Grate n Colorful Oz
The Hutson Hawk
Right off the top of my head, Edmonton is a warning. Years of first overall picks and years of agony.
They have a couple players that you can't miss with, but they can't shake the mediocrity.
The issue is that some people assume its enough to just keep losing and build up talent to eventually win the cup. It's not as simple as that.
Edmonton is a bad example. If it weren't for Klefbom's career ending injury, they never would've needed to sign Nurse for so much and would have both of them and might've had a final or a cup already.