It's hard to believe but it is true that Mencken did not mean George W. Bush. H.L. Mencken said
As democracy is perfected, the office of president represents, more and more closely, the inner soul of the people. On some great and glorious day the plain folks of the land will reach their heart's desire at last and the White House will be adorned by a downright moron.
and many people believe this describes George W. Bush. (h/t to Zoey & Me) If you believe GW to be the everyman cowboy just off the Texas Ranch I guess you are closer to Mencken's opinion. Except that Bush (and not the Kennedys) comes closest to what could be considered an aristocracy in this country of just about any politician in the last 60 years. What Mencken was lamenting was the very American idea that anyone can grow up to be president. He called the middle class the 'booboisie'. Mencken was an elitist, and if one remembers that Bush was born in Newhaven Connecticut, educated at Andover, Yale and Harvard, and is distantly related to Queen Elizabeth, one can see our Bush is definately one of the elite.
Mencken would have been opposed to Bill Clinton. He would have approved the ascendency of both of the Bushes.