Jeff Winger, the product of a divergent timeline in which the study group suffered great personal losses. Jeff himself lost his right arm while trying to put out a fire. Devastated by those tragedies, the Abed of that reality dubbed this The Darkest Timeline, and suggested they become as dark and twisted as the reality they had to endure. Although Jeff at first refused, he had a change of heart and after freeing Evil Annie from the Greendale Insane Asylum, he now plots with the rest of the "Evil study group" to destroy the "Prime Timeline". His first appearance was in the Season Three episode "Remedial Chaos Theory". He is portrayed by Joel McHale.
|In the study group's third year at Greendale, Troy and Abed decided to move in to an apartment together. A housewarming party was thrown where a the roll of a Yahtzee die determined who would go downstairs to grab the pizza from the delivery guy. Six different scenarios unfolded that split off from the "Prime Timeline" one which ended up becoming The Darkest Timeline. In that alternate reality, a chain of events led to Jeff having his arm amputated after it was severely damaged when he tried to put out a fire. The Abed of that timeline suggested an outrageous plan; they would all commit to becoming "evil" by wearing felt goatees, cross over to the "Prime Timeline" and take over their counterparts' lives. Jeff, having sunk into a bitter depression due to his loss, angrily refused Abed's suggestion declaring his hatred of him before storming out of the study room ("Remedial Chaos Theory").
|However, it's later shown he changed his mind and had come to embrace his dark side. After Evil Annie's criminal misdeeds landed her in the Greendale Insane Asylum, Jeff, acting as her defense attorney, went to court to fight for her freedom. Playing on the sympathy of the court due to his missing arm and arguing Annie was too beautiful a person to lock away, he succeeded in securing her release. After she was freed, the two embraced and she asked him if he had a problem with the age difference now. He replied he wished she was younger and then revealed he and the remaining study group were plotting to destroy the "Prime Timeline". The two laughed maniacally before kissing each other passionately ("Intro to Knots").
|Eventually, Evil Jeff travels to the Prime Timeline to corrupt it like Evil Abed had intended before he had a change of heart. He arrives along with Evil Annie on the day of Jeff's graduation. Upon learning he was offered a job at his ex-partner Mark's new law firm, they decide to force him to accept the job. To that end, they plan on turning the Study Group against him. Starting with Annie, Evil Jeff impersonates Jeff and visits each of his friends and insults them causing them to refuse to show up to his graduation ceremony. The only one not fooled by him is Abed who immediately identifies him as "Evil Jeff". Using a advanced paintball weapon, he shoots Abed, which transports him to the Darkest Timeline.
Meanwhile at the graduation ceremony, Jeff finds that no one has shown up to the party except Evil Annie. She pretends to be Annie and flirts with him while at the same time trying to get him to accept Mark's job offer. Evil Annie calls in Evil Jeff when she fails in her seduction. Evil Jeff again tries to persuade Jeff to join the new law firm and return to his former life as a sleazy lawyer. When Jeff refuses, Evil Jeff attempts to shoot him with the same reality-warping paintball weapon he used against Abed. Instead, he shoots Ben Chang, who stumbled on the scene and valiantly sacrificed himself by intercepting the bullet. This allows Jeff time to escape, angering his duplicate and Evil Annie. At that moment, the rest of the Evil Study Group appears, having crossed dimensions to provide assistance to the pair.
After suiting up in matching Darkest Timeline leather apparel, Evil Jeff leads his Evil Study Group on a hunt to find each of their doubles on campus. Equipped with more paintball weaponry, he now intends to send all of the "Prime Timeline" study group to the Darkest Timeline. They arrive in the cafeteria only to be surprised by the arrival of Evil Pierce. It turns out he faked his own death to teach them a lesson. After learning they all went to the "Prime Timeline" he followed them there to offer his help. However, he misunderstood what Evil Jeff told him about the mission and shot himself with a paintball gun and sent himself back to the Darkest Timeline. Evil Britta shot herself accidentally as well, causing Evil Jeff to be exasperated at his cohort's stupidity. It's then that the "Prime Timeline" study group reveals they are inside the student lounge when Britta loudly takes exception to Evil Jeff berating her counterpart.
The two groups face off as Annie, Shirley, and Troy quickly dispatch their darker alternate selves. Only Evil Jeff is left, who in the ensuing chaos of the fight loses track of his duplicate. It turns out his "Prime Timeline" double was hiding behind a couch in the student lounge. Jeff is encouraged by Abed, who makes him aware that this entire scenario is simply a fantasy generated by his own anxiety about graduating and leaving Greendale behind. Jeff then calls out to Evil Jeff who shoots a single paintball pellet his way. Jeff stands there unmoving as the paintball pellet races towards him and freezes it in place. Evil Jeff is puzzled at this turn of events as his counterpart shoots him with his own paintball gun sending him back to the Darkest Timeline.
Afterwards, another peek into the "Darkest Timeline" shows that Evil Jeff and his Study Group have settled back into their lives in that reality. Evil Jeff is shown interrupting Evil Troy and Formerly Evil Abed's morning show. Still wearing his leather outfit, he expresses his annoyance that they are still doing the show. He points out the fact that it's fake and there isn't even an audience. They reply they are aware it's not real and tell him they will meet him later for lunch. Evil Jeff tells them he'll see them there and after he leaves Evil Troy and formerly Evil Abed do their signature catchphrase to close out the talk show ("Advanced Introduction to Finality").