You’d be surprised how many great, big stories were born during those conversations. Trump’s honesty (yes, I said it) was always refreshing. And a lot of people are seeing that today. He says things many of us feel. Sure, he puts his foot in his mouth sometimes. He’s less apt to admit that, but he’ll easily mention, with that high-stakes poker face of his, that the custom shoe on that foot is worth $1,400.
And by saying that, you come to see that he’s a ball-breaker.
Friedersdorf: Do you have any Trump stories that have been forgotten or never heard?
Benza: It wasn’t too long ago that we’d be talking about sports or business or all the pretty, city girls that I’d hang up and think, “Wow. The guy’s a billionaire and we have so much in common.” That commonality came back to haunt me a few years later, when we were both vying for the heart of a very beautiful woman. And our dating her might have overlapped a bit. [Trump and Benza once fought over this on the Howard Stern show, with Trump claiming, “A.J., I won your girlfriend.”] But what stands out some 15 years later, as I still count her as my greatest friend, is how he went about it.
This is a guy who is one of our generation’s best closers. And just because he’s a billionaire with a golden toilet (I’m guessing), doesn’t mean he goes about everything as a crass, emotionless power player. What much of America hasn’t seen yet is the silly, compassionate, charming side to the guy. After the three of us all moved on to new spouses and had children, I would ask her “what is it I’m not seeing with this guy?”
She didn't give me the type of stories I’d imagined—private planes, an endless bank account, villas all over the world, etc. What stood out for her were silly moments or sweet gestures. She told me about the time he took her backstage in Atlantic City to see James Brown and how he put on a cape and danced with the man, or the fact that her mother is still alive today because of the top-notch medical care he organized and went into his pocket for. Or the time he had a stretch limo pull up to her West Village apartment so that she and her little boy could go to the Natural History Museum. And how startled she was when, exiting the car, she turned to thank the black-cap wearing, mustachioed driver, only to see it was The Donald in disguise.
Friedersdorf: Why do you think Trump has been so successful at gaming today’s media ecosystem?
Benza: The media ecosystem is ripe for takeover. The loudest, most popular voice usually wins. It’s no different than the atmosphere in a high-school cafeteria.
Give the crowd something to actualize their anger on and they’re off!
And I don’t find fault in him standing up and shouting. He’s right, a lot. The system’s shit and the food sucks. And he’s no more exact than Howard Beale, but yet he’s too often right on the nose. In general, people like getting angry––they’ll worry about the reason why later on. And with the expansion of social media, the outlets of coverage are a lot less choosy. The writers are less savvy and even less objective and the myriad of websites and column inches are more likely to cover the noise.