I’m going to look at the NHL since my knowledge of SHL trades is pretty limited. As a Habs fan there have definitely been a lot of questionable trades in the history of this team, and I’m sure there are probably some moves that were made a long time ago that were pretty poor. However I will go with the one that immediately popped up when I saw the post: Trading away Mikhail Sergachev to the Lightning in exchange for Jonathan Drouin.

This was a move that had desperation written all over it. I knew from the moment it happened it was an attempt to bring in a francophone player and appease the fans and media more than trying to actually improve the team. I always knew the trade was bad, but what really put the stamp on it was the fact that when it was made, Marc Bergevin said it was to bring in a center (everyone knew Drouin wasn’t a center). Then at the end of the year he openly stated that Drouin wasn’t a center. He obviously knew this and threw away our best prospect for a couple of seasons of a decent Drouin and now he signed in Colorado as a UFA because he was no longer needed and wasn’t producing. Terrible trade from the moment it happened and I couldn’t be happier he’s no longer our GM.