I think it was a mistake by the Clinton campaign to put a white male billionaire in the front row. The much better choice might have been a veteran, or at least a representative of one of the groups Mrs. Clinton purports to champion.
I think it's true that Mrs. Clinton gained sympathy, but I think that she also lost some women when she went on national television and called Lewinski, Jones, Flowers, et al, liars, and subsequently used the phrase "Vast Right Wing Conspiracy" to dismiss their claims out of hand. Using that phrase again in the campaign has probably also been a mistake.