Speaking of 2000, I’ve been thinking a lot about this shrewd insight from @adriennemiller’s recent memoir: 
DFW was on a brilliant run as an essayist at the time, and I still remember going to Bulldog News to get Rolling Stone and read the McCain essay that was already generating a great deal of praise.
After a substantial time investment I was shocked to discover that the essay was...not good. Just another Bruni/Fineman style ride in the tire swing in better-turned prose.
The key point here is Miller's explanation for *why* it was bad, an obsession with Masculine Authenticity that was shared by most of the political press.
But what's REALLY weird is that the press (although not DFW) then projected this masculine anxiety about McCain, who was at least was an actual war hero, onto the callow Phillips-and-Ivy League educated failson of a president once he beat McCain in the primaries.
This bizarre stuff about Bush being a Real Man Comfortable In His Own Skin and Gore Practically Being A Woman structured campaign coverage to an extent it's almost impossible to convey to anyone who wasn't there. MoDo the Sunday before the election that blew up the world:
(As an aside, the idea that Al Gore was so dishonest and corrupt he would accept the presidency even if he lost the popular vote but won the Electoral College was also a popular media discussion that instantly vanished from memory as soon as the shoe was on the other foot.)
To end on an optimistic note, when the GOP actually DID run McCain he *didn't* get very favorable media coverage because Bush fucked things up so badly it was hard to pretend that the presidential election was a no-stakes event you could use to work through your Mommy issues.
The fact that Bush left his Potemkin ranch for the Dallas suburbs about 3 seconds after the 2008 election is something that should have caused a lot of media introspection but didn't
