One of the enduring mysteries of American politics is why so many people are so supportive and admiring of wealthy people who in return have nothing but contempt for them and do everything they can to enrich themselves at their expense. Many people of ordinary means seem to think that F. Scott Fitzgerald was wrong and that the rich are like you and me.

There have been various theories to explain this, one being that ordinary people in America have the firm belief that their current state is just temporary and that they will also be wealthy soon and move in the same circles as the people they admire. Another is that they think that wealth is a measure of one’s intelligence and abilities and a sign that America is a meritocracy. As a result, ostentatious displays of one’s wealth is not something that is frowned upon and is even welcomed.

There is one exception though. Politicians running for high office tend to downplay their wealth, often dressing down and adopting a folksy attitude, sometimes including colloquial speech, in an effort to show their connection to the needs and concerns of voters.

But not Donald Trump. He goes out of his way to talk about how rich he is, even inflating his wealth. No one can accuse him of financial modesty. He misses no opportunity to brag about it and to display it. And yet, it is quite extraordinary how people still feel that he relates to them

Thanks to a tip from reader Norm, I watched a documentary about Trump called Trump: What’s the Deal? that was made for TV in 1991. The writer of the documentary Jesse Kornbluth explains the backstory of the film.

I was called in to write the piece after the filmmakers shot the footage. It was easy work, because they had remarkable stuff: Donald working with the mob in Atlantic City, intimidating tenants, hiring illegal immigrant labor, verbally assaulting his family and underlings, trying to move a Florida airport because jets flew directly over his home… the list goes on and on.

Perhaps most interesting from a political point of view, the filmmakers revealed Trump to be the opposite of a small-government conservative. He got his start with his father’s money and political connections, and he made money the same way his father did: on the backs of taxpayers.

But most upsetting to Trump was the film’s revelation that he hadn’t made as much money as he said he had. The producers were among the first to show that his financial empire was built on braggadocio… as recent reports show it to be to this day.

The documentary was made when Trump was at a low point, when his loan-based shaky financial empire was collapsing and he was forced to declare business bankruptcy and almost personal bankruptcy. Trump was so upset at how he was portrayed that he threatened legal action against anyone who showed the documentary and hence it was not aired on television. But now it has been made freely available online.

Here’s the trailer.

You can see the full documentary here. I watched it and although it lacks polish, jumps around chronologically and would have benefitted from tighter editing, it is successful in showing Trump as running a permanent hustle, using his father’s money and connections and getting rich by being willing to exploit and ruthlessly remove anyone who stood in the path of his making money, including such petty and vindictive acts as making the lives of residents in an apartment building he bought miserable so that they would move out. And always, always, inflating his own wealth and using the media to his advantage. And yet, he seems to be able to strike a chord with a large number of people that he is just like them or is one of them.

The film also reveals a somewhat pathetic neediness on his part to be admired and respected by the powerful, and yet being treated as a gauche nouveau riche who was not accepted into the high-toned old money circles to which he aspired. That must have been galling to someone who thought that money could buy anything. Perhaps he feels that running for president is his last chance to achieve that final goal, to feel that he really is somebody to the people whom he feels are somebodies.

I came across a clip in which Republican pollster and strategist Frank Luntz and Fox News assembled a focus group in New Hampshire to discuss the Republican race. It appears that as soon as Trump’s name was mentioned, this discussion exploded.

Luntz confirms what I said before, that Trump’s supporters don’t care in the least what others say about him or any disparaging things that emerge about him. They identify with him, see him as one of their own, strange as it may sound.

Bloomberg News also talked to a bunch of people who liked Trump and their comments were interesting.

They actually think that he is a rich person who cares about them, so clearly there is something about him and his message that is resonating with a considerable number of voters.

Which raises an interesting problem for Trump’s rivals. The usual things that bring a candidate down, such as scandals or committing gaffes or saying outrageous things or running out of money, don’t seem to work against him. The common campaign tactic of doing opposition research on rivals and then leaking damaging information to the media does not seem to be a viable strategy.

They can’t ignore him and hope he will fade away because he has become a media sensation and knows how to get publicity, displaying a shrewdness that shames his rivals. When he released Lindsey Graham’s private cell phone number, for example, Graham responded with an ad in which he destroyed his phone in multiple ways. This looked pathetic and invited more ridicule because everyone knows that destroying your phone would not solve the problem. But when a website released Trump’s private cell phone number in return, his camp quickly made it so that anyone who called received a welcoming message for his campaign. That’s how you play the media game.