Jeff Winger is a jerk. He’s selfish, egotistical, and doesn’t believe in doing things.
But everyone loves him anyway.
Guarascio and Port have revealed that in season 4 Jeff is going to meet his real father finally and along with the premier last Thursday, with the “new” Jeff, it appears that Jeffrey Winger isn’t just anxious to graduate and leave Greendale; Jeff Winger is, indeed, a human being with feelings.
Underneath Jeff’s snobby, fashion-concerned lawyer persona, past the hardcore, bad boy act, and beneath the flaunted sexual prowess – Jeff isn’t such a bad guy. In fact, if it weren’t for this guy, the Study Group wouldn’t exist; Community wouldn’t exist! So, at the end of the day, we at least owe him that thanks.
Jeff bonds (in his own way, of course) individually and intimately with each character. He forms close ties with the rest of the Study Group, and even with Chang and the Dean, whether he realizes it or not. When he was determined to win everyone a spot in History of Ice Cream, it wasn’t just because he wants to graduate. Without the Study Group, he has very little meaning. No quipping with Britta, no being mothered by Shirley, no parenting Troy, Abed, nor Annie (though maybe less parenting with Annie and more subconscious flirting), and no fearing Pierce – because ultimately, Jeff sees Pierce a possibility for his future self.
Each of the characters grounds Jeff in a different way, including Chang and the Dean. Even though Jeff adamantly doesn’t believe in doing things, both Crazy Chang and the Dean propel Jeff into fighting for the things he does believe in: the Study Group. Jeff is highly protective, particularly of Abed, and when Chang (like when he became a dictator and took over Greendale) and the Dean (like with his Hunger Deans) not only stand between Jeff and his goal but also in some form attack the Study Group (because the entire group suffers even if it’s just one character specifically targeted), Jeff does put aside his goal long enough to defend his turf.
Though, he always comes back to himself. Despite blaming it on his overly doting mother and never existent father, Jeff is just shielding his inner, still immature child-self. Which naturally he denies doesn’t exist.
So, as long as anyone is (or possibly is) looking, Jeff is a jerk, and probably when he’s really looking, too. But there’s no escaping that his jerk-ness is more a tool to help him achieve his goals (and ignore others), an act.