What Making Deals with Donald Trump and Jared Kushner Taught Me About Deception

About 13 years ago, I walked into Donald Trump’s office hoping to sell him advertising in The New York Observer. At that time, I was publishing director of the newspaper, which was still owned by my father, Arthur Carter, but I could see a potential sale of the struggling paper looming and sought to fend it off. In those days, I sold ads because I had the noble idea that I could save the newspaper. That didn’t happen. But over time, I did grasp something about the nature of selling and witnessed a range of ways in which it’s achieved.

That day, Trump — who was speaking on the phone, to one of his children, I believe — smiled, greeted me wordlessly and pointed to a chair. He had no intention of pausing his activities because I had arrived for a meeting. He continued on in a seemingly friendly, inclusive manner, but ignored the stated purpose of my visit. He picked up the phone intermittently, while employees wandered in and out of the office. A consummate performer, he appeared to be conscious of his audience. I tried to corral his attention and began my sales pitch several times, but I don’t think I spoke two uninterrupted sentences. He chatted with me off and on, talking fondly of his kids, then asked my advice on interior design for one of his properties. It was a question about gilded molding, I believe.

“You like this one?”

“Yes.”

And then, my allotted time was up.

On my way out, Trump beamed at me. “You’re so thin!” he cried out. I didn’t have a good response to his oddly inappropriate comment, which he probably intended as flattery. I smiled awkwardly and waved goodbye. Unfortunately, he didn’t buy ads from me that day or any other day. I doubt he ever intended to. He probably met with me hoping to ingratiate himself and get some positive coverage from the Observer.

A year or two later, in 2006, I was seated with my father in his living room and 25-year-old Kushner walked in. This time, we were selling the whole newspaper. I don’t mean to inflate my role — I was merely on the selling team, just a passive spectator. Nevertheless, I had a personal stake in the outcome, having gone to work for my father with the idea that I’d take over when he retired. I experienced the sale of the paper as a crushing blow. I’d moved to New York to work there and invested five years of my life. But if it was inevitable, then at least I could hope for a like-minded owner, ideally someone who’d welcome my presence and assistance.

Kushner positioned himself as a naïve protégé who looked up to my father as a mentor. His family’s name had recently been sullied by his own father’s misdeeds and subsequent time in prison. He had yet to meet Ivanka Trump. In retrospect, it seems clear to me that his desire to acquire the newspaper had to do with rehabilitating his family’s image. The Huffington Post reported that a family friend of the Kushners said the move was one of three suggestions public relations guru Howard Rubenstein gave Jared. (Kushner Companies and Rubenstein denied the account.)

Outwardly modest and guileless, eyes and chin down, he talked in his soft-spoken voice of his respect and admiration for this venerable institution. He said if he were to own the newspaper, he would be eager for my father’s continued participation as well as mine — in fact, he seemed enthusiastic about my staying on at the Observer. Lastly, he implied he had enough money to keep the paper running forever.

Kushner was effective in selling himself to my father and me, but I would grow to realize that his interest in the Observer had nothing to with a love of journalism, or even a passing interest in journalism. Once he owned the paper, colleagues told me he said he found it excruciating to read — and acknowledged as much in a 2009 New York magazine interview. Once he owned the paper, we barely spoke. Kushner didn’t fire me, nor did he formally demote me. But I left after six months, when he’d made it clear to me, with his lack of words or a blink in my direction, that he did not intend to work with me.

Almost everyone has to sell, no matter your occupation. It’s one of the hardest and most underestimated jobs. Though I didn’t excel at it, I recognize what it requires: sharp intuition — the ability to discover who people are. Salespeople are social creatures who enjoy learning. They figure out people in order to provide them with what they want or need. At least the principled ones do.

But there are other sorts of salespeople who take the exact opposite tactic — you might call them show people. They are the ones who go through life projecting an image ceaselessly. They believe success comes from the ability to ignore information that doesn’t suit them. They write their own narrative, and they commit wholly, relentlessly.

Every president this country has ever had was to some degree a salesman. But it is clear to anyone who has done business with President Trump that he views the presidency as an extension of sales: in his view, it is an occupation that has little to do with listening. To take in new information, he would need to stop projecting an image.

You could have seen this at the listening session held at the White House on Feb. 26, in which the President spoke with governors about school shootings. Twenty-five seconds into remarks from Washington Governor Jay Inslee, the President crosses his arms; when Inslee stopped speaking, Trump quickly refuted what the governor said and moved on to someone who agreed with him.

Kushner, too, never stops projecting an image. Though Senior Advisor to the President and Trump’s son-in-law, the public has little first-hand knowledge of his character. Witness this recent and somewhat puzzling story on BuzzFeed, which emphasizes his opportunistic streak: “Kushner Sought To Sell Newspaper to Trump’s Political Enemies” shortly after the 2016 election.

Perhaps wishful thinking led me to believe in Kushner’s initial sincerity when he bought the Observer because it served me to do so, but eventually I felt duped. Once he owned the newspaper, his deferential attitude was replaced by a posture of superiority. That air of superiority, as opposed to authority, defied common sense because he had no experience in journalism. At times, it seemed to me that he was acting a role and knew he was. At other times, it seemed more likely that Kushner had come to believe his own performance. Given his prominent role today, either is a disturbing prospect. Apparently similar to President Trump, he didn’t and doesn’t know that leadership has to do with learning and listening. For this White House, leadership is about presentation. All you need to do is say it, and then it will be true.

Carter’s work has appeared in The Economist, The San Francisco Chronicle, The Chicago Tribune, The Philadelphia Inquirer, The New York Observer and other publications.