Apologies for taking so long to respond to this. You raise some excellent questions (and thanks for the props!).
You know how I see it? I see Jon's (and similarly, Chris's) mind as a kind of snowglobe within a polarized mirror. Others can see in, Jon can't see out. The area around him, the one he's spent most of his life in, is the only area of the world that he's familiar with, and even then, there are limitations within that world. Certainly, other places exist - they're forced into his perspective when he went to ASU, for example - but, for the most part, Jon's limited capacity can only see what is around him, what is familiar to him, what makes sense to him.
Now you would think that inside this little bubble, Sweet would be comfortable. But there's a catch: Other people walk in and out of it all the time. Likely, the majority of these people have nothing to do with Sweet, except for his parents, family, bullies, teachers, and authority figures. Meanwhile, other people have parties, friendships, lovers, sex, admirers, shoulders to cry on, etc. And none of these folks are the least bit concerned about Jon Sweet.
This leaves Jon at a disadvantage. He is the king of the world due to his myopia ("The media should be coming to me! I'm the story!"), but no one acknowledges his royalty. What's more, nothing Jon does has any effect in this world. He is either ignored or gets in trouble. Additionally, he's a coward who's afraid of getting hurt. Heck, he backed away from a threat of beating and strangling you when you suggested he "bring it on," after a fashion. I mean, really, you never even threatened him, you simply made it clear that he was not to talk to you in that manner, and he shut down immediately. Jon failed at being an internet tough guy.
Okay, so, what do you do when you're the king of the world, but no one will bow down to you? You do the same thing that venerated scientists do when questioned about the nature of the world around us: make theories. Of course, professional scientists base their theories around observation. Jon does the same, but his observation is skewed due to mental problems and a desperate emotional need to make himself relevant in a world that couldn't care less about him.
Nobody cared about Jon back in college, save for one adviser [?] that pushed him to join The Herald. Afterward, the status of fucks given about him remained unchanged (none or fewer). He was tolerated at best, having to go so far as to deliberately attract negative attention to himself (the neck-cracking and peanut chewing).
Jon was, simply put, a hairy, feces-caked asshole, on top of being a Neanderthal weirdo. No one hung out with him, no one liked him, no one praised him. So, looking for sense in a world that made no sense to him, looking for importance in a world that overlooked him, and looking for power in a world that granted him only charity, Jon had to find a way to make himself both relevant and powerful, one that fit inside the tiny, frosted glass of his bubble. Jon saw himself as an outsider who spoke the truth, who ruffled the feathers of the complacent sheep (y'know, those flight-capable sheep with feathers) and cowed PC weaklings too afraid to face the music.
In short, Jon became "The Badboy of College Journalism."
Remember, this was the 90s. The envelope pushed by Madonna, the cast of Saturday Night Live, and Porky's in the 1980s had finally ripped open. The shock jock, the angry pundit, and the outrageous comedian, while nothing new, were suddenly thrust into the limelight. Whether these people told it like it was, or just roused the rabble was unimportant. They were loud, lewd, and lucrative, and they set the media world on fire. There were a lot of angry voices complaining about these people, and a lot of those voices were coming from the left (a lot of the material that these personalities would use often targeted gays, women, and blacks).
Jon wanted - needed - to fit in somewhere. He needed to be someone important, and the fact that he wasn't attractive, or smart, or good looking, or insightful, or physically presentable in any form, or popular, or tolerable to look at without vomiting, or in tune with any kind of rational readership, coupled with the fact that his face was constructed entirely of cartilage and hideous, made fitting in nearly impossible. So, he had to find a way to compensate for this societal rejection. I mean, dealing with it in a mature manner and facing his flaws was about as likely as him dispensing his urine in the proper receptacle. So he thought to emulate his heroes in order to turn his failures into successes, and the Badboy fantasy was born.
That's my take on it, anyhow.
e. Thanks to NobleGreyHorse for the grammar suggestions!