Phil Kessel - The Toronto Side And Why Boston Loses

"That plane to Toronto's leaving, and if you're not on it, you'll regret it. Maybe not now, but soon, and for the rest of your life." Brian Burke, to Wade Arnott, Phil Kessel's agent.

Okay, we made that exchange up. What is true is that Phil Kessel was traded for three draft picks - a 1st in 2010, a 2nd in 2010, and a 1st in 2011. This seems insane, and is insanely complicated, so we're going to examine it in two posts - this one looks at why Toronto 'won' the deal and Boston lost it. So, without further ado:

The 2010 Draft Is Weak

We fully admit we don't keep up on draft classes - in fact, the reason we don't is because when we were young, we were taught that the 1999 draft class was exceptionally strong, only to have it turn out to be one of the weakest in NHL history. However, if the 2010 draft is weak in the way that the 1996, 1999, 2001, and 2007 drafts were weak, a 1st round pick that will likely be in the range between 10th overall and 20th overall does not have a great deal of value. 1st round picks are exceedingly valuable when they might render players that provide excessive cap savings in Year 3 of their entry-level contract - weaker players obviously provide less value, but they also take longer to reach the NHL.

Brian Burke Has a Boatload Of Assets

Toronto has NINE UFA Players. NINE. (Imagine this as Principal Rooney in Ferris Bueller's Day Off). None are particularly valuable besides Alexei Ponikarovsky, but we theorize their value may be like this at the deadline:

Alexei Ponikarovsky - 2nd and 5th
Lee Stempniak - 3rd
Mike Van Ryn - 3rd (perhaps 2nd)
Matt Stajan - 3rd
Garnet Exelby - 3rd (or 4th)

Now, Toronto may have no interest in trading these players at the deadline, especially if it is in the playoff race. However, it shows that Burke is capable of recouping some of the assets he lost.

UFAs Are Expensive And Don't Exist

Phil Kessel is a 'pure scorer', possibly in the elite. Let us look at the list of elite UFA 'pure scorers' coming available in the next 3 seasons:

Ilya Kovalchuk

Gambling that Ilya Kovalchuk comes available and wants to sign for a penny less than what Marian Gaborik received is a fool's wish. Kovalchuk would likely command $8+ million - if the salary cap falls, there are not many teams that can afford that. Plus there is always the worry that Ilya Kovalchuk returns to Russia.

You Have To Choose What Year You Will Contend

Besides out-of-nowhere success of the sort the Bruins had this past season, under the salary cap one has to judge which years they think they can be a Stanley Cup contender and plan accordingly for that season. The Leafs must be circling 2012-13 - all of their onerous contracts (Blake, Finger) will have ended. Nazem Kadri's contract may slide to begin in 2010-11 - this puts that all-important 3rd year of his entry-level contract right there. 2011-12 may also be important - Luke Schenn is not arbitration-eligible that year, and Burke may be able to bury the Finger and Blake contracts in the minors if he so chooses.

Toronto Has Shown They Can Attract Undrafted Talent

The NHL draft isn't the only place to acquire cheap contracts - undrafted free agents are important as well. With the Leafs signing 3 of these this past season, they clearly think they are running the kind of organization that makes players want to sign up. New Jersey has certainly made up for draft mistakes by sprinkling their lineup with undrafted free agents - Toronto will look to do so as well.

Why Didn't Burke Sign Kessel To An Offer Sheet?

Simple - Boston might've matched. And if the number was made high enough that Boston wouldn't match, the cap savings that Kessel provides are gone. Furthermore, Kessel may have refused to report to Boston if they matched, causing all sorts of problems.

Why Boston Lost

These draft picks are not quite lead balloons, but they are certainly far less valuable than prospects at this juncture. Two of the picks are in a weak draft. Plus, Boston was a legitimate Stanley Cup contender if they could've shoehorned Kessel on to their squad - they may be missing their window of Stanley Cup contention. They gain cap relief, but they also squandered money on the Derek Morris contract and buying out Peter Schaefer - these moves should not have been made before securing Kessel's contract.

Coming Soon: The Boston Side and Why Toronto Lost