Until Holland the Oilers were doing terribly, that's no secret. As
@TheNumber4 said, we were dead last for a reason... there was zero depth around Hall/Nuge etc. And Chiarelli's shortcuts (Lucic, Sekera both signed and bought out) plus our best young defenseman (Klefbom) retiring at 26 years old, and our 2nd best young defenseman Larsson (and return for Hall) leaving out of loneliness (and replaced by frickin Ceci) were killer blows to the first 5 years.
So yeah... we missed that first window you get when you've got elite young talent on ELC. Blackhawks got two during this period. You guys only got the one.
But then things get tough right? You don't remember? For SIX YEARS you guys could barely get out of the first round. Why? You couldn't afford to keep any of your depth after signing both Crosby and Malkin to 31% of the cap.
But you had a huge advantage right? More or less every year, the cap was rising for you. By the time you won your next cup in 2016 the cap had gone from $56M to $71M. That's a 27% rise in the cap.
As for the Oilers:
1) We've already established they blew it (prior management) for McDrai's ELC
2) While the cap was rising by 27% during Crosby & Malkin's prime, it still didn't help you until they were both nearly 30 years old. Meanwhile, for the last six years (this year excluded) the Oilers dealt with a cap that went from $79.5 to 83.5M for a rise of 5%. Do you see the difference?
3) When you won your 2nd cup, Crosby and Malkin were on their 3rd contracts, making collectively only 25% of the cap. Malkin was about to turn 30. Crosby about to turn 29.
This year, Draisaitl is 29, still on his 2nd contract. McD is 27, turning 28, still on his 2nd contract. And since the cap finally rose appreciably for the first time in 6 seasons, they collectively are only making 23% of the cap.... and guess what, just like Pittsburgh we've finally been able to hold onto (Henrique, Brown, Perry) and add some (Arvidsson, Skinner) depth... despite some casualties (Broberg, Holloway).
Just like Pittsburgh, we went to the finals last year lost by one goal in game 7... if we win this year, McDrai will be a year younger than Malkin/Crosby when they won their 2nd.
Other than the earlier cup missed... I don't see how the Oilers are trending any differently than Pittsburgh, despite playing in a much tougher macro-economic environment.
He's going to be a legend the rest of his life regardless. You can enjoy him with the rest of us in the 4 nations cup.