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Authority should be questioned, again and again and again. Not in order to be an asshole but because of the consequences when we don't:

1. scope creep. They will slowly become more authoritarian over time: (legitimate) authority in one area will bleed into (illegitimate) authority in another area.

2. they will be unable to deal with defiance. Because they're not used to it and because to much of their identity is intertwined with their professional authority.

There are too many people out there who enjoy exercising their power over others. Too many teachers who completely lose it when students pull some harmless prank. Too many police officers who threaten violence when talked to disrespectfully. The victims of overreaching authority are always -- as the article points out -- the weaker members of society. Standing idly by in the face of injustice is not the mature adult thing to do; it's plain cowardice.

All authority should be assumed to be illegitimate, and structures of authority that cannot justify their existence must be dismantled.

Authority should be questioned, again and again and again.

Why should I?

(Old school PLIF ref :) https://imgur.com/LBrFO )

>But though I was initially disappointed at being categorized as an extremist, as I continued to think about the matter I gradually gained a measure of satisfaction from the label. Was not Jesus an extremist for love: "Love your enemies, bless them that curse you, do good to them that hate you, and pray for them which despitefully use you, and persecute you." Was not Amos an extremist for justice: "Let justice roll down like waters and righteousness like an ever flowing stream." Was not Paul an extremist for the Christian gospel: "I bear in my body the marks of the Lord Jesus." Was not Martin Luther an extremist: "Here I stand; I cannot do otherwise, so help me God." And John Bunyan: "I will stay in jail to the end of my days before I make a butchery of my conscience." And Abraham Lincoln: "This nation cannot survive half slave and half free." And Thomas Jefferson: "We hold these truths to be self evident, that all men are created equal . . ." So the question is not whether we will be extremists, but what kind of extremists we will be. Will we be extremists for hate or for love? Will we be extremists for the preservation of injustice or for the extension of justice?

-MLK, Letter From a Birmingham Jail

There is defiance and then there is just being an asshole. I think we should appreciate the difference.
They're not on the same spectrum. An asshole being justly defiant is not comparable to a nice person being unjustly compliant.

Put it this way: Many people who history currently regards as being "correct" were assholes, and many people who history currently regards as being despots were wonderfully charming and pleasant.

Also, the view of these people over the course of history has changed (due to many things, some ranging from societal change of opinion to historical revisionism).

As stated in the article: "Cartwright described a related psychiatric disease, dysaesthesia aethiopica, that he said was ‘the natural offspring of negro liberty – the liberty to be idle, to wallow in filth, and to indulge in improper food and drinks’. It’s easy to roll our eyes at such shoddy logic and obvious racism. But to many Southern whites, Cartwright’s explanations made perfect sense. They were used to justify both the murder of slaves and the recapture of runaways."

Was Cartwright being an asshole? Or were the slaves trying to escape being assholes? Any person's opinion is unfortunately defined by personal circumstance, society, and interest.

I'm pretty sure that James F. Blake thought Rosa Parks was just being "an asshole".

The two are not even in the same league: being an asshole is to demand from other individuals the very liberties that you deny them. Being defiant is to resist how social norms and conventions are applied to you.

I am reminded of this quote from G.B. Shaw: "The reasonable man adapts himself to the conditions that surround him... The unreasonable man adapts surrounding conditions to himself. All progress therefore depends on the unreasonable man."