Thoughts I’ve been having about the relationship between Jeff and Pierce:
As you get older, theoretically you should become a better and better human being. You learn from each mistake, you don’t make those mistakes again, you become a smarter and wiser and nobler person, etc. The problem with this is that pretty much everybody fails to learn some things in their lives. And some people, for all of their experience, seem to fail to learn anything. Or they learn the wrong lessons. Pierce is the former, Jeff the latter. For all of their supposed accumulated knowledge, they know relatively little about doing the right thing. They start off selfish and vain and often petty.
Jeff looks down on Pierce at first, but in a detached kind of way. He sees that Pierce is bigoted and short-sighted and foolish, but simply can’t be made to care. As he grows closer to the other members of the study group over the course of the year, however, and sees them grow and learn and become better people, he finally starts learning the right lessons. He’s not suddenly a changed man of course—his flaws are still apparent. But he has learned to care more about these other people.
Pierce, on the other hand, doesn’t really. He seems to grow at times, but these are false epiphanies, the kind often had by people who habitually do not learn from their wrongs and mistakes. He seems to learn his lesson, but forgets it soon afterward. His stubbornness in this way is stereotypical of people of his age—if people don’t retain wisdom through their younger years, they seem to often become less and less willing to hearing it in their advanced age. Pierce is set in his ways. He hasn’t grown in the last twelve years he’s spent at Greendale, and he doesn’t seem like he ever will. In season 2, Jeff finally starts to care about this. He especially resents the way Pierce tries to be a father figure to him because he doesn’t want to admit that the two of them were cut from the same cloth. His inner selfish jerk doesn’t want to believe it because he still retains that need to be superior to everyone, and his growing compassionate side doesn’t want to admit that he was ever so resistent to learning as Pierce. So he grows more and more hostile with Pierce, and when Pierce leaves at the end of the season finale, he feels the best about it. I might even go so far as to say that Jeff has projected his problems onto Pierce, and thinks subconsciously that with Pierce gone, he can really become a better person.
(Pierce meanwhile does have some idea of his problem, acquired from years of rejection, but he’s too lazy, too afraid to risk anything, to try and learn anymore. He wants to take Jeff under his wing because he needs to convince himself that he is worth of being a mentor figure even though he isn’t.)
On a meta level, Pierce has never quite fit in with the others, probably due to Chevy Chase himself being notoriously difficult to work with. The smartest decision Dan Harmon and the writers made in season 2 was to exploit that, and make Pierce as much/more of an outside as Chevy seemed to be, and make that the season’s most important recurring development.* All of this is also why Pierce’s “booyah good person” moment in the season 3 finale is such a great Finale moment: it’s a ray of hope for him. It’s not a complete change, but it’s a learned lesson, and that’s a damn good start.
Anyway, now to figure out how to turn these thoughts into a fanfic…
* This also ties into a rant for another time about the important of the relationship between Jeff and Annie, and in turn the change in Britta’s character through the seasons.