It all started at the Phil Donahue Show in December l988. There I was, in the green room, interviewing Donahue for a Family Circle magazine profile.Donahue

And one of the guests on his show that day was the 42-year-old mogul Donald Trump, then rapidly expanding his empire with casinos, hotels, an airline, you name it.

Interviewer Me

I spotted the blonde-haired king of glittering high-rises standing alone in the wings, open and interested as I approached him, no handlers in the way. I told Trump that I’d just been hired by the New York Daily News to write Sunday magazine cover profiles. “And YOU’RE my first choice!”

“Call me,” he answered briskly. And what followed was a four-year adventure in Trump Land: The first was a story called THE PEOPLE’S BILLIONAIRE.Trump MagTrumpPlaskin2

But that interview was just the warm-up.

The following year, over a period of six weeks, we spent 11 hours together, for the Playboy Interview, one of the few times in the magazine’s history that they put a man on the cover.TrumpPlayboytrumplayboytext

I probed about his roots and life story, about his ideas about business and politics, and the result hit the front pages of the New York Tabloids.

To this day, the Trump Playboy Interview hangs on the Republican Presidential nominee’s  office wall, framed in gold, as many things are in Trump Tower. And even now, as he’s running for President, the viewpoints he expressed in our interview long ago are still relevant, this according to The New York Times, which recently called the interview ‘prophetic.’ During the Republican Convention, National Public Radio also fleshed out the Playboy Interview and Trump’s relationship with the media. And if you want to listen to the RADIO INTERVIEW version of it, it includes my viewpoint and other commentators, some of whom are drearily negative.

From my original introduction:

“At Trump Tower, after being visually frisked by a troop of basketball-player-tall bodyguards, I entered the inner sanctum. There was Donald Trump, as he would be for most of our sessions, slumped behind the cinnamon-colored desk, slung comically low in his chair…‘I think best this way,’ he’d deadpan.

“Supervising his office like an exceedingly well-run vaudeville show, executive assistant Norma Foerderer would wander in with another gold-framed magazine cover to put up on his wall–or with a seven-pound cheese-cake or a stuffed skunk. Trump would take calls during our interview–never for more than a few minutes–that invariably ended with, ‘OK, baby, you’re the greatest.’ Then secretary Rhona Graff would walk in, bearing little yellow slips of paper announcing calls waiting: down-on-his-luck financier Adnan Khashoggi, asking to have lunch; a hotel executive, dickering to sell yet another big hotel…. By the time Duchess Fergie called about borrowing his brand-new accident-proof helicopter, and Don Johnson to borrow his city-size yacht, I was dizzy.Helicopter

“We began our first session hovering above the East River in the cobalt Darth Vader helicopter. Donald Trump was strapped into taupe leather, good-naturedly hyping his empire below.”

After this interview was published, I continued my Trump rounds and did two more interviews that were intriguing exclusives,  subsequent covers stories with his first wife, Ivana, and his second, Marla–this a print interview given only to me during the height of the tabloid circus that followed Trump as he ended one relationship to begin another. Ivana was, without doubt, the most stunningly-groomed woman I’d ever seen in person, an executive at the Plaza Hotel with impeccable standards. When I later met Marla, she was exquisite looking, beauty-pageant lovely, and ever so young and idealistic. She was the most mature 24-year-old I’d ever met. That’s for sure. 
IvanaMarla Cover2

Later, when my Turning Point book was published, Marla flew to Chicago with me to appear on Oprah.

None of this would have happened had Donald Trump not allowed himself to be closely questioned.


As in interviews today, this mercurial, controversial figure is leading with his gut, just as he always has, following his intuitions and instincts. And while he  often expresses intense disdain for media reporters, he certainly remains the master of the game.