I knew the 2004 election was lost after the Republican convention. Bush's ideas were bad, but had some semblance of initiative after Kerry's mostly vacuous DNC speech.
I don't like to think Kerry deserved what happened to him, but he walked right into his worst mistakes. The famous "I voted for it before I voted against it" line was in response to a heckler that he continued to engage in a civil manner. The inevitable attack ads never sat well with me -- a cheap flip-flopping charge enhanced by poor civics knowledge of Senate proceedings.
This is all pretty quaint by 2015 standards, but Kerry was often caught flat-footed, and I wonder how much of that fell on his campaign advisor, Bob Shrum (who should have been better prepared after being atomized by three Bush campaigns). His fingerprints are all over that campaign, a typical mealy-mouthed, middle-class appeal to reasonability, moderation, and an aversion to strong ideological issues. Kerry was already branded a radical early in the campaign, tried to appear above petty politics, let it stick, lost control of the message to the Republicans and/or demagogues like Michael Moore, and ran a mostly dispassionate campaign until the end.
Bush's "ownership society" imploded pretty quickly, but he managed to appoint Alito and Roberts.
