How did Gore not win comfortably?

[Guderian]

It's hard to "win comfortably" after your party held the White House for 8 years. Neither party has a lock on the presidency, partisanship is strong and independent voters are likely to be fatigued after two terms.

Even Bush's win in 1988 wasn't all that comfortable. He was trailing Dukakis deep into the summer and really his electoral victory seems very impressive only because he pulled off an ungodly number of tight wins (California, Illinois, Pennsylvania - just to mention the big states, all won with about 51% of the vote). Shuffle Dukakis and Bentsen on the ticket and you have a true cliffhanger election.

[Guderian]

Well, yes my point was that the question should be "How did Bush win comfortably" instead of "How did Gore not win comfortably". Democrats were definitely seen as bigger favorites in early 1988 than they were in early 2000, given the normal cyclical way politics usually work. Bush got lucky when Gary Hart self-destructed and Dukakis won the primaries. Gore also got a bit lucky since he faced W instead of McCain, but overall W was still a much stronger candidate than Dukakis.