There wasn't really a "moment" when I realized it. Just a gradually building frustration with him and everything he does. Just some examples

• Whenever there's a problem (especially one he caused), he will literally say "not my problem" and/or "not my fault"

• He constantly starts arguments, just for the sake of arguing and causing stress

• There was a period where he'd let everyone know he is an atheist.

• He's always the victim

• Has absolutely no concept of manners. Literally said that they're a pointless construct of human civilization.

• Massive hypocrite

• Does not stop pushing his perverted furry shit on people

• Frequently does mean things and then frames them as jokes, and then proceeds to ask why you can't take jokes

• Can't take jokes himself

• Throws other people under the bus to save his own ass

• He has a counter argument for every argument he has used against you in one of his forced pointless arguments. Refuses to accept this when it's pointed out.

I have to keep being this asshole's friend until high school ends. Drama with him will be far worse than being a fake friend for another year. He used to be a good person.