By 'knows where to hit someone where it hurts' I mean someone who uses another person's weaknesses and feelings to their advantage. Say if their opponent had low self esteem about a certain part of their body the person would make sure to bring it up in the argument to weaken their opponent.

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    Sounds like a shrewd person. But really, for single word requests, you need to give an example sentence with a blank where this word would go. You may want to take a site tour too. Welcome to ELU.SE, by the way. – alwayslearning Feb 19 '17 at 5:41
  • A psychopath would do this but I'm not sure if that's specific enough. – Chris M Feb 19 '17 at 6:15
  • If the person is able to find their opponents weaknesses, then as alwayslearning says, they are shrewd, or cunning. If they are willing to use their opponents weaknesses, then they are ruthless, merciless or one of the many synonyms. – JonLarby Feb 19 '17 at 21:49
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    Button pusher. – aparente001 Feb 20 '17 at 4:40
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    ......*Sadist.* – aparente001 Feb 23 '17 at 6:42

You can try the word "gaslighter":

Gaslighting is a tactic in which a person or entity, in order to gain more power, makes a victim question their reality. It works much better than you may think. Anyone is susceptible to gaslighting, and it is a common technique of abusers, dictators, narcissists, and cult leaders. It is done slowly, so the victim doesn't realize how much they've been brainwashed.

and a gaslighter is:

One who engages in the psychological tactic of gaslighting.

If online, you can use the word "griefer":

A griefer is a player in a multiplayer video game who deliberately irritates and angers other players within the game, often using aspects of the game in unintended ways. A griefer derives pleasure primarily or exclusively from the act of annoying other users, and as such is a particular nuisance in online gaming communities, since griefers often cannot be deterred by penalties related to in-game goals.

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