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LANA!!!!!
Stan Bowman definitely. The speed and agility with which he retooled after 2010 was astounding. Everyone, myself included, predicted the end after 2010. So many cap problems, how are they going to deal with it. But he did and how.
I bet in a few years, Nill and Yzerman.
Yzerman made some big moves last year during the season and during this last off season. Traded away Conacher, got himself a real goalie, Filppula, bought out Lecavlier, fired his coach and brought in Tampa's AHL coach (Who the Griffins and Blashill beat in the finals). They're doing way better than us that's for sure.
Just looking over Holland's record over the past 5 years is sad. Other than the gimmes, he's made *very* few good moves. Any GM can extend Datsyuk. Any GM can sign Hossa. Any GM can sign the homegrown defenseman who loved the Wings his whole life and has ties to the organization.
And while some of the moves are only bad in hindsight, sooner or later you have to ask: Why does most of his moves turn out badly? Even if we can't fault him for a single decision alone, cumulatively, his decisions are a net negative for the team.
Chiarelli in Boston has done a great job over the last handful of seasons. Nice FA signings, drafted pretty well, swung some major trades- dude's got some stones.
Sure, he's struck out on a few moves but he's won way more than he's lost. Not being afraid to make a major move seems to be key.