List of Community characters
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Jeffrey Tobias "Jeff" Winger (played by Joel McHale), is a sardonic, quick-witted ex-lawyer attending Greendale Community College. He was born in Denver, Colorado to his parents William Winger and Doreen Winger née Fitzgerald. His father divorced his mother when he was very young and later had another child named Willy Jr., Jeff's half-brother. When he was 10, he was bullied and humiliated in front of his friends at a YMCA over a game of foosball, eventually wetting his pants. Unbeknownst to either of them at the time, the girl who beat him was his study-group peer Shirley, who was then 12 and a bully. He tells her that he had to change schools, as well as his hair, his clothes, even his personality because of the incident. In 1997, around age 19, Jeff submitted an audition tape for MTV's ''The Real World: Seattle'', which would later come back to haunt him during an election for Greendale's student-body president. In the Season 5 episode "Geothermal Escapism," as study-group member Troy is about to leave Greendale, Jeff discretely reveals to him that he has "never set one foot outside Colorado."
Jeff was once a highly successful defense attorney with Hamish, Hamish, and Hamlin founded by Ted. At work, he was often partnered with another lawyer named Mark, and the two were known as "Tango & Cash," respectively. For over six years, he specialized in juvenile and traffic offenses, as well as DUI/DWA/DUID cases. During this period, in 2002, he successfully defended Ian Duncan from a DUI by comparing his accuser to 9/11, and they developed a friendship. After a successful case in which he defended a stripper named Mysti, the Colorado Bar Association began scrutinizing his background. His rival and friend Alan Connor then betrayed him by sending the CBA an incriminating email, revealing that Jeff did not receive a bachelor's degree from Columbia University but got one that was "less than legitimate" and "better than real" from the country of Colombia. He strikes a deal with the bar to prevent him from being disbarred, on the condition that he graduated from an existing college with an actual degree. While brainstorming the right college to attend, he ate at a frozen-yogurt restaurant and overheard a conversation elucidating the ease of graduation from Greendale Community College. Remembering that Ian Duncan was a professor there, Jeff decided to attend, hoping that Duncan would help him graduate as quickly as possible.
In the pilot, Jeff forms and joins the study group because he is attracted to his classmate Britta, whom he tries (and fails) to seduce. However, by the end of the pilot episode, he is kicked out of the group before being asked to join back in. After Britta definitively rejects his advances, Jeff begins flirting with his statistics professor, Michelle Slater, and eventually starts dating. Before this, he shares several UST-y moments with another study group member, Annie, after she kisses him to win a championship debate. After Professor Slater breaks up with him, he sleeps with Britta in the study room after a paintball fight in "Modern Warfare." At the end of season one, Britta and a newly interested Professor Slater compete for his affections, culminating in Britta professing her love for him at the school's "Transfer Dance" in "Pascal's Triangle Revisited." Soon after, he meets Annie outside, and they kiss. At the beginning of season two, Britta recants her declaration of love for Jeff, saying she was caught up in the spirit of competition. He comes to an uneasy understanding with both Britta and Annie. Later in the season, the study group finds out that Britta and Jeff had been hooking up in secret throughout the year, and both of them then realize they have no interest in continuing to hook up. Jeff and Annie both wrestle with their romantic impulses towards each other for much of Season 3.
Jeff is continually sarcastic, suffers occasional bouts of rational-agent sociopathy, and often displays much less enthusiasm for Greendale activities than other members in his Spanish study group. Initially, Jeff tends to be manipulative and dismissive towards his study group, but gradually shows increasing respect and appreciation for the other group members and treats them as friends. Jeff enjoys being in positions of authority and command and acts as the effective leader of the group. It becomes apparent that several members of the group rely on him playing this patriarchal role, though Pierce Hawthorne, as an elder male and the most sociopathic member of the group, naturally resists and tends to insult Jeff whenever he can, despite Pierce's lack of wit. Yet in the episode "Spanish 101," Jeff develops a detente with Pierce. The other members have also bristled at how Jeff is the "obvious" person to be their group leader but regularly mocks or disregards such responsibilities, leading to times when they have been receptive to leadership from other members (particularly Troy). By the end of Season 3, Jeff has reconciled his roles as a suspended lawyer and head of the study group: he ignores his sleazy former law colleague's promise/threat to either get Jeff back into the firm or ruin his career based on whether he throws Shirley's sandwich-shop case, wins the proceeding for her, and accepts Shirley and Pierce's joint offer to have him serve as managing counsel for their new collective shop venture.
Because of his background experience as a lawyer and his confidence, many people, including Dean Pelton and Señor Chang, seek help from Jeff. Jeff's adventures include stints as a member of the debate team and substitute glee club, and editor of the school newspaper, as well as efforts to improve Chang's professional and love lives. Due to his competitive nature and air of superiority, Jeff has a problematic relationship with his accounting, billiards, and pottery professors, and he ends up doing poorly in their classes. One of his remarkable traits is his perfectly unkempt hair and the mystery of how he maintains its bed-headed perfection, which Dean Pelton describes as "crispy" to the touch.
As the show progresses, Jeff starts dealing with his anxious and hateful feelings towards his father, who abandoned him. "Intermediate Documentary Filmmaking" presents his issues with the latter. By the end of the episode, Jeff had realized that he has many things to say to his father, many of which came out towards Pierce when Jeff attacked him in a fit of rage. Also, in one of the timelines of "Remedial Chaos Theory," Pierce brings up the subject of Jeff's father, which Jeff immediately evades. Also, while attempting to come up with a toast for Shirley's wedding, Jeff drunkenly reveals that his jaded views on marriage result from the failure of his parents' marriage and his father subsequently leaving them. The season 3 finale, "Introduction to Finality," shows Jeff finally attempting to contact his father. He also admits that he thinks of himself as "broken."
In the Season 4 episode "Cooperative Escapism in Familial Relations," Jeff finally meets his father, William Winger Sr., as well as a half-brother, William Jr. Jeff eventually reveals that after his father left, he told his classmates in seventh grade that he had to get an appendectomy, to have someone "worry about [him]." When one of them asked to see the scar, Jeff intentionally gave himself a scar with his mother's scissors on his abdomen to keep up the charade. He still possesses all of the get-well cards he received from his classmates in a box under his bed because "it proves that someone, at some point, cared about me." It is implied that by meeting his father in person and telling him how much he was hurt, Jeff has faced and began to deal with many of his insecurities stemming from the abandonment. It is also shown at the end of the episode that he and his half-brother are on good terms.
In the season four finale, "Advanced Introduction to Finality," Jeff receives a Bachelor of Education degree and finally graduates from Greendale.
In the fifth season, after Jeff graduates, his law firm has failed. He is approached by Alan, who convinces him to sue Greendale. He returns and eventually turns back on the lawsuit when he finds out how much the school means to people. He becomes a law teacher at the school and forms the Save Greendale Committee. He has trouble getting used to being a teacher at the school and struggles with a drinking problem. On his 40th birthday, he has a midlife crisis and overdoses on alcohol and Korean fertility pills, fantasizing an episode of ''G.I. Joe'' featuring the study group while unconscious ("G.I. Jeff"). When the school is sold to Subway, Jeff and Britta get engaged, but once they save Greendale, the engagement is broken.
In season six, Jeff continues to be a subpar teacher with alcohol problems (including drinking in the classroom) and has an existential crisis when he realizes that he is the member of the group with the least direction in life, and will likely be the last of them ever to leave Greendale.