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Before going to your playoff draft, fill out a bracket with your personal predictions. When you get to the draft, try to build your team around one of the teams you have going to the Stanley Cup finals.
The reason is by putting all your eggs in one basket, you're virtually guaranteed to win the pool if that team does make the finals because you'll have most of the scorers on that team.
If your pool has goalies, pick the goalie from the team of your NHL bracket, even if he isn't the best goalie available. If you take a goalie from a different team and the team you've selected many players from is eliminated, the other goalie won't help you win anyway, but the goalie from you're team will further ensure victory.
For example, each of the last three seasons I've picked Detroit to come out of the Western Conference. I've picked around sixth out of 13 people and I've always ended up with Pavel Datsyuk or Henrik Zetterberg in the first round.
After that, I picked Johan Franzen in the second round, and followed him up with an assortment of Nick Lidstrom, Brian Rafalski, Marian Hossa (2009), Tomas Holmstrom, Valtteri Filppula and others in the next five or six rounds. Toward the end of draft, I picked depth guys like Brett Lebda and Jonathan Ericsson.
Unfortunately, I lost last season, when the Red Wings were eliminated in the second round, but I won in 2008 and 2009 when they reached the Cup finals.
This season, I'd recommend this strategy if you are picking anywhere outside the top three picks.