I was on the imperial side. He serves no purpose anymore, and I'm sick of not being able to stop his racist tendencies. Why not take off the essential flag when an npc isn't useful anymore? He doesn't even act like the civil war is over. His entire presence is annoying. Why would Bethesda let him stay essential? Is there a quest I haven't done yet?

You mean Rolff? I think you have to pickpocket something from him as one of the thieves' guild radiant quests. I just steal all his clothes and kill his buddy.

Can I kill him after that? If so why not?

blame bethesda for the essential tag. I just hope we get to punch his ass out later on in the game, like a daily quest or soemthing.

Put a bucket on his head so he's blind foooreverrr!!!! Muahahahahahaha!!

'Cause you need to be able to brawl with him. Skyrim depended on essential tags on many questlines that it's silly. You must remove every essential tag very carefully (by careful I mean one by one you check every quest they involved in) if you want to make a realistic gameplay without getting a swarm of bugs.

I brawled with him. I always do. So if I do the thieves guild thing he'll die? Does this apply to all characters? I know the stormcloak captains never die

He'll probably remain essential.

Personally I am off the extremely unorthodox adventurer view that being annoying, even being an annoying racist isn't enough cause for killing someone.
Yeah, imagine that.
He is a bully, but not a real threat.

I never kill Heimskr in Whiterun.
I never tried to kill the Adoring Fan in Oblivion or Sticky in Fallout 3.
I am totally weird like that.

When roleplaying I need a cause to fight and to kill.
Self defense, protecting others, quests for good chars.
For evil/insane chars the motive ranges from quests, assasination targets, psychotic murderous urges, they have something I need or want such as blood, souls, loot, gold, a very nice hat(True story, Shivering isles), because it is funny or because I felt like it.

Rolf pushes me, but mostly because he implies that he'll [censored] the Dunmer woman you meet when you first enter the city. Other than that, I've never been tempted to murder anyone (except maybe the Black-Briars besides Ingun) so I could take over their business and rule Riften myself (on my characters of more questionable morality).

However, I do mess with Rolf. Using the Fortify Restoration Glitch I make incredibly powerful poisons of either Paralysis or Fear and slip them to him so he ends up either collapsing in the street for days or running around screaming in terror.

My reasoning for killing him is because my character thinks he's racist, he thinks he's better than her, insults her in her face, implies she wants to [censored] the dunmer girl, and says he wants to through all dark elves and argonians into a pit and let them kill each other. Also, my character is used to getting away with things because she was a noble in hammerfell, so killing Rolf is a no-brainer to her. He's just insufferable, even moreso that bethesda makes a character they know everyone will hate, and make it impossible to make him go away no matter what.

That's a good one

I don't kill annoying people, either. I try avoid them. Rolff's an idiot, but killing him would make me no better than him. I would like to send him on a trip to Morrowind, though

It still bothers me that in a game where you can apperently "do what you want" you cant do such a basic thing for no apperant reason. I wish he could at least go away somehow, or maybe even have some character development? He doesnt even respond to Ulfric being dead, and he always stays a jerk. He just stagnates like every other npc, but his locked-in personality is so aggrivating that it exaserbates this issue. If I could just kill him I could deal with it.