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First one that came to mind was Roberto Luongo's 12 year, $64 million contract. Mike Gillis ended up trading Cory Schneider away before he could find another team to take that Luongo contract. And Vancouver had to retain part of Luongo's salary to make the trade happen. I think Luongo ended up retiring while still having 3 years left on the contract. I guess the silver lining is that Luongo remained relatively good before he got traded.
I think the hang up on Luongo was he sucked in the playoffs. He was still a pretty good goalie otherwise. That definitely was a ridiculous deal at the time.
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Yea, he wasn't very consistent in the playoffs, especially towards the last few seasons with the Canucks. Still great goalie and great career though. I think NHL goalie with 2nd most games played behind Brodeur and 4th most wins behind Brodeur, Fleury, and Roy. And of course HHOF 2022.
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