If we go back to 2006 (pre-Katz, I know) to span the whole "Thirteen Years of Thirst", the double-whammy of the Pronger debacle and the Pisani multi-billion dollar contract first made me question the ORG's sanity. Kevin Lowe's battle with Brian Burke and subsequent Penner-signing were highly insane.
The firing of Krueger was incredible. That's one of those things where the ORG needed to put a limit on MacT in his first 15 minutes as GM. (I don't fault them so much for getting Eakins, who was a hot coaching prospect at the time, but it was a perfect storm of wrong-coach-wrong-team.) The Oilers' franchise, win or lose, had always been associated with class (Pocklington in later years aside), but the firing of Krueger by Skype put an end to that...
I didn't mind so much that Taylor Hall was traded. I think it's clear that there was some sort of locker-room problem around then, and whether Hall was part of that or not (I have no idea and neither do you), it seems clear that the team in general wanted to make a statement and establish a new direction, which wasn't necessarily a bad idea. I admit my bias here, because I never really liked Hall though he was a very talented player. Anyway, getting rid of Hall when they then had a core of McDavid, RNH, Draisaitl, and Eberle was at least a reasonable option if they gotten fair trade value. I quite like Larsson and I think at some point (hopefully next season) we'll see him back to his full potential again, but -- to state the obvious -- the Oilers only got about 40% of what they should have got for Hall. (We should be careful not to over-rate Hall, though... he has put in 1 good season in 3 in Jersey.)
The Lucic signing is similar to the Hall thing -- not necessarily a bad idea in principle, but when a guy is clearly trending downward, what idiot signs him long-term at 7 billion dollars a year or whatever...?
Even though Larsson has underperformed for two years and Lucic was a write-off, the Oilers should not have been crippled by those moves... but they were, because the ORG failed to address the glaringly obvious lack of talent on both wings (making Larsson seem expendable) and because Lucic earns more than Bill Gates, thus destroying the Cap.
Anyway, I'm so tired of dwelling on the Oilers' failings of the past 13 years that I'm just going to be positive from now on.