Especially then, because if that's the case then you know there's more to this story than just what you're experiencing in that moment.

Exactly.

If you're arguing with your boss's boss's boss, who has worked at the company for five years and the industry for two decades, and you think you've unraveled their entire argument by reading a few blog posts, you're wrong approaching 100% of the time. Best case scenario is that you've missed something specific to your company, or industry, or the current technical implementation, or some obscure contract the previous CTO signed that they're still trying to get out of.

Or possibly you're extremely in the right but they have an ego the size of the moon and they will punish you if you bruise it.

Either way you lose.

Not to just reframe AnimalMuppet's point, but which of these two things is more likely?

1) Your couple hours of research has uncovered something blatantly obvious that was somehow missed by the other party.

2) Your couple hours of research hasn't shown you some edge case or something that is common knowledge once you've been in the field for 2+ decades.

I'm not saying #1 never happens, only that #2 is much more likely. It's a horses vs. zebras argument.

3) The other party has a lot of stuff on his/her plate and does not get the luxury to spend hours of research/thought on architectural details.

And don't forget "Hasn't actually worked hands on with anything you're doing for a decade"

In pc86's scenario, though, it's much more likely that you're the one with the ego, thinking that reading a few blog posts makes you more informed than a 20-year industry vet.

How often is "something more to the story" solid technical reasons vs something like kickbacks and bribes?

2+2 = 5 situations.

In my experience it's rarely (read: never) that clear, is my point. When it's that "obviously" wrong, there's almost certainly something you don't understand.

the important word is "openly"

More like when you've been at the company for about 3 weeks

What about the inverse? The CTO is the new person in my situation.