Covering Trump’s Long Flirtation with the Oval Office

Billionaire Donald Trump laughs while speaking to a crowd at the 2011 Palm Beach County Tax Day Tea Party on April 16, 2011 at Sanborn Square in Boca Raton, Florida.

Welcome to Politics Bites, where every afternoon at It's A Free Country, we bring you the unmissable quotes from the morning's political conversations on WNYC. Today on the Brian Lehrer Show, Kurt Andersen, host of WNYC's Studio 360 and founder and former editor-in-chief of Spy magazine, discussed the ups and downs of Donald Trump—and of covering Donald Trump over the years.

Same old song

The first thing you should know about Donald Trump's presidential run is that it's not his first. Not by a long shot.

At least twice before, Trump has gone public with his intentions for the White House, before the 2000 and 1988 elections. Kurt Andersen said that track record of false starts should raise red flags for anyone taking The Donald seriously this time around.

Back in 1987 he was flirting with the idea of running for president and saying, 'Of course, if I ran, I'd win.' And this is in the 1988 election, almost a quarter-century ago. Just as he's been bankrupt many times, Trump has flirted with running for president many times...If he dropped out, what would his excuse be? The boy can cry wolf only so many times.

Elite populist or popular elitist?

Andersen marveled at Donald Trump's love affair with the Tea Party, considering they bill themselves as a populist uprising against political, social and economic elites. Is there anything more elite than a New York City-based real estate tycoon with a prime time television show? Hence, the confusion.

In American history there's been a kind of populism that talks about how they hate the elites, and embodies hatred of elites; and here is this guy who was born rich, went to an Ivy League university and is a billionaire, and miraculously, because this is America, he's riding that middle class, working class resentment of elites. People respond to that, and he's a guy who you might overhear angrily ranting about things in the deli in the morning. He said on ABC News last week, 'I don't like rich people, I get along better with middle class and poor people.'

Minding his business

Many callers expressed solidarity with The Donald because they trusted such an accomplished businessman to do a good job turning around the national economy. Andersen disagreed that Trump's resume made him qualified for the job, and said that a detailed look at the magnate's financial history would hobble his image as a consummate business whiz.

Once people look closely at his career and these serial bankruptcies, and creditors feeling ill-used, I think that idea of, 'Oh, he's a businessman with business experience,' well yeah, and he has a lot of money, but I don't think the ways he's managed to amass and keep his fortune will bear the scrutiny of an actual candidacy.