Phil Kessel Trade: Who won?

Many people - media, fans, Hockey execs - always seem to debate on who 'won' this or that trade. Judging these things can be difficult and it usually falls to history to answer the question. People can debate player stats and the meaning each player had to their team etc. But how do you judge a player-for-picks deal?

Read on for my perspective.

The basis for my opinion lies in the following statement: You cannot ever properly compare a player-for-pick trade. The only thing you can do is answer the question: Did the player we get live up to the expectation? More on that later.

First, the value of draft picks are fluid in so many ways. Take for example the Leafs picks they traded - 2010 1st and second and a 2011 1st.

1) The intrinsic value of these picks on the day Burke traded them will be different tomorrow, a week from now, a month from now and during the drafts in which they are used. Today, the deal made sense, 6 months from now, who knows? That is all part of managing your risk/reward aspect of making a trade.

2) The depth of the draft. Many have speculated that the 2010 draft will have 3 sure fire players at the top and then 7 legitimate elite prospects to round out the top 10. After that, there is a wide variety of depth that is difficult to evaluate. This was one of the factors in Burke's decision. The thing is, could several players come into their own this season, thereby increasing their value with the scouts? Yes, that's possible, but it is also possible that some players will see their stock drop as the season progresses. Let's not even try to speculate how the 2011 draft will go, considering those players are either 16 or turning 16 this year.

3) What is also very fluid is where these picks will be taken. If the Leafs take a step back this year and have a bad season(for various reasons) and this turns out to be a lottery pick, then that obviously increases the value of the picks. On the other hand, if the Leafs make it into the playoffs, the highest their pick can be is 14th - outside of that important top 10 mark. Not only do the players in the draft have an affect on who is ranked, the play of the Leafs also heavily factors in to the draft order. Also, this trade can directly affect how the draft ranking is determined depending on the level of contribution of Kessel.

4) Who's to say that even if the Leafs had kept their picks that they would have picked the same as the Bruins? The Bruins are a team at a different stage of development to the Leafs and have different organizational needs. Although it is an opinion, I believe the Leafs are at least 2 and probably closer to 3 years behind the curve of competitiveness that the Bruins are currently at. To make things more complicated, what happens if the Bruins trade these draft picks for other players/prospects/picks... the water becomes more muddied.

So, All that and we still haven't drafted any players.

Now you draft your players and we have to consider the following:

Organizational depth: how good are the players on my team by position? If you have a strong team already, how much time will they spend in your development system? How will that affect their development? If they were in another team's system would they get a chance sooner? How would they develop differently in another team's system?

When you look at these questions, you can't begin to assign a value. These are the intangibles that can't be quantified in any meaningful way. And what about the extraneous off-ice developments? We are all shaped by our experiences, and if you end up working your way through the Boston system you are going to meet different people and have different life experiences then if you went through the Toronto system. Don't scoff at these details because these things are in many ways more important to who we are as people than what we do for our occupation.

Without belaboring the issue, these are the things which stand in the way of evaluating a Player-for-picks deal.

Let's simplify things from the Boston perspective and ignore the fact that the Leafs got Kessel. They have to concentrate on the value of those picks outside of the expectations of Phil Kessel with the Toronto Maple Leafs. If these picks bring a missing piece that allows them to compete for - and perhaps win - a cup with in the next X number of years, then by most measures it was a successful trade.

You must do the same from a Leafs perspective. Pretty much ignore those draft picks because I'm pretty sure I have proven that there is no way to measure the value of these picks in any meaningful way. They were assets that we could have used in one way but instead were spent differently. It really comes down to this - what is our expectation of Kessel? I can't answer that for anyone else, but for myself it is this:

I expect him to contribute to the team mostly by his scoring and playmaking ability - I want to see him have 5 healthy seasons with more than 70+ games played each season. I want to see him have productive seasons of 30+ goals. I want to see him help our team make the playoffs and play well in those playoffs... and ultimately I would like to see him be a key piece in any cup run within the next 5 or (depending on a re-upping) more years.

I cannot place expectations on draft picks, so those are dead cards to me. It is time for Boston and Leaf fans to take what they have and try and turn that into positive results for our respective hockey clubs.

Then again, I could be full of it and I am sure you will tell me so in your responses to this post.

Good luck in Toronto, Phil - Hope you didn't take all of those 'one ball' jokes seriously.

Edit: I guess I kinda screwed everyone out of an answer to the question as seen in the headline... so instead I'll throw a poll in here is a fan community that allows members to post their own thoughts and opinions on the Toronto Maple Leafs and hockey in general. These views and thoughts may not be shared by the editor of