So the use of Facebook data was lauded as genius and now isn't. [1] Now you got me curious if the media would be saying all the same things if Cambridge helped the other candidate get elected.
Ben Shapiro is disingenuous by isolating Facebook data only. It's the combination of illicit Facebook data + fake news + Russia's APT that is at the heart of the problem. The fact that Facebook was warned about this and didn't work to solve their share of the problem is why they are criticized.
Disinformation of the public and spreading antagonizing rumor as fact was not invented yesterday. Assume all allegations and rumors are true, ride with it and see who looks more genuine.
Trump was destined for winning. His allure is not based on respect but grandiose dreams embedded in a nostalgic slogan. Without a politically-loaded surname he took the media by the balls and rode with it.
My best guess as an outsider is that he found people apt at selling stuff and sold to the public he was. Personal defamation ("grab them by the", buffoon, meme-made-president) is a minuscule issue in the eye of the public compared to a classified information leak scandal, "Don't forget Benghazi" and poor health rumors.
Hillary IMHO was counting on an idealistic, emancipated America when the people were rather leaning towards isolationism and making America greater than the competition.
You're mostly right, I think, but I never actually heard Clinton articulate a theory of why someone would vote for her. Everyone had their own personal reason to vote for (or against) her, which one supposes is emblematic of our long-tail data-driven time, but did she ever come out and say e.g. "this is my vision of an idealist, emancipated America"?
I agree with you that such a vision is kind of a hard sell when compared with "Build the Wall!", "Lock her Up", and "Jobs!". Only the last of those base slogans ever appealed to me (not enough to make me vote for the cretin!), so I'm not disappointed that it's the only one that has happened so far.