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Sep 1, 2011 
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There's a scene I love in Tombstone, an otherwise inconsistent movie. It's the infamous gunfight at the O.K. Corral. The Earp boys, backed by Doc Holiday, head to the O.K. Corral to enforce Tombstone's new weapons ban on the Clanton boys and their gang. They catch the Clantons unawares. For a moment, it looks as if the Earps, by walking tall and projecting confidence and authority, are going to be able to make the Clantons give up their guns and end the confrontation without violence.
Then Doc Holiday — played with a fey combination of indifference, amusement, and sociopathy by Val Kilmer — delivers a slow, saucy wink to Billy Clanton, played by Thomas Hayden Church. Billy's expression goes from surprise to incredulity to outrage:
Wyatt sees what's happening and says "Oh, shit," but it's too late — the enraged Billy pulls his gun, and then everybody's shooting at everyone else.
I love that scene because it so perfectly captures what representing clients can be like. Litigation is ridiculously expensive, hopelessly unpredictable, and does a piss-poor job at vindicating values like "justice" or "fairness" or "truth." Quite often, settlement is the rational business decision, the rational outcome from a financial perspective. Under our flawed system, that's true whether the client's cause is righteous or bogus. You can demand your day in court, but it's a huge risk if you're a plaintiff and both a risk and an almost certainly unrecoverable massive expense if you're a defendant.
So: clients often decide that it's rational to try to settle, whether in front of a mediator or through attorney negotiation. But even though clients can be rational, they always retain the lizard brain, the part that wants their day in court where they can talk about how the other side is made up of mendacious assholes, and how righteous/bogus the lawsuit is. The urge to lash out at the people who wronged them/maliciously sued them is powerful. In short, even in the midst of a settlement negotiation that is proceeding very well and likely to produce what under the circumstances will be a favorable result, they want to give the other side Doc Holiday's saucy wink.
Unfortunately, the other side is made up of people with lizard brains, too. The clients on the other side (and, for that matter, even the lawyers) may react to your client's saucy wink with Billy Clanton's irrational, suicidal outrage, and then the whole settlement goes to hell, and everyone stubbornly plods to a ruinously expensive trial in front of people who couldn't get out of jury duty. The saucy wink may come in the form of provocative language at a mediation session, or it may come in the form of a client insisting on putting gratuitous swipes into settlement communications.
The client has a perfect right to reject settlement and go to trial. I see my role as advising the client about that, not telling the client what to do. But this is a context in which I argue more forcefully with a client than I would otherwise. It's simply foolish to waste time and money on mediation or negotiation just to tank it by preying — wittingly or unwittingly — on the human foibles of the other side. I get that this mediation or negotiation may wind up being the closest thing the client has to a "day in court" where he gets to express his outrage at the situation. But it's a situation where self-indulgent venting is harmful, unless the point is to end negotiation. That's why try to insist on a shuttle diplomacy approach in mediation so that the client can vent to the mediator, not to the other side, and not be exposed to the other side's venting. That's also why I ask clients to write out everything they want to say in a settlement communication, as vividly as they like, and then delete it from the communication and sit there while they yell at me about it until they get it out of their system and agree to the firm, but non-gratuitous, letter. Indulging in the saucy wink — or reacting to it — enriches nobody but the hourly-paid lawyers, who are the coffin-makers of this particular O.K. Corral.
As a result, sometimes it seems like I spend a lot of my professional life getting yelled at. They don't teach you about that in law school.
(Note that some lawyers favor communicating "holy shit, my client is crazy" to the other side, in order to encourage a better settlement, on the theory that the other side will conclude they are not dealing with a rational actor and adjust their settlement tolerance accordingly. That's swell, if you can reliably depend upon the rationality of the other side. But often humans don't react by saying "the other guy is irrational, which is going to make trial much more expensive, so I'm going to improve my settlement offer." Rather, they say "You think you're irrational? I'll show you irrational!! WHARRRBARGLGL!)
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