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There is only one goal
Love the trades or hate the trades? Phil Kessel, yes or no? Brian Burke has been building the team for the long term. He has had spurts of "this player will help us right now..." but he is creating a team to make a run at the Cup every year for a long time.
To do that you have to build depth through the entire organization, through management, coaching and player personnel. Everyone from the owners, to the building crew, to the associate trainer and the minor league system all need to be working toward the same consistent goal.
It is hard to think of a trade or a signing where you say "Leafs lose" on that deal.
Even the Phil Kessel trade looks like a win. Kessel is a 23-year-old sniper on the verge of breaking 50 goals. And when he does, he will be a 40- or 50-goal scorer for 10 years.
Last year, Kessel scored 32 goals and 32 assists for 64 points. Last year, Tyler Seguin scored 11 goals and 11 assists for 22 points.
Granted, in five years, Seguin might be the better player—but who knows for sure. If Lord Stanley is going to be raised, a Phil Kessel-like player is necessary.
Throughout each year, Burke has been making every position stronger and deeper. This consistent approach will eventually produce championship teams.