You know, wealthy people don't like me.—Donald Trump, at the Republican National Convention, 1988
If I ever ran for office, I’d do better as a Democrat than as a Republican—and that's not because I’d be more liberal, because I’m conservative. But the working guy would elect me. He likes me. When I walk down the street, those cabbies start yelling out their windows.—Donald Trump, Playboy, 1990
How stupid are our leaders?—Donald Trump, Trump Tower, June 16, 2015
Donald Trump delights in keeping people guessing. As he expressed on Twitter, “I love watching these poor, pathetic people (pundits) on television working so hard and so seriously to try and figure me out. They can’t!” Any astute observer of the president's political style, from the journalist to the scholar, confronts an irony as remarkably grand as the tycoon's real estate holdings. With a net worth of $3.1 billion, the president declares himself a protector and champion of working-class Americans against elites of all stripes. Throughout his private-sector career and now as president, he takes pains to disassociate himself from, if not consciously rebel against and antagonize, the economically well-to-do, insisting that he is an outcast among their ranks. Such rhetoric dates to three decades ago. When CNN's Larry King asked him if he were a George H. W. “Bush Republican” at the 1988 GOP Convention in Houston, Texas, Trump sanguinely replied “no” and maintained that
The people that I do best with drive the taxis. You know, wealthy people don't like me because I’m competing with them all the time. And I like to win. I go down the streets of New York and the people that really like me are the workers.
His perspective has changed little since. As he flirted with a run for the White House in 1999, Trump said, “Rich people who know me love me. Rich people who don't know me hate me. The working man loves me.”
During the 2016 presidential campaign and well into his first two years in office, Trump vigorously celebrated ordinary Americans—the middle class, blue-collar workers, manual laborers, and farmers.