Despite having arguably the best player in the world at their disposal in captain
Connor McDavid, the Oilers have failed to achieve any true playoffs success, and there's no doubt that changes must be made to avoid wasting McDavid's prime years in the NHL. You can't blame current Oilers general manager Ken Holland for the team's lack of success; Holland has had very little cap space to work with since joining the team, and inherited a number of bad contracts from former Oilers general manager Peter Chiarelli, but this upcoming offseason could be when Holland truly leaves his mark on the team.