There are good examples and bad examples. Oilers are a bad example as they have 2 top 5 players in the league, one potentially being a top 5 player all time when he's done his career. A good example that you could've used is Florida finally being a winning cultured team after years of never winning a playoff series. Personally I think it has more to do with team building but counter points to that perspective would be a team like Buffalo or even Ottawa who on paper are teams built to do better but have a culture of losing that they can't shake