I think other commenters have had a similar idea, but here's one way to say it.
It seems to me that the proposition you are attacking is not exactly the one you think you are attacking. I think you think you are attacking the proposition "charitable donations should be directed to the highest EV use, regardless of the uncertainty around the EV, as long as the EV estimate is unbiased," when the proposition you are really attacking is "the analysis generating some of these very uncertain, but very high EV effect estimates is flawed, and the true EVs are in fact a great deal lower than those people claim."
The question of whether we should always be risk neutral with respect to the number of lives saved by charity is an interesting and difficult one (one that I would be interested to know what Holden thinks about). But this post is not about that difficult philosophical question, but simply about the technical question of whether the EV estimates that various people are basing themselves on are any good.
I take your point to be that I have taken something that is really a matter of degree "how much weight should I give to the opinion of this or that person?" and turned it into something dichotomous "is this person a good guide for me or not?" Here is my response.
Let's start by imagining that you can only hear the final opinions of the different advisers, and cannot discuss with them their arguments or evidence relating to the different elements of the question. In that case, the final opinion of anyone who has a valuable insight into any element of the question ought, all else equal, to move the needle for you at least a little bit. But it may be only a very little bit, and it can perfectly well be zero. In the Chicago School example, there are categories of firm conduct that Chicago people think should basically always be permitted, but that people like me think should sometimes be permitted and sometimes not. In those cases, merely knowing the final opinion of a Chicago person about a particular variety of conduct helps me not at all. Another way to get from "X's opinion should move you a very little bit" to "X's opinion should move you not at all" by throwing in a small fixed cost of the consultation.
But regardless of whether the adviser's final opinion moves you not at all or a little bit, the point is that there can still be a lot of value in hearing their arguments/evidence on particular points. If there are things that firms do that Chicago people think should always be permitted, but that people like me think should sometimes be permitted and sometimes not, the arguments/evidence of Chicago people on specific elements of the question might be of great value in helping me figure out which ones are which. And so the original point remains: the existence of valuable advisers who are not good guides.
I don't think this phenomenon is rare at all. I think in economics alone there are many insights in many fields that are now regarded to be extremely valuable for clarifying elements of big questions, but whose originators combined those insights with a great deal of wrongness, arrived at wrong final conclusions, and nevertheless were heeded on the final questions based on their insight into the specific elements.
Nice. I particularly liked the dig at Rooseveltian machismo. Of course it's possible to go too far in the opposite direction too. Some related thoughts here.
There is a neat paper on this by Feltovich, Harbaugh, and To called "Too Cool for School? Signaling and Countersignaling."
Fantastic.
A Hassidic Jew was willing to eat pumpkin bread baked in your kitchen?
I see ciphergoth already made my first point. Sorry about that.
Landsburg's argument is sound, and I mostly follow it and occasionally try to sell others on it. But I can think of one exception, which is if the political power of an organization that you support depends on the number of members it has. So for example I pay membership dues to one organization that is not my main charity because I want them to be able to claim one more member.
And there is one place that I think Landsburg gets it plain wrong. He says*:
To please diverse stockholders, corporations tend to diversify their giving, often through the United Way. For individuals, by contrast, it really is quite impossible to justify that level of diversity. Surely among the hundreds of United Way recipients there are some you consider worthier than others. That means you can target your charity more effectively by bypassing the United Way.
But if you think that the United Way comes tolerably close to sharing your values, but you think that they have better information than you do about relative needs and competencies across different organizations, then it makes perfect sense to donate to them, doesn't it?
The point is that these are two very different kinds of valuable advisers, but the distinction is often missed.
And while I do think in real life there is something of a dichotomy between "people whose final judgment I trust on questions like X," and "people whose final judgment I don't trust but who I still want to hear what they have to say," I think a similar point could be made with more than two categories.