I Interviewed Donald Trump and It Just Made Me Feel Sorry for Him

Success, and its gaudy trappings, is all he knows to fill the yawning chasm within.
Publish date:
December 15, 2016
success, Donald Trump

About nine years ago, I interviewed Donald Trump.

This was in another lifetime. This was before he became a living Simpsons joke/our tweeting president-elect, and before I had the courage to open the successful coaching practice I now run. That entire period would, in fact, have worked on many different levels as a provocative life lesson about the devastating effects of poor choices and fear, if the main lesson wasn’t also, you know, my life.

The production company I worked for was fifth-rate on a good day. On a bad day, it was like the closing credits of the Benny Hill Show. You commit to your fears, and your fears really come through in a big way, n’est-ce pas? The production company worked with a lot of celebs, some big, most small; one day, as the staff producer, I received the assignment of interviewing noted entrepreneur Donald Trump.

As a native New Yorker who grew up snickering over Spy Magazine's gloriously mean-spirited commentary of all things "The Donald," I was too busy girding my loins to be thrilled. Meanwhile, my Russian cameraman, who had just delivered himself of a rousing declaration to stop, cold-turkey, his two-pack-a-day cigarette habit, in honor of his newborn son, upon hearing of our assignment, immediately made the executive decision to stop stop smoking and purchased a carton of something tarry and delicious from the local bodega.

This was years ago, so I have only the vaguest memory of the reason for our shoot. The Apprentice maybe? Considering how poorly managed the company was, I’m sure they still have the footage we shot, safely encased in one of their numerous, immaculately organized tape libraries. (Translation: lost, stolen, thrown out, behind the toilet, smashed into bits, erased, etc., because journalism. And competency.)

Silent and grim, my cameraman and I made our way to Trump Tower. We were shown into a small room, bright with glitzy views of Fifth Avenue, to set up our gear. As I prepared my questions, all too soon a feathery nimbus of yellow hair entered the room: Trump, with a few members of his entourage. I walked over to introduce myself, and as I opened my mouth, and held out my hand, Trump cut me off, pointing to a scrap of paper stuck on an extremely classy light switch, snarling, “What the hell is that? Did you put that there?”

Right about now I should alert you that previous to joining this company, I had worked in fairly high levels of network news in Russia, Washington, DC, and NYC. Therefore, spoiler alert: I’ve been berated by the best. TV news, to paraphrase the famous Soviet film, does not believe in tears. Alcoholism, rage, infidelity, bad makeup, temper tantrums, other people’s misery, stupidity, lies and poor grammar — why yes! Tears? Not so much. Reporters have thrown profanity, cocaine, chairs, coffee mugs, sandwiches, phones and, once in Moscow, a full water cooler at me. I have broken up fist fights between drunk colleagues. That anchor who tried to sucker-punch a pregnant producer. The time my tape editor went out for lunch and called me, hours later, asking to be bailed out of Rikers — the diner had ruined his cheeseburger.

All of that colorful backstory to explain that when Trump attempted to demonstrate to me that he was a bad hombre, I had to bite my tongue in order to avoid cackling. I've sat in daily planning meetings with pre-makeup Nancy Grace; your abyss better eat its Wheaties, son.

In the calming tone one uses with errant toddlers, warning them that not today, Satan, I replied, “No, of course not. We’ve been here setting up for your interview, Mr. Trump.” He immediately backed off, saying, “Oh. I knew that. You guys are great! It must have been one of the cleaning people. Nice to meet you!”

The red light went on, and we got to work.

From the moment Trump entered the presidential election, I kept thinking of that incident — of how Trump choose to begin a business encounter with bullying and domination. Even though we were in his lair, at his invitation, to profile him, Trump had to make sure that we knew who was boss.

Today, as I write this piece, I’m my own boss. I finally stopped making excuses, left that production company, and launched my own coaching practice. Starting my own business, allowed me to grow up and become the woman I needed to be. And that process, the grueling action and responsibility of creating something real from nothing, of committing to my hopes instead of my tedious fears, was yuge. It forced me to understand that success is a very amorphous condition. Success is relative. Success solves everything and nothing. Success can taste like failure — and vice versa. Success is something every man and women must define for themselves, a definition that is likely to change over time as they evolve and grow.

But for someone like Trump, SUCCESS is not everything, it’s the only thing. SUCCESS, and its gaudy trappings, is all he knows to fill the yawning chasm within. And that’s a killing lifestyle, a cannibalistic lifestyle to uphold, because SUCCESS is ultimately meaningless. It’s the authenticity of the lives we lead that matter.

Our interview with Trump was brief — no more than 10 minutes — and once we had what we needed, we stopped tape and thanked him for his time. Now, knowing that we were leaving and that we wouldn’t ask him any unpleasant or irritating questions, Trump became almost… well, perhaps charming is a stretch, but he seemed to relax. His smile took on a genuine(ish) inflection. If he had known how, he would probably have tried to make friends.

Shaking my hand, he burst into over-the-gold-ceiling-top praise of how wonderful I have been as an interviewer, assuring his eager factotums, "Isn't she wonderful? She’s so beautiful. She did a great job — much better than any anchor!"

It'd be easier for me to hate Trump if I didn't have such pity for him.