Everyone in this story sucks.

As a manager, the people I hired were almost always smarter than me or better than me at various things. That's why i hired them.

I did my best to make sure they were empowered to solve the problems the org needed solving.

Why would I not want their opinions or viewpoints, especially if they differed from my own?

Heck, why would i try to enforce my opinion or viewpoint in the first place?

Not realizing this makes the boss here a crappy manager. Yes, lots of crappy managers exist (for many reasons - one commonly overlooked one being that technicaly knowledge/etc is often shared and discussed much more than manager or organizational knowledge. So it doesn't proliferate as easily and quickly. There are many other reasons, some simpler, some more complex)

Truthfully, I resolved many many more arguments between people (within my own org or between orgs) than between me and someone else.

At the same time, the person arguing with their boss doesn't realize (until much later) their job is not to be technically right. Technically right/good is one of many aspects that are often getting traded off against each other. One thing they seem to not have discussed at all is "is this worth arguing about?". Does this choice really matter? What was the worst thing that happens if they don't do it the way they were arguing about. How likely is that really to happen, and if it does, can you tell early enough to do something about it? etc.

Reading this story feels like someone dragging out an argument continuously that simply didn't need to be argued about at all because it didn't matter enough.

The takeaway isn't that you should avoid arguing with your boss (as others say, you should run away from bosses you can't disagree with). The takeaway is that you should stop and think about whether this is really an argument that needs to be had, instead of arguing about everything because it's not perfect.

Never been a manager, but there comes a point when you realize that you do not have the full picture as a subordinate. Your boss isn’t just managing you. They have a whole team to coordinate with and against the priorities of the rest of the business to stay on track. If you’re not helping them and are even making more work, it will not help your career.

No, boss -- you suck.

See what I did there?