Donald Trump: Embracing Contradiction, Not Thinking Too Much

'He really does, in many ways, reflect what the United States is,' says Trump biographer Gwenda Blair

"For better or worse, he is someone for whom everything is transactional," Gwenda Blair says of Donald Trump. Credit: Michael Appleton/NYTimes/Redux

Gwenda Blair has had a very in-demand couple of months. Blair is the author of 2001's The Trumps: Three Generations That Built an Empire, which was adapted and re-released in 2007 as Donald Trump: Master Apprentice. Simon & Schuster is slated to publish an updated e-book this fall.

Blair recently sat down with Rolling Stone to discuss what it's been like being a Donald Trump expert during the Summer of Trump, what we can learn about the candidate from his family history and how he's trying to "brand" himself into the White House.

Why did you decide to focus on Donald Trump?
Well I never expected to be the expert on Donald Trump. When I originally set out to do the book, it was going to just be about Donald. But when I started looking into his background – his father and his grandfather – I was struck by how these three generations taken together are really a case study of American capitalism over the last century, or by now more than the last century. So I made the book about grandpa, dad and Donald taken together as a history of American entrepreneurship. I wanted to take a serious look at this very well known person who was mostly seen in the press as a figure of fun – somebody people were endlessly sarcastic about, but didn't really take seriously.

Are you surprised by this latest turn in the Trump story: running for president?
Not really. He started bringing up the idea of running for president in 1987. This is his sixth time bringing it up, and it is by far the most serious of all the times, but he long ago brought up the idea that maybe he would be a good guy to be running the country.

What do you think is behind his decision to finally run?
There are a lot of elements behind his success, starting with the fact that an ancestor in the 17th Century in Germany changed the family name from Drumpf to Trump. What a terrific name, and so much easier to work with than Drumpf in the U.S. When his grandfather came to the U.S., the name had long been changed to Trump, so we could call that lucky break number one. Lucky break number two is that his grandfather came here. Lucky break number three is that his grandfather later tried to repatriate to Germany but was not allowed to because he hadn't done military service, so the family ended up being in the U.S. Lucky break number four is that Donald's father had been a very successful builder in the outer boroughs of New York and had both the financial resources and the political connections to help Donald make his entrée into Manhattan in the mid-Seventies to begin his meteoric career. The extra booster rocket for Donald was his grasp of branding. I don't think even he could have grasped how significant that would be, but he put his name on everything he built, from Trump Tower on, and made himself a mega-celebrity and a branding juggernaut.

And I think that now he must be wondering, "What's left?" He's done more or less everything he's set out to do. He's become a global phenomenon, and the final round, so to speak, would be going after the biggest, most powerful job – seeing if his branding strategy can land him in the Oval Office.

It's interesting that he's self-funding his campaign.
How much he's spent so far, like all of his financial details, is closely held. But I think his calculus is that he can use his brand, his celebrity, that puts him on the front page every single day, in every single paper in the country, without spending a dime. He's so far put out barely any ads compared to everybody else in the race. He has an almost entirely volunteer setup, to the extent that he has any setup at all. He's always had a very, very lean operation, and his political operation is no different.

And he's using his own aircraft to travel…
Indeed, but I think those things were already fixed cost. Those were sunk costs, so what's the additional expenditure by running a campaign? Yeah, it costs something to send a helicopter up, but I think that's not much of an additional expense for him. This is a guy whose basis of his fortune is real estate. He's famous for using other people's money – otherwise known as OPM – to build things, and then sell things, and take the profits. This is a way of life that frames everything he does.

Do you have insight into him running as a Republican? He used to be a Democratic donor, and he'd said in the past that if he ran he'd do so as a Democrat.
I sometimes say I have a PhD in Trump Studies, I've spent so long on this book. I went to where his grandfather came from in Germany, I went to the Yukon, where his grandfather had a restaurant, the New York Military Academy, where Donald Trump went to school, Atlantic City and Florida, where has various enterprises are. And after all of that, I can tell you that this is a family deeply steeped in the idea that you do whatever it takes to win. I don't think it matters to him that much – liberal, conservative, Republican, Democrat. All of the negative things he's said about one or another group, I'm not sure how much those things mean to him. What he is really, really good at is listening to his audience. And his audience for this presidential run is this angry, middle American, disenfranchised, seething mass of people who feel like they've been ripped off, they haven't got what they deserved, they haven't gotten the prestige, and the respect, that they think they deserve, and somebody's to blame – some group is to blame. To appeal to that group of people, he's been very shrewd about going after all manner of other targets, and I think that's the calculus – not whether to be a Republican or a Democrat.

He's made some very inflammatory remarks about immigrants, but he has immigrants in his family: his mother, his wife Melania, Ivana…
As Walt Whitman famously said, "Do I contradict myself? Very well, then I contradict myself." I don't think he has any problem with contradicting himself. That just doesn't seem to be part of his MO.

And his recent comments about women, do those seem pretty status quo for him, based on your research?
He was always extremely courteous to me, all the times I interviewed him in his office, when I saw him at one of the places I traveled, whenever I encountered him. As he says, he has had a number of women executives working at the Trump Organization. So he has a good record with women in those respects. At the same time, again, right now he's appealing to a disenfranchised, angry group of people who think they've seen all kinds of other groups get lucky breaks and get ahead of them in all manner of ways, summed up by Donald as political correctness or affirmative action. So going after women, going after minorities, going after immigrants – it all makes perfect sense, given the audience he's trying to appeal to. Of course, in recent weeks we've seen him kind of soften the edges of those things, and if he does end up being the Republican nominee I would imagine he would soften the edges even more.

What's something you think voters should know about Trump, but perhaps don't?
For better or worse, he is someone for whom everything is transactional. Everything is win or lose, black or white. You do a favor, you get a favor. You do something for somebody, you ask for something from somebody. So far, that's been a successful business model, forever being in negotiating mode: "What do I want to get, and what do I have to give to get it?" Arguably, that could be useful in politics. But what's missing there, one might say, is some sense of larger community, of a social contract, of everyone being in the same boat, going the same direction, rowing together, helping each other out, some notion of the public realm, and the public good – public schools, public transportation, public parks – a larger whole that participants or citizens are working together to maintain or improve. I'm not sure where that is in this transactional worldview.

What's your prediction for how this race goes down for Trump? How far will this go?
Everything he's done so far is so confounding to the usual framing of the primaries, how the political process in the United States has historically unfolded. He's gone at it in such a different way – he's just turned everything upside down, and confounded all the notions of how things take place. He hasn't said to the Republican Party, "Gee, I hope you'll have me"; he's said to the Republican Party, "You better hope I want to have you!" And that is such a turnabout that it's hard to say what the outcome is going to be. A lot of people watching this, especially a lot of politicians, are waiting for him to, in some way or another, go too far.

I wonder what "too far" would even constitute.
Yeah, what does "going too far" mean? But that's the posture of his competitors in the Republican nomination: something between waiting for him to go too far, and periodically trying to give a little jab to see if they can get him to go too far. But he is the scorched-earth king. He's the comeback guy who's got some reel-able zinger ready for every time anybody says anything that might be perceived as criticism. They seem very off-the-cuff when he does it, but I wouldn't be at all surprised if they are not off-the-cuff at all. He's got these barbs ready. So anybody who goes up against him in the public spotlight, especially in a debate, who comes back at him with anything less zingy has pretty much already lost the fight, because those public spectacles are about the quick punch. They're not about thinking. Anybody who takes a while to think about an answer… which you might think would be something you'd like to have in a president – somebody who's actually considering what steps to take, what strategies might be the most effective. Thinking is something we might esteem in a president. But that's not the model that Trump is proposing, and it's not a model that plays very well on television.

Do you plan to update your Trump book again, or are you done with him as a subject?
Simon & Schuster, my publisher, is releasing an updated e-book edition that will have a new introduction. So yes, I am bringing it up to date.

You can't escape him, even if you wanted to!
Yeah, it's really been quite… Of all the things that I expected to happen, this wasn't it. But with my "PhD," I find I have a lot to draw on in thinking about, "Who is this guy and how did he get here?" It's true of everybody, of course, that their family background and their family culture determines, to a very great extent, their perspective. They may or may not embrace that family culture, but it certainly has a marked impact on them. Trump's particular family culture encapsulates American capitalism and entrepreneurship, and he is the product of that. He really does, in many ways, reflect what the United States is. The larger question is what we think about that – whether we want to vote for that, whether we think that's a good thing or a bad thing, someone who's so fixated on winning or losing, and not on a more deliberative process, and a notion of being part of a world.

What a time to be alive.
Indeed, indeed.