Good question, he probably had the school principal on his list of people he would $hit on after achieving hero status in Boston. Think about it, he was on TV as a teenager and his life has been rubbish ever since. Every time he tried to show people he was a big shot he got pummeled.
"But I was on TV so I know everything about the entertainment industry, you should hire me as the boss of this place!"
A: I don't think so buddy, you'll start as a substitute wedding DJ and work your way up, if you're lucky"
"But I'm also cool and famous Cecily, remember me?"
A: Yeah yeah, sure sure I remember you...
After Boston:
"You can't just send me letters about my kids' absence, don't you know who I am now? I'll destroy you on FOX!