When it comes to shows that have made a name for themselves on the dicey side of political correctness, South Park absolutely takes the cake. But the creators took mocking PC culture to new levels when they introduced PC Principal, a caricature of that same culture. Even though the courage of his convictions fueled PC Principal, Jimmy was the one person he simply could not handle. And South Park's resident comedian gave him a run for his money.
PC Principal made his debut in Season 19, Episode 1, suddenly replacing Principal Victoria who had been with the series since the beginning. Reputedly, he was supposed to be a one-off character .that died at the end of that same episode. But Matt Stone and Trey Parker apparently decided that he had a brighter future than that and declared the new guy needed to hang around a bit longer. That was the right call as he's become an incredible character
As his name would suggest, PC Principal has completely devoted his life to promoting and defending political correctness. At the same time, everything else about him would seem to be the opposite of that concept. His look, style and demeanor are more in line with being a classic bro, the type of person who most people would expect to utterly shun being politically correct. This contrast is what makes him so intriguing.
Being the way he is naturally put PC Principal at odds with Eric Cartman, the least politically correct person who has ever existed. That wasn't a surprise to anyone who has watched South Park as Cartman delights in being horrifically offensive. What was impressive was that PC Principal was immune to Cartman's shenanigans and absolutely defeated him every time they butted heads. Then, Jimmy Valmer came along.
Of all the people to successfully oppose PC Prinicipal, no one expected it to be Jimmy. When PC Principal read an offensive word in the school paper, he threatened to break the legs of whoever wrote it. Using bullying and violence to promote his PC agenda was normal for him. But Jimmy was the person who wrote the article, and he wasn't exactly concerned about having his legs broken.
Their battle was chronicled throughout Season 19, Episode 8. When PC Prinicipal found that he couldn't force Jimmy to do what he wanted, he shut Jimmy's paper down. Jimmy responded by continuing the paper outside of the school and finding inventive ways to embarrass his new enemy. Jimmy essentially had PC Principal beat by highlighting the man's hypocrisy at every possible opportunity -- and there were more than a few.
Ultimately, PC Principal defeated Jimmy with the help of Nathan, Jimmy and Timmy's long-time rival. But that doesn't change the fact PC Principal didn't have an answer for Jimmy or any of the accusations he made against him. In the end, this encounter actually served to humanize the character, in part beginning the PC Principal's transition from being an antagonist at the beginning of Season 19 to being a protagonist by the end of it.