final. In the last three conference finals, they got their asses handed to them (especially in the last one). And this is what I want to avoid.

We can look back at the ’92-’94 teams with nostalgia because they were pretty competitive. But the excuses we make as to why they didn’t make the finals are just excuses. It didn’t just revolve around one play. The other teams were better.

We can’t really look back at the ’99 and ’02 teams with such nostalgia. They went on fairly unexpected runs both times and got humiliated. (Like I said, especially in ’02, when they scored something like 6 goals in 6 games in the Conference Final.)

Those sniffs at contention were just that, sniffs. And they were accomplished through a really silly process where every year Dryden, Quinn or Ferguson evaluated the Leafs, decided they were 1-5 players short of a cup contender, and traded the future away for such (inevitably ancient and / or injury-prone) players. The result? Two conference finals appearances…but in reality they were mostly because of Cujo. (Back in the day, for those of you who don’t remember, the Leafs seemed to get out-shot every night, but they somehow won all the time.)

Between and 1993 and 2008 (15 years), when the Leafs drafted Schenn fifth overall, the Leafs had one – that’s right, I said one – top 10 draft pick: and they used it to draft Antropov. They drafted a number of okay players later in the first round, and lots of other not so okay players, and traded most of them away.

That’s why such a strategy doesn’t work. That’s why such a strategy eventually ends in a huge playoff drought. Therein lies the renewal. It would have come much sooner only they traded for Mats. By trading for Mats they extended the length of the franchise’s run of competitiveness for the length of his career, or thereabouts. When he ceased to be a factor, so did the team.

Why? Because the Leafs were never bad enough to acquire anyone to replace him.

Then, they had their chance. But a certain someone traded it away…twice. I know we’ve gone over and over that deal, but it is important to do it again in order to explain why I think this “rebuild” isn’t going anywhere. The Leafs lack a star. Kessel is not a anything more than a top 3 forward in the league and he’s not even that some nights. The only way the Leafs can currently acquire a star is through a trade or free agency as they do not have the picks – provided of course they don’t luck into somehow drafting the best players in the draft this summer with their 24th and 29th picks. Free agency means overpaying and probably signing the guy to a longer contract than is reasonable. Trading means giving up much of the substantial supporting cast Fletcher / Burke built up. Either way is not as good as getting it through the draft, like Edmonton.

That’s why I’m cynical. It’s not that I want the Leafs to be perfect before they contend. It’s that I want them to do more than contend. It’s that I want them to win a cup or more, and challenge for the cup every year, like Detroit has for so many years. And the only way anyone knows of doing that is by following the course Edmonton is currently taking. It may not work (if often doesn’t), but it has a far better chance of working than whatever it is the Leafs are doing right now.

Think about it this way: how many NHL teams have won the cup without tanking beforehand, or without somehow trading for the picks of a team that sucks donkey balls?