In his New Yorker article, “Donald Trump’s Sales Pitch,” James Surowiecki shares some salient thoughts about white working-class support for Donald Trump:

Donald Trump’s campaign slogan is “Make America Great Again!” A better one might be “Only in America.” You could not ask for a better illustration of the complexity of ordinary Americans’ attitudes toward class, wealth, and social identity than the fact that a billionaire’s popularity among working-class voters has given him the lead in the race for the Republican Presidential nomination. In a recent Washington Post/ABC poll, Trump was the candidate of choice of a full third of white Republicans with no college education. Working-class voters face stagnant wages and diminished job prospects, and a 2014 poll found that seventy-four per cent of them think “the U.S. economic system generally favors the wealthy.” Why on earth would they support a billionaire?
Part of the answer is Trump’s nativist and populist rhetoric. But his wealth is giving him a boost, too. The Democratic pollster Stanley Greenberg, who’s published reams of work on white working-class attitudes, told me, “There is no bigger problem for these voters than the corruption of the political system. They think big companies are buying influence, while average people are blocked out.” Trump’s riches allow him to portray himself as someone who can’t be bought, and his competitors as slaves to their donors. (Ross Perot pioneered this tactic during the 1992 campaign.) “I don’t give a shit about lobbyists,” Trump proclaimed at an event in May. And his willingness to talk about issues that other candidates are shying away from, like immigration and trade, reinforces the message that money makes him free.
Trump has also succeeded in presenting himself as a self-made man, who has flourished thanks to deal-making savvy. In fact, Trump was born into money, and his first great real-estate success–the transformation of New York’s Commodore Hotel into the Grand Hyatt–was enabled by a tax abatement worth hundreds of millions of dollars. Yet many voters see Trump as someone who embodies the American dream of making your own fortune. And that dream remains surprisingly potent: in a 2011 Pew survey, hard work and personal drive (not luck or family connections) were the factors respondents cited most frequently to explain why people got ahead. Even Trump’s unabashed revelling in his wealth works to his benefit, since it makes him seem like an ordinary guy who can’t get over how cool it is to be rich.

Surowiecki goes on to point out that Trump’s ‘winner’ image is packaged in a veil of distractions, since his business losses have included four bankruptcies, which he shrewdly projects as biz as usual for a courageous, visionary entrepreneur. “…The businessman he most resembles is P. T. Barnum…Barnum’s key insight into how to arrest public attention was that, to some degree, Americans enjoy brazen exaggeration. No American businessman since Barnum has been a better master of humbug…”
Surowiecki says it is “highly-improbable that he could ultimately win the nomination.” Yet “his bizarre blend of populist message and glitzy ways” resonates well “with precisely the voters that any Republican candidate needs in order to get elected.” As Greenberg says, “Trump is a huge problem for the Party. He’s appealing to a very important part of the base, and bringing out the issues the other candidates don’t want to be talking about.”
Democrats have known at least since FDR, and later JFK, that working-class voters don’t care how much money a candidate has, as long as the candidate seems honest and unafraid to support bold policies that can improve their lives.
Trump gets credit for being honest, just because he has no filter between his brain and his mouth, and that makes him look candid in comparison to his equivocating opposition, all of whom seem to be beholden to one sugar daddy or another. But that’s only part of what is needed to get elected. When the novelty fades, and Trump is held accountable to explain how his policies can benefit working people, that’s when he will tank as gloriously as he has risen.