60 Summers Throwback: Interviewing Donald Trump in 1996

In the early 1990s, Donald Trump opened a helicopter service called Trump Air to ferry those who could afford it back and forth between Manhattan and the East Hampton Airport. The helicopters were smart and elegant, all black with the name TRUMP in big gold on the sides. In the second year of this venture he went through terrible business reversals and a number of his operations flirted with bankruptcy. There were problems with his Taj Mahal in Atlantic City. He seemed to be over his head with his ownership of the Plaza in Manhattan.

During that time, I interviewed him at his office in Manhattan for Dan’s Papers. What was it like to be so close to bankruptcy? He didn’t even want to talk about it. In fact, it seemed he didn’t even want to think about it. Instead, he talked about how everything he built would come back stronger than ever. And he talked about how years earlier he had rebuilt the Wollman ice skating rink in Manhattan for the City of New York, where no other developer even had a plan. He’d arranged for all the underwater tubing to be brought in and installed during one night, he said. He knew exactly what he was doing, and it was just full steam ahead.

I found him bombastic, opinionated, a braggart and full of himself. He was someone who took risks and shot from the hip. But he certainly was someone to be reckoned with. He ended the interview by inviting me to Mar-a-Lago for the weekend, and I took him up on it. The following year he sold the Plaza, got himself out of the Taj Mahal fiasco and shut down the helicopter operation. But that was so yesterday. He had bigger mountains to climb.

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