To add another twist to this exercise, I also think it is important to consider the contract vs contention window for a team.
For instance, I don't think the Lucic deal ranks in the top 5 - maybe not even in the top 10 worst deals any longer due to the length, cap-hit, and usability of the player. However, I wonder where it ranks among teams who are in the 'win now' mode. If Lucic's cap hit wasn't on this team, they could have added something significant to their top 6, and probably had the wiggle room to have re-signed Brodie.
Doughty, Karlsson, Burns, Vlasic (yikes!), etc - they all have terrible deals, and it will only get worse. However, they are on rebuilding teams (for now - those are lengthy deals and you would think that their respective teams will be contending again at some point during their contracts).
I wonder which contracts around the league are crippling their organizations at the moment. Florida is wasting the prime years of some very good players, but they don't really seem to be a competing team. Although they are not a cap team, they have an internal budget and of course paying Bobrovsky 10 million a year is going to eat into that internal cap. Is he stopping them from competing? Maybe. If so, then he is the worst deal in the NHL.
I wonder which of the bad contracts around the NHL are hurting a team from competing the most, thus making it 'the worst deal'. I think Karlsson's deal will eventually be the undisputed worst deal in the NHL within a few seasons, as it seems he is slowing down (and has an injury history).
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