What is the single worst decision your team ever made?

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The Kings have pissed away the draft picks that ended up being Reggie Leach, Ray Bourque, Phil Housley, Tom Barrasso, Claude Lemieux, Trent Yawney, Brian Willsie, Robert Esche, Martin Skoula, Todd Fedoruk, Brayden McNabb, Tyler Myers, Jake Gardiner, Ben Chiarot, Braden Holtby, Oscar Klerbom, Nick Bjugstad, and Jason Zucker off the top of my head. I know the Kings probably wouldn’t have drafted all of these guys but it’s always heartbreaking to think about.
 
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For the Sens, drafting Brian Lee over Anze Kopitar.

Kopitar had 65 points in 2006-2007, so if the Sens had him they probably would have beaten Anaheim in the Finals.
 
2017 draft is also something that stings pretty badly. Heiskanen, Makar & Pettersson as 3,4 & 5th picks.
That certainly hurts, but for all they’re great players, I don’t know that the team would have been able to capitalize on the right call there the way we could have on Lindros/Forsberg/Brind’Amour down the center in the mid-90s, or adding Cujo in net to the roster that had just won the ECF the year before. I just don’t trust our current player development to have turned those three into who they became elsewhere.
 
You forgot about
Or this...
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Devils: Getting rid of Lou Lamoriello

Literally set the franchise back so many years. We proceeded to be a bottom dweller for the next 10 years with only 1 playoff appearance (and a first round loss at that). We lucked out by getting the first overall twice with Hischier and Hughes but the reality is that Lou continued his success with other franchises without missing the playoffs.
What?! Lou and Vanderbeek left the franchise in a husk with all the bad drafting and horrible money management. The franchise was set back so many years because of Lou.
 
The 2015 NHL Draft for Boston stands out for me.
It absolutely hurt, although Debrusk and Carlo made it hurt a little less lately.

How Sweeney makes moves like drafting McAvoy and getting Lindholm for peanuts but then reaching for Senyshen blows my mind.

Zboril you can't hate on as much as he was drafted near where he was supposed to.

Senyshen is such a mind boggling weird pick
 
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For Calgary, I'm torn on letting Martin St. Louis walk as a UFA, or trading up to take Trevor Kidd. With one of the picks that Calgary traded away to move up, New Jersey picked Martin Brodeur.

There's some pretty bad trades (Gilmour, Phaneuf, Roberts' rights) but none of the trades compare to those two franchise altering blunders.
 
Probably trading Gretzky. Still won another cup but would have won more well into the 90’s if they kept that team together.
 
Benning is obvious answer but ill go with Drafting bourdon over Kopitar. Probably win the cup at some point with Sedin Kesler and Kopitar down the middle. Also would've kept him from a main rival in those contending years. I also think if we draft Kopitar that Gillis doesn't get fired and Benning never gets the opportunity to nuke this franchise.
 
I was going to say trading Roy, but your right. The Roy return was bad, but the way that championship team was systematically dismantled was worse.
Even if that trade happens, it would have been better handled by Savard/Demers OR any person with reasonable experience. I wasn't opposed to moving him in general.

It's not like there weren't rumours from early in the 90s that involved trading Roy. One was a one-for-one deal for Yzerman.

Under Demers things had become a country club. Corey wanted to clean house and tighten things up. Roy was seen as the ringleader. Tremblay thought, "if I can break him I'll control the room." That's what the 9-1 drubbing was all about.

Fine. Trade him. But not for quantity over quality - even if the pieces were well thought of at the time. And for heaven's sake don't take a young goalie back in the deal. Thibault was destined to crack under the pressure of trying to replace Roy. Do a superstar for superstar deal. Let him sit until you find the right one. Get your goalie in another deal.

Whole thing was a series of examples of what NOT to do.
 
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