The problem is in one of your initial premises when you said "Bob is not a deplorable."
He is.
In 2016, although all the signs were there and people
really should have known better, I can kinda give a pass to (some of) the people who voted for Trump because they have traditional conservative values and didn't believe that Trump could possibly be
that bad.
But in 2020 and
especially in 2024 (after we know what happened on January 6, 2021), everyone who still supports Trump is a deplorable, full stop, no exceptions. If anyone is voting for Trump now, they are at best wildly ignorant and/or misinformed and at worst fully on-board with turning the USA into an authoritarian Christofascist theocracy. The past eight years have made it abundantly clear that there are WAY more racists, misogynists, and bigots in the United States than any of us assumed. They're not reluctantly voting for Trump as the lesser evil candidate; they're full-on embracing Trump because he's selling them a vision of the future they want.