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. The debut of these speeches was in the Season One episode "Pilot".
"Anthropology 101" Jeff explains to the Anthropology class his theory on the class' first assignment; which tool of the nine given was the most important:
- “The tool most important to humanity's survival wasn't any of the nine in the box.”— Jeff
- “Go on.”— Professor June Bauer
- “The most important tool is respect.”— Jeff
- “Heh! GAY-U-H!”— Ben Chang
- “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
- “Heh! Gay fact! ”— Chang
- “That's my answer professor.”— Jeff
Latr, 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."
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."
- Britta: "I have to go to him."
- Jeff: "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 Sandara 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."
"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 Winger finally talks about finally seeing Greendale in a better light in episode Alternative History of the German Invasion:
|“||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.||”|
"Advanced Introduction to Finality" Jeff delivers a heartfelt speech at his graduation ceremony:
|“||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.||”|