The analogy of 2000 is much better than 1960. The JFK/Trump comparison does not fit very well. The only things they have in common is their interest in lots of women and the status of a billionaire. Thus JFK won the PV, though very narrowly.
I seem to recall a situation involving Alabama's votes putting the nationwide PV vote in doubt. Basically votes were counted for Kennedy that should have gone to an indy Dem slate or something like that.
Btw, the comparison of the running mates also fits well: Dick “the warmonger” Cheney is somewhat comparable to Pence, who also stated that W’s VP is his role model. Both were mainly picked due to their congressional experience, that the nominee lacked. Lieberman and Kaine are also comparable: Both centrist Democrats and more of the “calm, nice guy” sort.
