Republican candidate Donald Trump doesn't like to lose. So he's likely pretty happy knowing polls show him to be the favourite for the Republicans headed into Tuesday's New Hampshire primary.

An ace on Twitter, he's been tweeting insults all week about Senator Ted Cruz, who won in the Iowa caucus Monday. Trump also launched a new ad campaign which highlights the diversity of Americans who say they support him.

Few people have studied Trump as closely as Gwenda Blair. The Chicago-based investigative journalist wrote the definitive portrait of the billionaire and his family, The Trumps: Three Generations of Builders and a Presidential Candidate back in 2000. It was updated and re-issued this past December.

She first approached Trump back in 1988 when he was already a phenomenon in New York's real-estate scene. Her thought was to write a cross-generational portrait of his entrepreneurial family. This led to numerous interviews over many years. Her timing was impeccable, charting his rise and fall and rise again over the next two decades. Now Blair has become the go-to person for insights into Trump's motivations, guiding philosophy and character.

CBC News interviewed her this week over the phone.

What first drew you to Trump as a subject back in the 80s?

Donald Trump was already a very big figure on the landscape back in 1988. He was famous for being a guy with an enormous ego. So how was he able to make that work for him? How did he leverage that into becoming his trademark? That was the original thought I had. Back then, he was already the exaggerator of exaggerators. The first factoid I stumbled on was that when he was building the Trump Tower, he didn't start the floors with No. 1, but rather with 12. So the tower sounded higher. And I remember thinking: Doesn't anyone laugh at him? But that way of exaggerating and bending things, for trying to be the best of the best, worked. He knew his market loved that.

Trump biographer Gwenda Blair

Chicago-based investigative journalist and best-sellling author Gwenda Blair wrote the definitive portrait of Donald Trump and his family, The Trumps: Three Generations of Builders and a Presidential Candidate, back in 2000. (Matthew W. Stolper/Provided/Simon & Schuster)

How unusual was it that he gave you access?

He was of the school of thought that there was no such thing as bad publicity. He was also of the school that if anyone says anything bad, you sue them. A very litigious guy. But he was also known as someone you might be able to get to.

That he opened himself up to me would be a stretch. I would come to his office with a list of questions. And he would free associate exactly as people have seen him do in speeches and in the debates. He doesn't really answer questions. That's him. Listing his achievements and referring to himself in the third person. That's who he is.

You interviewed Trump many times over the years, how has his thinking about politics and business evolved? 

He is pretty consistent, I would say. He had a grasp, whether it was conscious or intuitive, that the future was in branding. He was very media-savvy, and very media-conscious. His favourite pose was sitting behind his desk in front of a wall of magazines with his photos on them.

So what are his essential qualities, in your view?

His extraordinary ego, and psychologically, his competitiveness. Also his binary view of the world that you're either a winner or loser. He likes to be around people whom as he sees as winners. He's very respectful of athletes, of champions. That's the crowd he wants to be with. He doesn't want to be around losers. And either unconsciously or intuitively, he has a trademark look. He's always wearing a suit, a power tie, usually red, black business shoes. And the hair. The hair became his trademark, like the peacock for NBC or the apple for Apple computers.

Your biography of Trump is not flattering. You write he's motivated by "finding leverage in every situation." So what do you think his redeeming qualities are?

He is — as he reminds people always — a dealmaker. His first book The Art of the Deal is several hundred pages of patting himself on the back for being able to close deals. He is a very good dealmaker. He's known in the business community for being well prepared going into negotiations. He's a guy who knows how to use leverage, to find the soft spot where somebody is going to give in, and then exert pressure.

Cover - Donald Trump: The Candidate

Blair first approached Trump back in 1988 when he was already a phenomenon in New York’s real-estate scene. Her biography was updated and re-issued this past December. (Provided/Simon & Schuster)

Those are significant strengths, arguably, in a chief of state. He's somebody who looks to make the deal happen, who is not bound by ideology, as some of the other candidates are. That has not been Trump's M.O. He's got to win, that's for sure. But as long as he wins, he's flexible.

His comments about women have galled many people. His daughter, who works for him, says his hiring practices show he's not sexist. What are your thoughts? 

Donald Trump does indeed hire women executives, and he says he hires them because they have to work twice as hard to prove themselves. Whether that's exploitative or shows he's respectful of women's skills and talents, I leave it to others to decide. But there's a great, long list of his remarks, saying disparaging things about women. He's on his third model wife. And he's in a crowd where having an arm-candy wife, or trading someone in for a new model, is not considered a problem. These women may well be his equal and more, but that's not how they choose to present themselves in public.

His current wife, Melania, posed nude for British GQ on a bearskin rug. On another occasion, she posed on the set of a photo shoot, a mock-up of the Oval Office, with Donald at the presidential desk. Melania, wearing a very tiny bikini, was laying supine on the floor in front of the desk on a rug embossed with the seal of the President of the United States. It's a very startling image.

Trump talks about "making America great again," which is a Ronald Reagan slogan. What do you suppose that means in practical terms if he were president?

When he recycled that slogan while campaigning, he trademarked it. It's perfect for someone appealing to an older, white, angry audience that thinks everything is going down the tubes and feels ripped off and is looking for somebody to blame.

His plan for what he would do if elected pretty much boils down to "Trust me. I can do it," and thumping his chest, showing he's the alpha male who will be able to stare down, put down, dismiss anything that stands in his way. And then, once he's commander-in-chief, blast them out of the sky. That's the plan. He's very short on details.

You say his popularity hinges on a rage or discontent in America today. Could you explain that?

He's hardly the only one trying to ride that. His strategy is what has been referred to as red meat: Keep tossing it to his audience in the form of targeting or scapegoating on a pretty routine basis. The more unexpected, the better. Who knew he was going to go after John McCain? What? But look at all the headlines he got.

People didn't even consider what they were being tossed. They jumped. That carries him from day to day. He has a good read on how often you have to do that. He is the person Twitter was invented for. He can sit at home and tweet to his many millions of followers. He keeps churning it out, the insult machine. Much of the media runs on the same machine. It's all synched up.

APTOPIX GOP 2016 Iran

Donald Trump lost the Iowa caucus to Senator Ted Cruz earlier this week. But he's up in the polls heading into Tuesday’s New Hampshire primary. (The Associated Press)

Since losing in Iowa, Trump has sent a volley of tweets accusing Ted Cruz of stealing the vote in the midwestern state. Cruz accuses him of "Trumper tantrums" and "losing it." What do you think Trump's strategy is going forward to New Hampshire?

After Iowa, he stayed off Twitter for 15 hours. Then he was back on Twitter and the insults started pouring out again. He needed to be a winner. Not winning started to give him bad indigestion. He raced back to his former insult machine.  There is a danger that he would come off like a sore loser. But being a bully didn't seem to bother anybody, so likely being a sore loser doesn't really matter either. In New Hampshire, he has a larger lead, so his M.O. has been to not even spend much time there. He's flying around to other states and gambling his media presence is sufficient to carry the day. The strategy is that he is better not to subject himself to close questions, and the specifics of the plans, if elected.

So you think he has staying power?

He's going to be around for at least the next cycle. He has relied on his juggernaut brand to all but eliminate the necessity of advertising.

How would you explain to Canadians Trump's appeal to Americans?

I have a theory that it all boils down to his hair. His hair is like a clown's red nose. A clown gives you permission to laugh, even as he does mean things. Trump's hair is also a signal that you can laugh, and then listen to a kind of bullying or bigotry that ordinarily wouldn't be acceptable.

Trump is not unique in his views. He is tapping into things that other leaders have tapped into. He gets people to listen to things they wouldn't acknowledge they feel, and get to an aggrieved spot until it sticks. For example, what he says about Mexico and Mexicans. He is good at reading a market and giving people what they want to hear.

And the takeaway from the biography?

He's a cautionary tale of what the ingredients of success really are. They don't necessarily include the usual virtues we're all supposed to aspire to. Those are not necessarily helpful and sometimes a hindrance. He has a hyper awareness of what a situation really calls for, a good instinct for what's going to appeal to people and what they really want, rather than what they might say they want. 


This Q&A has been condensed and edited for clarity.