Avoiding the Saucy Wink

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!)

Last 5 posts by Ken White


  1. says

    > 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.

    Nice to see that I'm not alone.


  2. Stephen says

    " Rather, they say “You think you’re irrational? I’ll show you irrational!! WHARRRBARGLGL!"


  3. d-day says

    I was talking to a guy the other day who had a court-ordered mediation deadline, so they went even though the lawyers had almost hashed out terms. The mediator insisted that it was more "cathartic" for the parties to meet face-to-face and talk, rather than separate rooms. He could not be talked out of it. The defense lawyer is now in the process of making a tidy profit on a getting an otherwise worthless case case ready for trial.

    (Self-important mediator + insurance defense behavoir incentive wackness = Plaintiff lawyer with occasionally legitimate gripes)

  4. d-day says

    Duh. Just clicked on link and saw that happened to you too. WHY must mediators insist on the face-to-face? Is there some double-secret mediator handbook for random screwing them up?

  5. says

    You are far from alone. I had a case with a (rather expensive) mediator who insisted on a face-to-face session that did nothing but drive the parties further apart and leave everybody upset. Both opposing counsel and I told the mediator that was what would happen, and it did, and instead of settling the case in three hours we settled it in eight.

    The part of it that really iced me was that both of the lawyers — who hired this guy in the first place — didn't want to do the mediation this way, but no, no, no, I'm the mediator and I've not only been through the training at the Strauss Institute at Pepperdine but I'm one of the trainers there, so I know better than you guys what your case needs to settle.

    And afterwards, he insisted that the face-to-face session had done some good because the parties now understood where the other was coming from. The way I saw it, they'd known that when they'd started and the case still was going to come down to the defendant's ability to pay so as to avoid the extraordinary costs of future litigation.

    The irony is, this guy is also one of the more aggressive e-mail spammers and direct mail marketers of any neutral I've ever worked with, either paid or free.

  6. says

    TJIC – Be strong, my man. And Ken's advice is good advice, no matter how much you'd like to wink at them, just do what you have to do to win – there is no better vinidcation than winning. A saucy wink doesn't even get close.

  7. says

    Oh, and Val Kilmer was awesome in that role. Sincerely, absolutely awesome. As far as the way Kilmer played Holiday, Ken descrined it well:

    Indifference, amusement, and a bit of sociopathy. My great Grandfather knew Doc Holiday (and Wyatt Earp, too) quite well, and from the stories I've gathered (third hand, I never met the man as he died before I was born) that more or less describes Doc in a nutshell. He wore a thin veneer of a refined southern gentleman, for purposes of amusement rather than any genuine desire to be seen as such, while at the same time being a hard drinking, hard living total son of a bitch who never murdered anyone but would sure kill on the slightest premise. A more loyal friend you'd never earn, and a more terrible enemy, likewise. Doc didn't go around making enemies as a rule, but he'd jump into a fray just for the kicks of it if given a chance.

  8. Dyspeptic Curmudgeon says

    Here's one method of dealing with the clients who have an irrational attitude (well, duh, that's ALL of them, near as makes no difference!). Take them to the nearest law library. Show them the racks of law reports.
    EVERY reported case is the history of a mistake.
    You do NOT end up in front of a judge unless *someone* has made a mistake. A mistake which has turned an error into a financial sinkhole.
    It might be that someone is mistaken about the facts.
    It might be that someone('s lawyer) is mistaken about the law which applies to the facts.
    It might be a combination of both.

    And the PERSONS in the room who know the LEAST about what happened are the ones who will decide, one way or another.
    WHAT IS THE (opportunity) COST TO YOU IF YOU ARE WRONG? Get NOTHING to defray your actual damages? Pay lots more than you think the actual damages are? Pay lawyers lots of dollars to scrabble over the entrails of something you already know and understand?
    (And where there are loser-pays rules: Pay the OTHER lawyer TOO! on top of the damages you didn't get/damages you had to pay.).

    What will you settle for now?

  9. John David Galt says

    I really believe we'd be a much healthier and happier society if people who feel that strongly about their cause were still allowed to challenge their opponents to a duel, winner take all. If the other side says no, it shows they're rational enough to make negotiating worthwhile, even if you (the challenger) are not.

  10. Gordon says

    Excellent post. Only wish I had that advice beaten into me a few years ago when dealing with my wife's partner in medical practice. would have saved us north of 150K. It seems I have an over-developed lizard brain.

  11. Rich Rostrom says

    People want to be vindicated – and they really want not to submit to deliberate injustice. Or to admit to fault.

    Yes, this can be irrational. A lot of recent Middle East history becomes clearer when one understands that Arabs often abandon rational risk/reward thinking for honor/shame thinking. Better the drastic material consequences of defeat than the intolerable humiliation of admitting weakness or error.

  12. Dan says

    So much truth here.

    1. My only successful mediations have been of the shuttle type

    2. I have on multiple occasions said in no uncertain terms to opposing counsel "holy shit, my client is crazy" AND "holy shit, the partner (that I report to) who is running this case is crazy" – opposing counsel usually just said "yeah, we know" to both

    3. Billy Zane and Jason Priestly should be in more movies together

  13. Mike says

    I was at small claims court with my wife for some billing issue. She carefully gathered all the papers that proved we were right over many hours. While we were waiting we saw another person who was being sued. The judge told her that since the other person hadn't shown up he would just rule in her favor. So she said "no" she would be fine to wait another few hours. We both laughed quietly about that. Why would you wait when you've already won. Then when it came to our turn the other person had an incomprehensible argument that amounted to she just "wanted respect" so the judge said he would settle it with no money if we agreed. Then my wife said "Wait" I still want to present my documents and case. So even immediately after laughing at someone for not just accepting a win you can still not accept a win for your sake because you want to "prove you're right." sigh.