Mr. Tutt, I have posted a number of comments on this website asking why blackface is offensive to blacks. You are the first one to provide an answer: that more than 100 years ago, some people used blackface to insult black people. I find this to be weak logic. Can you rule out the possibility that some people used blackface to illustrate the evils of slavery? Do you know if there were any plays during the nineteenth century in which white actors used blackface to portray blacks in a sympathetic light?
My guess is that nobody knows the relative degrees to which blackface was used to ridicule blacks or to empathize with them. There were, of course, huge numbers of racists in this country during the nineteenth century. There were also huge numbers of Northerners who gave their lives to liberate blacks. As you say, the history is nuanced. My version of that concept is “It’s ALWAYS more complicated than you think.”
I have a lurking suspicion that we’re tackling the problem of racism with a shotgun rather than a rifle. There are writers here on Medium who accuse all white people of racism. Some people sling that term “racist” around so readily that they dilute the term of any power. When lots of worthy white people are labeled as racist, the term loses any incriminating value. This gives the real racists cover under which to hide.
Rather than seeing racism in any gesture, every glance, every phrase, I think we would make further progress by focusing our energies on condemning the undeniable cases of racism.