@cherry89,
Stand your ground on the second email and don't send it. Yeah, give him a pleasant greeting if you run across him, and maybe see how he reacts.
By the way, I have a gmail address that I set up for one annoying individual to forward his political crap to. I check it maybe once every two months. I doubt this is his situation, and I'm not making excuses for him. Just considering unlikely but possible situations.