Ask me about the secret to comedy

Phil Kessel has looked impressive so far, but with the season nearing the quarter mark and the Leafs on pace for their worst point total since the mid-1980s one has to ask - was this the right time for Burke to pull the trigger?

Phil Kessel is undoubtedly an offensive threat with a wrist shot reminiscent of Wendel Clark's. Unlike Wendel, he's also impressed at the other end of the ice, demonstrating his speed with some aggressive and timely back-checking. He's head and shoulders better than any other Leaf forward and it's been a long time since the Leafs had a young talent like this.

That said, I still have a real problem with the timing of the Kessel deal.

This is the type of deal that’s traditionally pulled off by teams with deep farm systems who are close to winning it all.

The Leafs aren’t close to winning most games, never mind competing for the Cup. Their farm team is about as deep as a oil slicked puddle in an empty car park.

The price paid for Kessel was fair but, given the paucity of talent on this club and the complete lack of depth in their system, I'd argue that the Leafs were not in the position to pay that price.

Trading for Kessel when Matt Stajan is your first line centre is the equivalent of a starving homeless guy getting a sub-prime loan and buying a Ferrari.

There are many who claim the Leafs could afford to sacrifice two first round, a second and a third round pick to land Kessel because the team signed NCAA free agents Hanson and Bozak and plucked young goalie Jonas Gustavsson out of the Swedish Elite League.

I totally disagree.

Don’t get me wrong, the NCAA free agents and Gustavsson are great signings, but the Leafs need to do that each and every year for the next two or three seasons, PLUS draft well, just to replenish their prospect pool.

The Leafs have managed to keep their first round pick just three times this decade. Tlusty, Schenn and Kadri are all the Leafs have to show for first rounders since 2000. (Boyes went for Nolan; Cola and Steen for Stempniak; 2003 and '04 dealt for 15 regular and 13 playoff games of Brian Leetch; Rask for Raycroft; the '07 first rounder went for Toskala).

The Leafs won't get another first round pick into their system until 2012.

Given that it usually takes two to three years for a first round pick to make the NHL (never mind make a contribution at the NHL level), once Nazem Kadri makes the jump, it will likely be 2015 by the time the Leafs have their next first round pick in the line-up. Kessel's contract expires in 2014.

For those who argue that players of Kessel's calibre don't hit the open market and teams have to grab them when they do, there's a lot of truth to that; however, every trade deadline produces vets that can push a team over the hump. The Leafs grabbed Leetch, Pittsburgh grabbed Hossa, the Sharks grabbed Campbell, the Stars got Richards, and so on...

Admittedly, most of these players were rentals not multi-year contract holders like Kessel, but the larger point remains: I'd rather build a competitive team first and then look for the much-needed extra part on the trade market. If the Leafs drafted and developed properly, they'd also have a much richer asset base to trade from.

I think the prudent, and most probabalistic path to success in the NHL is to draft and develop well. Get as many kids into the system as possible.

Here’s why:

1. Risk pool – the more prospects the less need for them to all pan out. These are, after all, 18, 19 and 20 year old kids. It’s not an exact science so load up and spread the risk (after Gunnarsson, the Leafs cupboard on D is pretty much empty and that ain’t good).
2. The CBA constrains salaries on players in their first three years, which leads to…
3. Greater cap flexibility as young players outperform their contracts; and
4. Players with less than 3 seasons experience are waiver exempt, creating even more roster flexibility; which means...
5. Teams have the much needed, and rarely found, depth in their system. You develop these kids right and they’ll be able to step right in, play the system and make a meaningful contribution.

In hockey, like comedy, the secret is timing. And I'm not laughing.