Note that there are a bunch of "sometimes" in that statement. As much as I tend to qualify my statements in the interest of accuracy, that's not what's going on here. Those are very specific "sometimes," with implications for communication.
A couple of my friends commented in response to "On the Utility of Dicks" that they were simply dicks. As much as I love them, and I do, that's not really helpful--or meant to be. Being a dick in general (which is overstating their behavior anyway) doesn't communicate anything except that you're a dick. It stops being a tool when you can't put it down. At that point, it becomes just one more thing keeping your hands busy when you could be doing useful work.
If your dickishness is going to help you communicate the values of skepticism, it has to relate, directly and immediately, to the circumstances that warrant anger. If it isn't suited to the context, or if others can't see how it's suited to the context, it communicates nothing.
But there's another problem with wielding dickishness as a tool. This:
On the one hand, okay, but on the other hand, as a general rule, the other side is not arguing in good faith. They are having fun toying with the skeptics, making them work hard for no real gain. To them, misbehaving is fun. When their current scheme falls apart, they come back with another one. None of them actually believe what they have faith in.
I'd say very few if any holds need be barred when dealing with the "gotcha" questions true believers so often think they cleverly can get by with.
Life is too short to waste on the "gottcha" folks. Ridicule is all they deserve.
Now, before I talk about why that's a problem, let me provisionally endorse this statement from PZ Myers.
Talk to us 'dicks' sometime, and you'll discover that when we get in someone's face and rip into them hard, we already know that we're not trying to convert them to our way of thinking. We actually are smarter than that.
What we're doing is having a gladiatorial match for the benefit of the spectators. Our goal is to show how bad the other guy's argument is in a public demonstration. And that's a good strategy, because no one wants to be that other guy.
That is exactly what we think we're doing. It is even, for some variable but large percentage of the time, what some of us are actually doing. The problem is when we get it wrong. And we will inevitably get it wrong.
What's the difference between a charlatan and an example of skepticism's own Eternal September problem? That's the critical question in deciding how willing you are to decide that someone "deserves" bad treatment.
What's the difference between someone who engages in an argument in bad faith in an attempt to spread their views and someone who has internalized the views of such a person but is willing to find out what might be wrong with them? What's the difference between the willfully ignorant and the miseducated? What's the difference between someone who is out to demolish our credibility and someone who doesn't know yet whether they can trust us? What's the difference between someone who's setting out to obfuscate and someone who hasn't been trained to argue through a proposition to find the truth?
There are a few clear answers to that, but none of them are going to be clear to me in the course of an online discussion with someone I haven't encountered before. They all involve motives and history that I'm not privy to. If I'm playing to an audience, that audience isn't privy either. None of us can know without better evidence than that, and we should be suspicious if we think we do. We should be all the more suspicious as engaging in the kinds of battles we do as skeptics can and will change us.
I do disagree with Phil, by the way, that we're not at war. I think we are, in some meaningful ways. However, I don't think that's any kind of excuse to mistake civilians for combatants. Or to blithely act the aggressor when we're not sure. It's the easy path, but it's not hard to see why it's the wrong one.
It's also good to keep in mind that being constantly under siege, even by choice, can cause its own set of perceptual problems. I've written about them humorously, but the issue is real. One of the most important lessons I've learned in arguing online is that the word "clearly" is a flag for a bunch of bundled assumptions I haven't bothered to unpack. If I think someone is clearly being dishonest, and I stop with saying that instead of breaking my observations down to specifics, I'm cheating. I'm not doing the work. I am, in fact, being a very bad skeptic. And I see the shorthand of "clearly" used all too often in these sorts of discussions.
When I praised James Randi for being a dick with respect to the people he profiled in Flim Flam, I was praising someone who mixed extensive documentation of harmful behavior with his anger. He did the work. Anger was punctuation, not the message, and there was never any doubt that his anger and dickishness was in response to misbehavior with the potential to do even more harm than it had already done. That was effective.
I'm not Randi. The chances are almost exactly 100% that if you're reading this, you're not either. I am considered a pretty good writer, though, and I have a track record of changing minds that I'm pretty proud of, given how difficult that is to do. On top of that, I believe that being a dick can serve a useful purpose. I still don't do it very often.
Why? It goes back to the idea of civilian casualties. You can't convert a dead person into an ally. You can't convert the dead person's friends or relatives or neighbors or people who read a touching news report of the death. You can't convert, in any real way, someone who is only agreeing with you in order to keep from being killed themselves. You can't even convert someone who doesn't understand what the fighting's all about.
You can sometimes convert someone who watches you for a while and understands that you reserve your judgment and your anger for the people who will do your potential ally harm--if you can convince them you're right. That looks strong instead of merely dangerous. People like to have strong allies.
Being a dick can work, but only if it doesn't hurt us first--and if we can make sure it doesn't hurt the innocent. Or, to bring it back around and give Phil the last word, "Anger is a very potent weapon, and we need that weapon, but we need to be excruciatingly careful how we use it."