Great thread. Thank you.
I cannot claim any real expertise on Mencken’s collective output, nor how that mapped to whatever was really in his head. As we’ve discussed about e.g. Tucker Carlson today, journalists, politicians, and now celebs in general, who develop a larger-than-life public persona as a deliberate act seem to eventually lose their actual personality into that act. The actor turns into the character they started portraying.
That cognitive dissonance is at the center of a LOT of, as you say, elitist thinking. Whether of the left, the right, or the libertarian whichever direction that is (down maybe?). It’s simply the nature of the “strong” in the guiding hand and in which direction it should guide the sheep that the sides differ.
The other major difference is that the rightist side has the easy downhill track. Like a car with bad alignment, raw human nature in the bulk pulls to the right and can be steered to the left only by dint of continuous education, nurturing, and wide exposure to the rest of humanity not similar to yourself. It only takes one generation of neglect to allow the crude know-nothing right-leaning state of nature to be renewed.
Whenever we discuss a historical figure their racism, sexism, and (usually) antisemitism comes up. ISTM that always needs to be graded on the curve. Someone who was mainstream in their time but outré in our own time would of course be outré if magically teleported to our era intact. But IMO a better question is if that person had been born into our era, say in the 1950s or 1960s as most of us here were, how would their views have developed?
As to my actual opinion of Mencken’s reaction to trump …
I think he totally would have started out as the OP says, repelled by the obviously stupid and venal carnival barker on reality TV.
But, like many Republicans in 2015-2016, Mencken would come to the belief that trump could be usefully ridden into the presidency where “the adults in the room” (and more importantly those in all the back rooms) could stage-manage the carnie barker into doing actual elitist “good” as seen by those elitists. He might well have endorsed and voted for trump in 2016. As did a legion of traditional Rs, both ordinary schlubs like us and prominent pols, celebs, and pundits. For just those same reasons / reasonings.
By 2019 I think Mencken’d be totally appalled as he (and lots of other R-leaning elitists and 2016 trump voters) came to realize they had a loose cannon captaining the ship of state (to badly mix metaphors). For sure post- Jan 6th he’d be in the thundering denunciation camp. Net of course of whether his continued employment and access to a bully pulpit depended on which view he espoused. Always an issue for journalists for hire.
Now in 2023 Mencken, like some commentators here, would be proclaiming the game lost, the frothing inmates so outnumbering the guards that the asylum will inevitably be taken over and quite soon. So the least bad course forward is to accept that reality, hunker down, and let the cleansing fire of raging know-nothing extremism burn itself out over a half-century or more, then try to rebuild a nice civilization upon the ashes. He might well argue that 1950s Germany was a pretty nice place, but they could not have gotten there from 1930s Germany without their own time in the cleansing fire.