How do we resolve this paradox in free speech?
Yes, I still have major concerns. Positive discrimination, on the basis of race, is racist. If we want to help people out of a hole, we should help the people in the hole. Not the population of people who look like the people in the hole. It's not like we don't know how to identify the people actually in the hole and, to the extent the populations overlap, doing so would also have the desired affect on whatever correlated racial group.
But don't rebut that, it's beside the point. The argument I'm trying to make is an argument
about arguments. Seems to me, people have a lot of difficulty being charitable to their opponents. It's too easy to profoundly misunderstand each other. I don't trust your hubris on this, that you would do more good than harm as Grand Curator of ideas. I have the same hubris and I don't trust it in myself either. These utilitarian calculations you're doing are impossible. Freedom to express earnestly held ideas and beliefs just seems foundational to the human condition to me. You need a really really good reason to suppress that and hurt feelings don't even come close. I'm a meta-ethical utilitarian and, like you, I've done the calculation. But, I emphasize, it's not that I'm correct. It's that self-righteous meddling is an indulgence that should be held in check.