The astute, ambitious lawyer who made no secret of her discomfort with retail politics called them "a basket of deplorables". She now lives to regret that remark amid the rustling of autumn leaves in her home in a picturesque hamlet near New York.
The shrewd businessman, after making a fortune in real estate and reality TV, read the mood and thrived on the visceral energy his raucous public meetings generated. Less than three weeks ago, unencumbered by his documented lack of impulse control, he closed the best deal of his life.
The media tracked every zig and every zag of every opinion poll in the 18-month drama that was the 2016 US elections, buttressing it with a continuous stream of strident analysis.
And it completely missed the plot.
The white voter in America's Rust Belt as well as in affluent suburbs has made sure he will never again be left out of political calculations in Washington.
The surprise is that the disquiet in America's hinterland as well as in its wealthy enclaves remained largely unreported until Nov 8, when the millions who saw no charm in the status quo voted to show they had had enough.
How could the grievance of millions remain invisible in a nation of never-ending news and blow-by-blow analysis? That merits a closer look, even outside the United States. Even if you are not American, you still live within reach of trends and policies that come from Washington.
One strand of that scrutiny begins at the media's door. How could professionals committed to reporting reality fail to see it?
It could be argued that the candidacy of Mr Donald Trump was so unconventional that it eluded those joining the dots in newsrooms.
But what also needs to be examined is whether the media missed the picture because it was not what it expected or even wanted to see.
This is a pitfall peculiar to Western democracies, which are split down the middle along two distinct and disparate political ideologies. Either you are a conservative or you are a liberal.
Conservatives believe in less government, more religious liberty and less taxes. Liberals believe in more government - to provide healthcare services and a safety net to poor people. They also cherish social goals such as gay rights, marriage equality and diversity, and environmental protection.
In the US, all mainstream media operates out of big urban centres. This is perhaps one reason why it is more aligned with urban causes.
Studies have found that the average American journalist stands to the left of the average American voter. It is the liberals who rule the roost at some of America's most storied media institutions - the New York Times, the Washington Post, the Los Angeles Times, CNN, NBC and CBS, among others.
For the record, the media itself vehemently denies a liberal bias, even if it is well known that most reporters are liberals. Journalists donated nearly US$400,000 (S$570,000) to the 2016 political campaign. Nearly all of it went to Mrs Hillary Clinton.
In an interview with the Financial Times, published before the elections, New York Times executive editor Dean Baquet explained the paper's anti-Trump coverage. He said: "We are used to warring philosophies, but this is different. This is a guy who makes stuff up. I am not opposed to his presidency, that is not my job. But my job is not to beat around the bush when a candidate lies."
Regardless, in its reporting of Mr Trump, the media portrayed him as a clown, treating him as being outside the accepted "sane" world view. Pre-judging him as unelectable by their own standards, they did not do him or his supporters the respect of scrutiny, except in a dismissive way.
When voters began responding to Mr Trump's pitch that he would reverse joblessness and the hollowing out of the middle class, the media interpreted the large turnouts at his rallies as expressions of misplaced angst of a majority dreading its loss of privilege.
To the cameraman and the scribe, to the reporter and the commen- tator, anxious voters struggling to make ends meet became merely the face of " white fear". They did not distinguish real grievance from the noise they associated with conservative radio hosts such as Rush Limbaugh or Sean Hannity - a chant from people on the wrong side of globalisation, technology, and indeed, history. The media blithely reported on the latest instance of Mr Trump's "buffoonery" or the next turn in Mrs Clinton's e-mail probe, continuing its pursuit of controversy.
America's conservative media such as the Wall Street Journal and the Weekly Standard were alienated by Mr Trump's assault on traditional Republican values and made no bones about their concerns about his temperament, character and suitability for office. They abhorred his personality and his insurgent outsider status.
Conversely, in their reporting on Mrs Clinton, the media easily excused her lack of connection with voters. Report after report in the New York Times and other media made wry note of her "woodenness" but with a caveat implied: "You have a tough time emoting but that's okay because you are immersed in policy."
The New York Times and the Washington Post, among many others, endorsed Mrs Clinton as the better choice. USA Today, breaking its no-endorsement policy, told voters Mr Trump was an avoidable choice because he was "unfit" for presidency.
Scores of conservative newspapers could not bring themselves to endorse this year's Republican candidate either.
The electorate disagreed. While judging him every bit as "unfavourable" as his rival, they still gave him the job.
As the media, like much of America, takes a Thanksgiving breather, I wonder if they will cover President Trump like they did Candidate Trump.
With news yesterday that Mr Trump may choose between two conservative talk radio stars Laura Ingraham and Monica Crowley as his press secretary, the White House Briefing Room is certain to be the focus of some intense jockeying. Both women are smart, beautiful and unapologetic about their politics. A reality show could not be scripted better.