There is an understated thesis in this piece that is voters respond to IMAGE and EGO.
Think about this in terms of your (or most peoples') egos. Would it feel worse to be called greedy/immoral, or to be called immature/naïve?
I think Hillary's campaign was banking (no pun intended) on the belief that what matters to voters is that the candidate is tough, crafty, and above all, knows how the game is played. It might not go so far as to be advantageous to be called "Machiavellian," since that would make voters think they are the targets (though we are).
She showed this by partnering with Wall-Street bankers. Wall street IS the game, in a large measure. SECRET speeches show she knows you don't show your cards; as my brother said, "Of COURSE she said there's one position you have in public and another you have in private. That's how it works!" The common voter is supposed to think, "Wow, secret talks with top game-players? She must be getting things done."
How often have you felt, (or believed you were expected to feel) awe for these higher-ups, their esoteric meetings, rules-of-order, executive committees, etc. Weren't you impressed? Or at least cowed?
Then Bernie comes along and says what should be obvious--but it isn't nuanced. And because of all this political image-grooming, you know you are expected to think, "It can't be that way. That's too simple. Why is he talking to us little people about what's right and wrong with the financial elite? Why doesn't he broker deals and meet with the Titans of Industry to shape the way things are?
We've been trained, people. We've been trained to think that if something makes sense to us, who are immature, it must be too simple. We're so naïve (as are the few politicians who are on our side) that we're relegated to sitting back and admiring the craft, the deal, the wonk.
It may be more clear with war. Pacifism is simple-minded and idealistic. Idealists are immature and naïve. Realists know there's a lot of evil out there, but they also know the best way to deal with it is to work with it, not against it. Realists know you have to break some eggs, kill some civilians, bomb some hospitals. Give away a few trillion dollars to white-collar felons.