Are you familiar with the musical Hamilton? And, more importantly, the history behind it? Aaron Burr, America's 3rd Vice President who almost became the second President, spent his entire political career not taking any strong political stance. He relied on his eloquence, and charm, and on basically inventing active political campaigning.
We remember leaders with strong convictions better. Like them or not - and I have either a strong dislike or mixed feelings for everyone on your list except FDR - they stand out.
And. sure, Trump is an edge case. But Warren G. Harding wasn't a gem, either. And his presidency was absolutely mired in controversy and corruption. And that's at the presidential level. On the local level? Corruption has always loomed large. The Godfather, in 1972, portrayed senators as working directly for the mob, because some DID.
And who was a bigger celebrity in America following the revolutionary war than George Washington? He ended up being a great - if flawed - statesman, but he won the elections because he was good at fighting, as did Eisenhower, much later.
The tools of today are different, more immediate. But politicians were throwing verbal feces at each other in newspapers from the late 16th century onwards.
I would argue that Ronald Reagen was a terrible president, who suffered from dementia for much of his presidency. He won his second term by a landslide and is still considered a political god on the right. Because he had charisma, and a soothing voice, and happened to be around when the USSR was collapsing. Never mind that he willfully chose to ignore the AIDS crisis because "icky gays," or that his administration was doing shady deals with tyrants.
All of this is not to say that Donald Trump isn't a unique case. But there were very specific circumstances that lead to his win.
If the Supreme Court hadn't decided the Voting Rights Act wasn't really needed anymore? He would have probably lost.
If Russia hadn't undermined the elections through actual fake news? He would have probably lost.
If the FBI had released information about investigating his campaign when they released information about investigating Clinton's campaign? He would have probably lost.
If Comey hadn't sent that letter to Congress mere days before the elections? He would have probably lost.
And with all of that? He still lost the popular vote by 3 million votes.
So, what I'm saying here is that there was a confluence of events, some of them (the FBI's actions in particular) massively affected by the consensus that he couldn't possibly win, that lead to Trump winning.
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