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|Jeffery Tobias Winger|
Jeff Wingeris a snarky, glib lawyer attending Greendale Community College. He was a lawyer until the Colorado Bar Association found out that he did not get a bachelor's degree from Columbia University but, in fact, got one that was "less than legitimate" and "better than real" from the country of Colombia. Jeff returns to college by attending Greendale Community College as a "deal" with the bar in order to prevent him from being disbarred. He consequently hopes to graduate as quickly as possible.
Initially, Jeff forms and joins the study group because he is attracted to fellow student Britta who he hits on, despite her rejection of his advances. While this dynamic slips into friendship, they eventually sleep together, despite denying any feelings they may have for each other to the rest of the study group. He also dates his statistics teacher, Professor Slater and, at of the end of the first season, kisses Annie, despite her being much younger than him. Nevertheless, by the beginning of the second season, it becomes clear that he doesn't want to pursue anything further with any of them.
Jeff is continually sarcastic and often displays much less enthusiasm for Greendale activities than other members in his Spanish study group. Because of his background as a lawyer and his compelling personality, many people, including Dean Pelton and Señor Chang, seek help from him. These ventures include stints as a member of the debate team and editor of the school paper and efforts to improve Chang's professional and love lives. Due to his competitive nature, he has difficult relationships with his accounting, billiards, and pottery teachers when he does poorly in their classes. He enjoys being in positions of authority and acts as the effective leader of the group. It becomes apparent that several members of the group rely on him playing this role while Pierce tends to insult him whenever he can, despite his lack of wit.