Jeff is an impressive orator known for being persuasive and passionate in the delivery of his arguments even if he doesn't really believe what he is saying is true. This skill is what made him such a formidable attorney and it's an ability which has served him well in his time at Greendale. Although he has sometimes used his way with words for manipulating others, often he will break out his patented Winger speeches to bring a meaningful resolution to a conflict involving the study group. On rare occasions, not every speech is given by Jeff and someone else in the study group or later in the Save Greendale Committee will end the episode with the lesson to be learned. The debut of these speeches was in the Season One episode "Pilot".
“We are the only species on Earth that observe "Shark Week". Sharks don't even observe "Shark Week" but we do. For the same reason I can pick this pencil, tell you its name is Steve and go like this (breaks pencil) and part of you dies just a little bit on the inside because people can connect with anything. We can sympathize with a pencil, we can forgive a shark, and we can give Ben Affleck an academy award for Screenwriting.”— Jeff
“People can find the good in just about anything but themselves. Look at me, it's clear to all of you that I am awesome but I could never admit that because that would make me an ass but what I can do is see what makes Annie awesome. She's driven, we need driven people or the lights go out and the ice cream melts. And Pierce, we need guys like Pierce, this guy has wisdom to offer...”— Jeff
“We should listen to him sometime, we wouldn't regret it.”— Jeff
“And Shirley, Shirley has earned our respect, not as a wife, not as a mother, but as a woman. And don't test her on that because that thing about the jukebox was way too specific to be improvised. And Troy, who cares if Troy thinks he's all that. Maybe he is, do you think astronauts go to the moon because they hate oxygen? No. They're trying to impress their high schools prom king. And Abed, Abed's a shaman. You ask him to pass the salt and he gives you a bowl of soup, because you know what? Soup is better, Abed is better, you are all better than you think you are, you are just designed not to believe it when you hear it from yourself. ”— Jeff
“ I want you to look at the person to your left... Sorry look at the person sitting next to you. I want you to extend to that person the same compassion that you extend for sharks, pencils, and Ben Affleck. I want you to say to that person I forgive you.”— Jeff
Inside Borchert Hall, Jeff delivers his closing arguments to a disciplinary tribunal formed to deal with Britta who had cheated on her Spanish test:
“Gentlemen, I'm sure you suspected that Ms. Perry was pretty odd before the recess but if you could have heard all the stuff she was telling me in the showers you would realize she is all the way out of her entire damn mind. She doesn't want to succeed because she doesn't think she can so she goes out of her way to fail. That's crazy! But, do we really want to make it a crime to be crazy at Greendale? I mean look at us. You two are arguing about status at a college that correspondent schools make fun of. Dean, you want so bad for this place to be Ivy League that you are putting us at risk of electrocution because everyone on this campus is nuts.”— Jeff
“And the reason I know that respect is a tool is because it clearly is not a natural thing and we forget to use it all the time and then we start to compete with each other and exploiting each other and humiliating each other and controlling each other and we lose each other and without each other we'll go extinct and that's a fact.”— Jeff
“We know he's dangerous, unpredictable, selfish, we know he uses his name to make bad puns.”— Jeff
“Guilty as Changed.”— Chang
“When he talks, he over and under emphasizes words seemingly at random. When he eats, he holds his fork like a murderer's knife, gnawing at it's skewered payload like a deranged woodland rodent.”— Jeff
“Bring it home!”— Chang
“We know he smells like Band-Aids, we know he dresses like a Cuban cab driver, we know he exhibits, nay, flaunts proudly obvious symptoms of over a half dozen disorders you wouldn't wish on your worst enemy's pets.”— Jeff
“Feel the heat!”— Chang
“We know these things about Ben Chang and so much more than we ever wanted to know about him. Why? Because it's there. It's on the surface. What you see may be what you don't want but it's also what you get. Who is this kettle corn popping phantom? This human question mark, this number 8 scoop of vanilla tapioca with a PhD in being swell and a Masters in "Everybody loves me"? Who is it?! We may never know. I only know one thing: Nobody is this good a person...and nobody can get any worse then this.”— Jeff
Later, Jeff then runs to someones doorstep and delivers this admission:
“Don't say anything until I've said what I've got to say. I've known you for almost two years now and I've never taken you as seriously as I should have. You are the strangest, coolest, most genuine person I've ever met and the thing that scares me about you is how good you make me wish I was. Help me Rich, help me become like you. I mean, I am so amazing but I'm not perfect...you are...give me that power...so I can abuse it.”— Jeff
In "Biology 101," Jeff tries to make a heartwarming excuse why Pierce doesn't need to be in the same class as them:
“I think we've evolved beyond reliance on a group at all. Aren't we just actual friends now no matter where we are. You know what's magic about this table? It magically keeps our books from falling on the floor. The table's for studying, but as friends we've evolved. And let us use that first breath of crisp, new, super-evolved air to declare proudly and in one voice: Pierce! We'll see ya when we'll see ya.''”— Jeff
Later in that same episode, Jeff takes back what he's said about the nonexistent reliance of the table:
Pierce isn't crazy. The table is magic. As someone who's been on the other side, I can tell you it is been a scary, lonely, Chang-filled world out there. And sure, this group has sprouted some legs, but why are we in such a rush to leave the tide-pool when the only things waiting for us on shore are the sands of time and the hungry seagulls of slowly growing apart.
Listen up, Colonel crypt-keeper, I could live a million years, and I could spend every minute of it doing important things, but at the end of it all I would only have lived half a life if I have not raised a son. This was a gift that was handed to you. You squandered it. And the reason you have so much hatred in your heart is because you are trying to fill a hole where your kid is supposed to go. And now, it's too late. Now, you're just stomping around trying to prove you exist. Well, mission accomplished. But here's a question I'd like to pass to you from every son of every crap dad that ever lived: "So what?" I'm done with you. He's done with you. The world is done with you.
“No, woman. We don't have to go to anybody. And the idea we do is a mental illness we contracted from breath mint commercials and Sandra Bullock. We can't keep going to each other until we learn to go to ourselves. Stop making our hatred for ourselves someone else's job and just stop hating ourselves.”— Jeff
"Introduction to Finality" Jeff is representing Shirley in Greendale Court over a dispute between her and Pierce regarding their new sandwich shop and is told by Alan to throw the case in order to get his old law firm job back:
“I have no closing statement because I'm throwing the case. No, no, it's okay. It's fine...don't worry. My client, Shirley Bennett, my friend of three years- she told me it was okay. She said what I want is more important. She's right...right? I mean, guys like me will tell you there's no right or wrong, there's no real truths...and as long as we all believe that, guys like me can never lose. Because the truth is, I'm lying when I say there is no truth. The truth is- the pathetically, stupidly, inconveniently obvious truth is- helping only ourselves is bad and helping each other is good. Now, I just wanted to get out of here, pass Biology and be a lawyer again instead of helping Shirley-that was bad. And my former colleague wanted so badly to keep his rich client happy that he just asked me to roll over in exchange for my old job. So, I guess we all walked in here pretty bad. But now Shirley's gone good. Shirley's helping me. It's that easy: you just stop thinking about what's good for you and start thinking about what's good for someone else...and you can change the whole game with one move. Now if you like this idea, you can make it true by doing something good for everyone here: throw this case out of court. It's dumb. That is all.”— Jeff
“I'm sorry. You should take some credit for whom I've become. So, let me tell you how I turned out just so you're crystal clear on your impact. I am not well-adjusted. More often than not, I am barely keeping it together. I'm constantly texting, and there's no one on the other end. I'm just a grown man who can't even look his own friends in the eye for too long because I'm afraid that they'll see that I'm broken. So, you get credit for that. One time, when I was in 7th grade, I told everybody at school I had appendicitis. I wanted somebody to worry about me, but when Beth Brennan asked to see the scar I didn't wanna get found out. So, I took mom's scissors, and I made one. It hurt like hell. But it was worth it because I got 17 cards, and I still keep them in a box underneath my bed 22 years later because it proves that someone at some point cared about me. Want to see the scar? So, I give you credit for that, too. This is me.”— Jeff
We need to make reparations. We have to start giving back because Greendale has given us so much. It gave us the study room, and that study room is our home. But our home is more than those four walls, and our family is more than the seven of us. It’s all of Greendale. And everyone deserves to have what we have.
Jeff talks to Troy after realizing the reason behind his "body switch" with Abed in "Basic Human Anatomy":
I wish I had the courage to commit to a bit like you "Abed" or to a relationship like Troy. Committing is hard cause we are all scared of what happens when we find out we committed to the wrong thing...but there's no shame in what Troy's done. He put himself out there and he really tried and that proves he cares. That said, and as hard as it may seem right now, Troy needs to show he cares. He needs to put himself out there and own how he feels. That proves he's a man.
Three and a half years ago, when I came to Greendale, I met six very important people. … Sorry, seven. And meeting these people changed my life. Yeah. I’m sorry. I – I don’t know what to say. [study group laughs and objects] I’m so used to being the guy who can talk his way out of anything, but… what do you say when you don’t want a way out? What you all have done for me is indescribable. It’s unbelievable. And my love for you is immeasurable, even when you split it seven ways.
“I have discovered the meaning of the giant hand. A hand has two functions; to grip and to release. But without both of these powers it is useless. Like newborn infants we grab what comes near us. Hoping to control it, taste it, jam it into another child's eye. But the time we spend in control of our world is the time we spend letting go of others. Ideas, stories, pride, girls in soft sweaters, video games, buttered noodles... Grip one for too long and you lose so much that you've never held. This giant hand was sent to all of us as an invitation to increase our mastery over the power to hold on...and let go.”