Jackie Chiles is a well dressed, fast-talking lawyer who describes things with a series of adjectives, “It’s lewd, lascivious, salacious, outrageous!”
A parody character of O.J. SImpson’s defense attorney, Johnnie Cochran, he represents Kramer in a series of lawsuit against Sue Ellen Mischke, Java World, and even big tobacco.
He also represents Jerry, George, Elaine, and Kramer when they are arrested for violating the good samaritan law in the Finale.
According to the diplomas in his office, Chiles attended Dartmouth College and Stanford Law School. Jackie Chiles is played by Phil Morris.
Carrying over a storyline from a previous episode, The Postponement, Kramer seeks restitution for burning himself on a caffe latte that he claimed was too hot. So Kramer gets a fast-talking litigator, Jackie Chiles, to help him sue Java World. Kramer and Jackie head over to Java World’s HQ and learn that they would like settle.
They offer Kramer a lifetime supply of coffee, but before they mention money, Kramer, already pleased with a lifetime of free cafe latte’s accepts the deal without any money.
Later in the cab Jackie argues with Kramer over his decision, “twenty years practicing law, I’ve never experienced anything like this.”
While taking George’s car to a car wash, Kramer and Jerry get into an accident when both are staring at Sue Ellen Mischke who was wearing a bra as a top.
Elaine convinces Kramer to take Sue Ellen to court for damages to the car and they get Jackie Chiles to represent them. At the trial, Jerry reluctantly admits that Sue Ellen was the cause of the accident, but as the trial is about to end, Stan the caddy tells Kramer to get Sue Ellen to try on the bra.
Chiles argues against the idea, but Kramer insists that the judge have her try on the bra to see if it fits. When it doesn’t fit, it costs Kramer and Elaine the trial and upsets Jackie, who claims “a bra’s gotta fit right up a person’s skin, like a glove!”
The Friars Club
When Kramer tries polyphasic sleep, or the Da Vinci sleep cycle, he falls asleep on his girlfriend Connie while making-out.
Thinking that he’s dead, Connie calls her mobster friends to get rid of him, and they dump Kramer into the Hudson River in a sack. Later, Kramer shows up at Connie’s door with the police and points her out to the officers, who place her under arrest.
She asks to cops if she can call her lawyer and when he answers his phone it happens to be Jackie Chiles. Jackie asks who she was accused of attempting to murder and upon learning that Kramer is that the person, he tells Connie, “I don’t want nothing to do with it.” and hangs up.
When Kramer is kicked out of the coffee shop for smoking a cigar, he decides to open up his apartment as a smoking lounge.
But after experiencing a lifetime of smoking in 72 hours, Kramer’s face becomes leathery, like an old catcher’s mitt.
So he decides to take action, on account that his face is his livelihood, and visits Jackie Chiles to discuss a case against the tobacco company for ruining his good looks.
After some convincing, Jackie agrees to represent Kramer but again gets burned when he agrees to a settlement without Jackie’s input. The settlements ends up being that Kramer gets a billboard with his face on it in Times Square, causing Jackie to admit “this is the most public yet of my many humiliations.”
While waiting for a plane to be repaired in Latham, MA, Jerry, George, Kramer, and Elaine witness an overweight man getting carjacked at gunpoint. Instead of helping him, they make jokes about his weight while Kramer films it and then they just walk away.
The victim reports them to an officer on scene who arrests them for not helping out. Jerry and his friends do not have any choice but to call on Jackie Chiles to represent them for the upcoming trial.
Jackie: Yeah, see they like to sell their own coffee.
Kramer: Yeah, now is that going to be a problem?
Jackie: Yeah that’s going to be a problem. It’s gonna be a problem for them. This a clear violation of your rights as a consumer. It’s an infringement on your constitutional rights. It’s outrageous, egregious, preposterous.
Kramer: It’s definitely preposterous.
Kramer: So ah, what do you think Mr. Chiles.
Kramer: Jackie. I mean, we have a chance?
Jackie: Do we have a chance? You get me one coffee drinker on that jury, your gonna walk outta there a rich man.
Jackie: You put the balm on? Who told you to put the balm on? I didn’t tell you to put the balm on. Why’d you put the balm on? You haven’t even been to see the doctor. If your gonna put a balm on, let a doctor put a balm on.
Kramer: I guess I screwed up huh Jackie?
Jackie: You’re damn right you screwed up. Where the hell did you get that damn balm anyway?
Kramer: The Maestro.
Jackie: The who? What are you talking about Maestro?
Kramer: My friend he’s a conductor.
Jackie: Oh oh oh, so a Maestro tells you to put a balm on and you do it?
Kramer: Well my stomach was burning.
Jackie: I tell you what this is. This is a public humiliation.
Jackie: I’ll take it? Who told you to take it? Did I tell you to take it?
Jackie: I know the Maestro didn’t tell you to take it, he wasn’t there.
Kramer: Well I thought we were lucky to get anything.
Jackie: Free coffee?
Jackie: I don’t want free coffee. It’s not hard to get coffee. I can get my own
damn coffee. I wanted to hear what came after that “Plus”.
Kramer: Well I didn’t hear any Plus.
Jackie: 20 years practicing law I’ve never experienced anything like this.
Kramer: The we saw this woman, and she was wearing a bra with no top.
Jackie: No top? She didn’t have a top on?
Kramer: No. So I got distracted and I crashed the car.
Jackie: Well how would you describe this woman? Would you say she was an attractive woman?
Kramer: Oh, yeah.
Jackie: So we got an attractive woman, wearing a bra, no top, walkin’ around in broad daylight. She’s flouting society’s conventions!
Kramer: She was flouting.
Jackie: That’s totally inappropriate. It’s lewd, vesuvius, salacious, outrageous!
Kramer: It was outrageous. And she’s the heir to the O’Henry candy bar fortune.
Jackie: Could you repeat that?
Kramer: I said she’s the heir to the O’Henry candy bar fortune.
Jackie: O’Henry? That’s one of our top-selling candy bars. It’s got chocolate, peanuts, nougat, it’s delicious, scrumptious, outstanding!
Jackie: What was your golf score, the last round you played…before you shoulder was injured?
Kramer: Three under par.
Jackie: Oooohhhh, three under par…That’s what the professionals shoot, isn’t it?
Kramer: If they’re lucky.
Jackie: Damn fools! Look at that! We got nothin’ now, nothin’! I’ve been practicing law for 25 years, you’re listenin’ to a caddy! This is a public humiliation! You can’t let the defendant have control of the key piece of evidence. Plus, she’s trying it on over a leotard, of course a bra’s not gonna fit on over a leotard. A bra gotta fit right up a person’s skin, like a glove!
Jackie: Attempted murder? Of whom?
Connie: This guy, Kramer.
Jackie: Oh. (hesitantly) Cosmo Kramer?
Connie: Yeah, that’s right.
Jackie: I don’t want nothing to do with it.
Jackie: My vacation was restful, splendid, magnificent. In fact, next time I’m plannin’ on going to Kofu.
Kramer: Jackie we gotta talk.
Jackie: No way, Kramer. You’ve brought nothing but a mountain of misfortune and humiliation. Now get out.
Kramer: But Jackie–
Jackie: I said out.
Kramer: Jackie, I think I gotta case against the tobacco companies.
Jackie: The who?
Kramer: The tobacco companies.
Jackie: I’ve been wanting a piece of them for years.
Jackie: Did that cigarette warning label mention anything about damage to your appearance?
Kramer: No, it didn’t say anything.
Jackie: So you’re a victim. Now your face is shallow, unattractive, disgusting.
Kramer: So Jackie, do you think we gotta case?
Jackie: Your face is my case.
Jackie: Miss Wilkie, your tobacco company has turned this beautiful specimen, into a horrible twisted freak.
Kramer: Who could love me?
Ms. Wilkie: I disagree. In fact, I feel Mr. Kramer projects a rugged masculinity.
Jackie: Rugged? The man’s a goblin. He’s only been exposed to smoke for four days. By the time this case gets to trial, he’ll be nothing more than a shrunken head.
Ms. Wilkie: All right, Mr. Chiles. You’ll have our offer by tomorrow. Good day, gentlemen. (She exits)
Kramer: Bye-bye. Jackie, you did it. We’re rich.
Jackie: You better believe it. Jackie’s cashin’ in on your wretched disfigurement.
Kramer: Mrs. Wilkie, from the tobacco company called me. We had a little pow-wow.
Jackie Chiles: A pow-wow? Who told you to have a pow-wow? I didn’t tell you to have pow-wow.
Jackie: This is the most public yet of my many humiliations.
Sidra: Come on, Jackie. Let’s go.
Chiles: Oh, and by the way, they’re real, and they’re spectacular.