Ken Holland inherited a team that was wading-pool deep and cap f***ed to Tuesday. A team that missed the playoffs twice in a row. A team that would immediately lose its under-priced top defenseman to a career-ending injury at 28 years old, which would put them into LTIR for four years. A team that based its top contracts around the idea of the cap going up, only for a pandemic to induce a three-year flat cap. A team that already had the challenge of being the Edmonton Oilers. And he's done a very good job with it despite all that IMO.
The Oilers have gone from a team that was pushing Ty Rattie and Alex Chiasson in the top six to a team that has Kane, Nuge, Hyman and Brown on a collective AAV of 16.5M dollars. It's the best top-six group in the league and they just put up one of the highest-scoring seasons in modern NHL history. Their bottom six, still a work in progress, just finished the year with 10+ goals each. At the time he started, it could politely be described as a group of non-NHL players.
The Oilers are identifying pro players far better than they have in decades. They're developing later picks into actual, promising young players. I don't think the Oilers have been a more functional organization since the 1980s. Seriously.
"The Oilers aren't good enough" Yes, they are. They've lost to a Colorado team at the height of their possible power which immediately lost half of its forward depth to the cap. They lost to a Vegas team running a 96M dollar roster (and gave it a better fight than anyone), and even that series turned on a goalie injury and a hot back-up.
No team is without flaws on July 1 in a flat cap. The Knights gave away Reilly Smith for nothing just to become cap compliant. Boston just lost so much talent. Toronto shuffled Bunting, O'Reilly and Holl for Bertuzzi, Domi and Klingberg. Tampa had to let Killorn walk. Florida replaced Gudas with Ekman-Larsson. Colorado added two players with negative contracts in order to rebuild some of its depth semi-affordably. The Wild are the same team pretty much completely. *THESE ARE THE OTHER GOOD TEAMS*
These are the good times. You can say "should have won the Cup" or "the Cup is the only success". I get it, I do, but you're calling a B+ job an F because it isn't an A and you're missing the good times. The times when we know the Oilers go into a season as maybe one of seven teams most people wouldn't blink at winning the Cup. The times where the Oilers make the playoffs with home ice advantage for 4 straight years. The times where the Oilers have their handcuffs off at the deadline.