The problem is I think this forum underestimates Staples.
Staples to me isn't some die hard oiler fan crushed each year the oilers
loose. In my best estimate:
Staples is a Rudy Giuliani. Rudy takes a crushing fair election and spins it to enrich himself (i.e.
https://rudygiulianics.com/). Rudy predicts Trump will win the election by large margins and then when they
loose, he makes the election sound "rigged" and unfair after previously predicting. He doesn't believe in this, he is enriching himself with messaging.
Staples follows the same playbook, duping oil fans as Rudy dupes MEGA supporters. Year after year Staples writes how the Oilers are a powerhouse at the start of the year, and then when the year ends, writes about how this or that didn't go their way but did for other teams so that's why the oilers lost. He hardly (or never) looks at the systemic problems the oilers have, but finds excuses for the fan base to buy.
Staples knows his role to make money in life is the same as Rudy is currently - lie to your fanbase and have them comeback to you to find the answers of whom to blame on crushing defeats. I am not hockey writer, so to avoid a slander issue, I will say this is my uneducated view of his columns from reading what is posted here, which may not give him a fair shake.
In short, in my view, Staples is the Edmonton version of Rudy. He knows better, and isn't devastated when the oilers
loose- in fact, I would be he is gleeful about future income.