Quite the opposite, H.L. Mencken was an old-school conservative (basically libertarian) opponent of FDR and the New Deal. He certainly wouldn't have had any use for Clinton or Obama, being an enemy of both political cronyism and the welfare state. I doubt Mencken would like any contemporary politicians very much either, including Trump, since he disliked demagogues and was wary of mass movements in general, for better or for worse.
His contempt for humanity is palpable.
That much is true. Mencken saw himself as America's version of Friedrich Nietzsche.
On the Friedrich Nietzsche point, I think Mencken would find in Trump strong parallels to Nietsche's "Super Man" concept -- given Trump's career across many fronts: real estate, hotels, golf courses, television, publishing, and now politics.
Thanks for the information, but it’s very difficult for me to reconcile that contempt with libertarian thoughts. Nietzche is also someone whose thoughts sound very liberal/progressive, mostly I guess because of the amorality.
I’m more of a St. Thomas Aquinas, kinda gal. A philosophy student that I met once told me that Nietzche saw himself as a Protestant Aquinas. So I guess even the intelligentsia don’t think entirely for themselves. Then they condemn people who support those who either think like them or can communicate successfully to them. Wah!!! Buncha crybabies ;)