So, in preparation for talking about the latest “Tropes vs Women” episode, I’ve decided that I need to talk a bit about what I see, at least, as intellectual charity, especially since it seems that many people get confused about that, so much so that they decide that they don’t want to or don’t need to do it. This, I think, is because most people see it as interpreting the arguments of your opponents in the strongest way possible, which then can look like apologetics. At a minimum, it can easily look like you’re reading into their argument things that aren’t there in order to make the argument stronger, or to look like it’s saying things that are more “normal” than they are. Thus, it fits into the notion of “steelmanning”, where instead of reinterpreting the argument in such a way that it’s easier to defeat, you reinterpret in its strongest form (and, in my observation, it seems to be the case that almost everyone who actually says they’re steelmanning doesn’t actually manage to do that). So, at the end of the day, when you interpret charitably you make the argument look stronger, and often make it look stronger than it really is.
This is not what it means to interpret charitably. Interpreting charitably, at its heart, in intellectual pursuits is to interpret what someone is saying in such a way that, essentially, you don’t jump to any unwarranted and unevidenced conclusions about what they’re saying. So you always try to interpret what they’re saying in such a way that it makes the most sense, given what they believe and what they’d be likely to argue. To me, there are two big principles in play here:
1) Always interpret what they’re saying in line with what they ought to believe given both their words and their overall philosophical position. In short, always interpret them as consistently as you possibly can. This causes problems for a lot of Internet debaters because their primary argumentative method is to find a seeming contradiction in their opponent’s position and then declare victory based on that, which means that when someone points out another interpretation that isn’t contradictory they get upset at the reinterpretation. But in general most people will not hold contradictory positions knowingly, so either there is a contradiction there that they need to work out — and they’ll always be able to bite the bullet and take one side or the other — or else your interpretation is incorrect and they didn’t really mean that. We can see this in Kant, actually, because in his first edition of “The Critique of Pure Reason” it looked at times like he was advocating for an Idealist position, so he added a section later that explicitly refutes Idealism, and insisted that he wasn’t advocating for Idealism. At that point, you can’t just accuse him of being an Idealist and having a contradiction in his position, clearly. What you can try to do is show that those sections only work if one is actually an Idealist, and no other position could accommodate those ideas. Fortunately for Kant, this is probably not true for him.
What this doesn’t mean is that this sort of interpretation always has their argument come out looking better. All you’re doing is interpreting it in the way that best fits their overall philosophy. This doesn’t mean that they necessarily come out looking less extreme or more mainstream or whatever. For example, if you interpret Rand charitably you can blunt arguments about “It’s really in your best interest to allow this sort of regulation” because while Rand is, in fact, very much opposed to government regulation she opposes it only because she thinks that it doesn’t benefit her to have it, and thus in those cases if you could prove that she’d have to accept that that sort of regulation should happen, which thus makes her view seem less extreme. On the other hand, a charitable interpretation of Rand would indeed say that if someone gained no benefit from helping someone else, they would be permitted to completely ignore them, even to the point of letting them die, which is a pretty extreme position (given what Rand says elsewhere, you can’t go so far as to insist that they’d be morally obligated to ignore them, but at a minimum they are not morally obligated to help). The same thing applies to Utilitarianism. It’s a charitable interpretation of Act Utilitarianism to say that it would have to countenance killing someone if that had the most utility, an extreme position, but it’s also a charitable interpretation to say that it has to be based on the knowledge that the person actually has and not on some kind of idealized determination based on all possible knowledge that anyone could have, which is a less extreme position.
2) Where allowed given the considerations of 1), always prefer less extreme interpretations to more extreme interpretations. So, to use a Stoic example, you don’t insist that they have to be eliminating even those emotions that we don’t feel — ie calm passions — when their focus is on the felt emotions and the link wouldn’t have been known at the time. Applying this principle will, of course, almost always involve making the view look more reasonable as it always makes it look less extreme, but applying this principle avoids arguing from rhetoric and often arguments from strawmen, where what you do is expand the view to its most extreme possible interpretation and point out how ridiculous it is. This does not mean that you can’t use argumentum ad absurdum, as long as you show how the absurd conclusion follows directly and necessarily from their position. So don’t conclude that when they say “X is this” that they necessarily mean “All X is this” if a) you can interpret it as being “Some X is this” and b) saying “All X is this” is an insanely stupid argument, unless by their own positions “All X is this” is more reasonable.
Note, of course, that for all of these the actual words of the actual people always trump any charitable interpretations; if they actually say “All X is this” then take them at their word. But interpreting charitably means interpreting in a way that is most consistent with their positions, and so is interpreting in a way that is most likely to be true. And in any give and take with anyone, you can always learn if your interpretations are right or wrong.