His early works were good, GWSH was not. His Rolling Stone writing was usually good, but after 1980 I lost complete interest in him.
His more recent columns - and I mean over the last several years - were banal and atrocious. In fact I recently checked some of his ESPN material and it was flat-out unreadable.
It is true however that his early and better writing was inspired to some degree by Mencken, HST said that himself. Most of the better social commentators will say the same.
He had been saying for many years that he no longer wanted live....and he wrote about it as well.