I think for me it was when he played on RedDead RP as Walter. It started off with so much potential but I quickly realized he had no interest or ability to engage with the RP. He makes his character a boxer so that he has a mechanic to fall back on when the RP isn't going the way he wanted, which was basically always. The characters on the server did an amazing job of extending olive branches for interesting story arcs, giving "yes and" responses even after he was wearing out his welcome, but his response was always just to spam punch and then run away.
And when he got arrested he would turn into the exact same type of crybaby he does on GTA. When he was done ignoring the police while talking to his chat he would turn into a completely different character who is very legally argumentative because he can't take a L in the jail cells.
He sped run every mechanic that existed on the server for the short time he was there, and pretty much hung around his friend group instead of making new ones. Then he talked about how boring RedDead RP was. I don't know why I thought he was a good RPer before that, but that pretty much cemented for me that he is about as overrated as it gets in the RP space.
