How an Old-School Gossip Columnist Explains Donald Trump

In the 1990s, A.J. Benza learned first hand how the real-estate developer got his name––and his net worth––in all the New York City papers.

Mike Segar / Reuters

Earlier this month, I heard A.J. Benza, the host of the celebrity-scandal show “Case Closed with A.J. Benza,” tell the podcast host Adam Carolla about his younger days as a gossip reporter in New York City. He hung out with celebrities until the wee hours of the morning, reported out sensational rumors, and constantly traded favors in order to get juicy tidbits for columns at Newsday and the New York Daily News. Most trades involved information he wanted about a particular person at a particular moment––and he would then owe his source a favor in the future.

“Donald Trump was the biggest guy in the world with that,” he said. “Trump spent every morning on the phone with me, with Page 6––he loved to get his name in the paper. As a result, he would drop dimes on other people in every industry he knew dirt on. You put the story in the paper, and then, three days later, you say, ‘Donald Trump was at a Knicks game with this supermodel.’ And he’s happy. That’s all it took.”

Calling Trump “shameless and shrewd at the same time,” Benza said “you might not like his style, but no one has played the American public and the U.S. government to this extent, and the media,” adding, “when he was with Marla Maples and we were going to write that they broke up, he cared more about ‘get my wealth in there, get the number right, how many billions I’m worth––that’s more important.’”

Hoping to learn more about Trump in those days, and what it is that makes him so much more successful than other publicity hounds at strategically generating press coverage, I wrote Benza, who agreed to an interview by email. In addition to his television gig, his memoir, 74 and Sunny, was published in 2015, and he’s the executive producer on the upcoming adaptation of “So B. It.” which debuts at this year’s L.A. Film Festival. Here’s a lightly edited version of our conversation.

Conor Friedersdorf: How did you get into the gossip-item business?

A.J. Benza: I had been writing sports for Long Island Newsday for a few years. After my divorce in 1991, I started heading into Manhattan and hitting any nightclub that would let me in. Once I made friends with a few doormen I was able to go almost anywhere. One night, I was pissed off at a curb because I couldn't get into Vogue magazine's 100th birthday party. Mickey Rourke took pity on me, threw me into his Lincoln and took me to a little spot downtown called Rex.

Within two hours every supermodel you've ever seen walked into Rex and plopped right down next to Mickey … and me. What I saw that night … drugs, sex, etc., blew me away. I called Linda Stasi, who was editing the “Inside New York” gossip page for NY Newsday, and gave her a few tidbits. Soon she got me hired at NY Newsday running around to parties for her. A few months later, Mort Zuckerman bought the Daily News and wanted Linda. Linda brought me along. Suddenly I had a good salary, a big office, and an invitation to get past any rope I wanted. A year later Linda wanted out of gossip, so Mort let me write and edit the page, “Hot Copy.” Eventually I added “Downtown,” a Sunday column all about me and my exploits.

Friedersdorf: It’s hard for people who grew up on TMZ and Twitter to conceive of what that corner of the media world was like back then. How did celebrity gossip work?

Benza: Nothing felt as good as when I was able to take a pebble of a rumor, report it out, and source it, then check and re-check it nine ways to Sunday. But the reality is, the gossip game was largely played on the barter system. To fill a blank page everyday for a city as high strung as New York, you can become somewhat dependent on publicists and managers and agents calling you and dropping a dime on someone so long as you were able to squeeze something in the column that helped them.

Having a PR flack sell out an A-List client's extra-marital affair wasn’t odd at all, so long as I was able or willing to get one of their smaller, but vital, clients in the column. And God help them if I had a bit of dirt on one of their clients. Then the real negotiations began: “What are you gonna give me so that I bury this story and no one ever sees it?” Unlike TMZ or Radar and much of the celebrity magazines, we never paid a single dime for any information. It was forbidden. But the column really came to light whenever a top celebrity or politician or developer called me directly. If you play those calls correctly, you’ll have a pocketful of favors. But the biggest difference in gossip, then vs. now, is we were more hung up on getting things right. Not so much getting things first. Always trying to be first, especially nowadays with the speed of social media, can get a lot of people in trouble. More “writers” all chasing less interesting content usually amounts to a lot of crappy stories.

Friedersdorf: What was Donald Trump’s role or place in the New York City media of that era?

Benza: It’s weird to hear Donald say he “hates” writers and doesn’t trust the media, because I only remember the many, many days where he phoned us, to either deny or supply a story.  And that’s not a bad mark on him, either. Most moguls and developers––let’s face it, the guys who run the city––have a penchant for trying to control or manipulate the press. I guess the aggravation he’s having now is see how much different it is trying to control ALL the columns, ink and electronic, rather than the wood, Page 2 or 3 and the more-pliable gossip columns.

But in the late ’80s and ’90s, it was impossible NOT to write about Donald. He was everywhere. And he was doing everything. He was getting divorced from Ivana, marrying Marla, becoming a dad again, fixing up Wollman’s Rink, renovating 40 Wall Street or Trump Place. It got to a point, wherever I felt I HAD to be for the good of the column, I’d run into him. SpyBar—check, a quick bite at Bowery Bar—check. Knick's playoff games—check. Front row at Victoria Secret's fashion show—check. So I’d write the column and not including him felt like I wasn’t doing my job. From East Hampton to Manhattan to Miami, he made sure he was always around.

Friedersdorf: When did you first interact with him?

Benza: I was subbing for Linda at “Inside New York” and The Donald (as we referred to him) called in. I was a bit nervous hearing his booming voice across the phone and he immediately disarmed me by saying (lying?), “Linda told me all about you. She says you’re a winner, and if your first newspaper job is working alongside her, then you must be.”

Just as I was being gracious, the other line was ringing. “Mr. Trump, can I put you on hold for a few seconds?” Trump shot back, “I can wait 10 seconds, how’s that?” The other caller was Mayor David Dinkins. When I returned to tell Trump I had to take the Mayor’s call, he found an opening. “Giuliani’s gonna beat him. Dinkins lost the Jews. The Crown Height riot is really gonna hurt him,” he said. “And you can quote me if you like.”

I never used his quote that day, but I knew I had someone who I could go to for any reason on future stories. And for years after that, Donald was a guy who lived and died in the columns.

Friedersdorf: Was there anything that distinguished the way he operated?

Benza: I once said, he doesn’t check his pulse in the morning––he checks the papers to see if he’s alive. And that’s not a knock on him. Keeping your name in print in NYC has value. But to say he was the only power broker to ring me would be a flat-out lie. A gossip column is only as good as its connections’ connections. I’ve often said all columns should have a list of all the contributors who helped break, shape, and slant every story that began with a rumor or a tip. If that were the case, Trump would have a prominent position at the tippy top. But he wouldn’t be alone. More people than you think used to call me and just chat away over a cup of coffee.

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.

Everyone is less discerning. Even reputable news sites are relentlessly covering things he says because they’re desperate to undress him. And in doing so, they undress themselves.

But only he feels fine being naked.

Friedersdorf: Whatever happens next, Donald Trump has shown the world a new way to interact with the media while winning a presidential primary. Is this an approach only he could pull off, by virtue of his unusual celebrity, biography, or personality? Or are aspects of what he’s done that future politicians will exploit?

Benza: I don’t see many politicians adopting his skill acquiring media coverage.

You can say he possesses “unusual” celebrity, but the adjective isn’t necessary. It’s celebrity, period. But at its core, celebrity isn't enough. Timing is also important, especially in politics.

Never before has the political world resembled a circus.

All Trump has done is put a face on The Strongman. And with everyone talking and gawking at The Strongman (or the anomaly), the circus gets a ton of attention, sells out every town, and rolls on without a hitch. I can’t see any other pol pulling this off or trying to adopt or whip up comparable anger. I don’t see anyone else with the same ego. And that’s saying a lot since everyone else who’s ever run for president have huge egos. But his is the size of Everest. There are experienced sherpas who wouldn’t dare climb Trump’s ego. But seriously, do you see anyone else channeling people’s id the way he has? He and Hillary can't be more opposite in the noise they make. She’s Crosby, Stills & Nash and he’s Twisted Sister. The country is screaming “We're not gonna take it,” not “Our House.”