As a moderator on a minecraft server (the type of game matters little), several times I had to deal with what I call "cocky passive-agressive borderline trolls": usually a smart, young user, that irritates everyone with passive-agressive behaviour, teasing and provoking, managing to remain borderline within the chat rules, but annoying the hell out of most people.
So within the server rules, they did not break them, and it is difficult to pinpoint any fault within their chat logs without looking at the big picture and adding up the reactions of other players to their presence.
They are usually nice to their posse only, and most like to target server staff with their annoying behaviour. When threatened they back off very quickly, and start a "i did nothing wrong by the rules", usually refraining from trolling for some time (a couple hours, or until the most stern staff member logs off).
I've seem good, nice players driven away from the server because they can't stand these trolls.
What can be done to deal with this kind of player? They are sleazy and smart, and usually act borderline and using innuendo, so it is hard to mount a case on them. Even the ones that do not quit usually contact us on skype to vent their frustration and anger at being trolled and/or witness the trolling.
What can be done to deal with these types?
Differs from How do I deal with online trolling/harassment in video games? because it is from chat moderator point of view.