In "Debate 109," Simmons is first mentioned by Dean Pelton, who refers to him as City College's star debater. Pelton believes that as a former lawyer, Jeff is the only one who could be a match for Jeremy. He is later seen onscreen for the first time at the debate championship being held in Greendale's gymnasium. After Annie delivers her opening argument, Simmons is then introduced to the roars of his fellow City College students who are in the audience to support him. In his opening argument on the goodness of man he brings up not only the rise of kidney donations but also the fact that Dean Pelton held the door open for him because he was in a wheelchair. When he finishes his statement the City College students continue to cheer their encouragement. Jeff then offers up his own opening argument and charms the crowd into singing along with the ELO song "Evil Woman".
Simmons looks worried at how easily the crowd is swayed but his fears end up being unfounded when Jeff scores zero points for his efforts. The rest of the debate is postponed until tomorrow due to the Greendale basketball team having reserved that time in the gymnasium for practice. Outside the gym, Jeremy and his debate partner 'Ropati find Jeff and Annie and start to taunt them. Jeremy mocks Jeff earlier arguments by telling him in singsong that he expected more from a former attorney. Annie sticks up for her partner but gets joked herself by Jeremy for having gotten only 8 points for her arguments. When Jeff steps in to defend her, Jeremy launches into another song mocking Annie's past Adderall addiction and her life as an outcast in high school. An angry Jeff then gets in Simmons face and tells him that was the last straw and they will "debate the living crap" out of him tomorrow. Jeremy is greatly amused at this seemingly looking forward to the challenge.
The next day, Jeremy finishes up a stirring argument on the goodness of man by quoting a poem by Franz Wickermeyer: “Snow falls from the heavens pure. We can not blame the snow for being soiled by the Earth". The audience (particularly Troy who is there along with the rest of the study group) and judges are all moved by his statement. When it's Jeff's turn to rebut, Simmons taunts him by asking him what he's going to sing now adding that he is in the mood for some Sade. Instead , Jeff offers up his own quote: "There is none righteous, not one". This trumps Jeremy's quote when Jeff reveals that it's source was from Jesus. Jeremy looks at Annie who silently lets him know that it's on now. A fierce competition ensues with both teams struggling for dominance. After a few rounds, it's clear that City College is trailing in points and losing the debate. Jeremy decides to go off book and rips up his note card and resolves to make a bold statement in order to make a comeback.
On the dais, he makes his wheelchair run at full speed towards Jeff. He then makes the chair come to a sudden stop which sends him flying through the air towards the Greendale debate team. Instinctively Jeff catches him and Jeremy then states to the judges that although his opponent hates him but caught him anyway proving that man is good. The judges are impressed by his unorthodox argument as the City College crowd cheers their approval. Annie, however, comes up with a quick rebuttal and pulls Jeff in for a kiss which makes him immediately drop Simmons who does a face plant onto the floor. Breaking the kiss, Annie then declares that Jeff was horny and he dropped Simmons proving that man is evil. The audience and judges are stunned by the argument. The silence is broken when one of the debate judges declares that Greendale won. As the Greendale students in attendance cheers their debate teams victory, Jeremy struggles to deal with his defeat and maintain his composure while stuck in an undignified position.