Why was the '88 Dem field so weak?

[Vepres]

I'm guessing many prominent Democrats excepted Bush Sr. to easily win in both 1988 (which he did) and 1992 (which he didn't) and thus they decided against running what they thought would be a futile race.

No, actually; Many Democrats saw 1988 as leaning in their favor, for reasons probably known to you (Iran-Contra, National Debt, etc.), but all of their good potential candidates, Biden, Cuomo, Hart, all had either shot themselves in the foot or decided not to run. 1988 was probably going to go the Republican anyway with either of those candidates, but many expected the Democrats to win.

I agree with you about the factors that favored the Democrats in 1988, but you forgot to mention two very important factors that favored Bush Sr. that year: the good economy (unemployment that year was between 5 and 6% pretty low/average levels) and the fact that the U.S. was not involved in any foreign wars. These two factors greatly helped Bush Sr. overtake Dukakis's lead throughout the fall, when many people began to pay more attention to the election (and the economy and foreign affairs). I know Dukakis's mistakes greatly hurt his campaign, but I think that Bush Sr. would have had a very large boost in his support and popularity throguhout the fall (possibly enough to win the election) regardless of who his opnent would have been.

Ah yes, but I figured you knew the figures already. I think that the weak field, however, wasn't so weak after all, just that most people made mistakes. Dukakis had a 19-point lead at the end of his convention, (just forgot that, but it was probably an outlier anyway) so I'm not sure if it really favored Bush. I've always agreed with the notion that no one really starts paying attention until Mid-September, though. I do think that Bush was hard to beat, and that no one in the field really could have pulled it off.

I actually think the Democrats had a good group of people; and that at least at first, it seemed possible for them to win. During 1987 Reagan's approval hovered in the fifties, so maybe that led to some running.

A better question IMO is why was the Republican field so weak in 2000? Outside from Bush and McCain, there weren't any solid candidates that really stood a chance. Liddy Dole doesn't count, really, and Orrin Hatch couldn't win.

Republicans in 2008 and Democrats in 2004 were arguably worse.