Photographing a Future President

Photograph of a man throwing an apple against a blue sky background
Donald Trump / Michael O'Brien / 1989 / National Portrait Gallery, Smithsonian Institution / Gift of Sally and Bill Wittliff / © Michael O'Brien

I was assigned to photograph Donald Trump for Fortune magazine in 1989. Fortune was doing a story on billionaires. Obviously, no one knew then what his future held!

As soon as I got the assignment, I visualized the image: Trump against a Magritte sky, looking confident and back on top. Trump had just come through a rough period in his business, but was bouncing back.

On the day of the shoot, I realized the photo needed an accent—something unexpected, but revealing. Bingo! A big red apple popped into my head. I was living in Brooklyn at the time and stopped off at the neighborhood fruit stand. I bought a couple of great candidates before the drive into Manhattan.

I began by photographing Trump without the apple; you never know how cooperative the subject will be. I got the “safe shots” of Trump solo against the backdrop. Next, I brought up the idea of him tossing the apple. He got it immediately. ”Great idea!” he said.

The shoot went perfectly. Trump was more than cooperative. This was before the age of digital retouch. I had to capture the moment perfectly on film. A surreal sky with a red apple floating magically at its arc. He tossed the apple again and again and again. His only complaint was that his arm was getting tired.

I knew I had made an excellent picture. The photograph was published in the September 11, 1989, issue of Fortune. The editors ran it a few sizes larger than a postage stamp. I was miffed. A good shot had gone to waste. This issue, like most newspapers and magazines, went out with the kitty litter a couple of weeks later—gone and forgotten.

A year later, an editor at Random House saw the photo and seized on it for the cover of Trump’s autobiography Trump: Surviving at the Top. I felt a little better. The picture had gotten a second life; the image had grown a little larger.

The original image then sat dormant in my files for more than twenty years.

Between 2009 and 2011, the Smithsonian’s National Portrait Gallery accepted a selection of my portraits as gifts from NPG Commissioner Bill Wittliff and his wife Sally. I gathered my favorite photographs: Willie Nelson, LeBron James, Don DeLillo, Howard Finster, Larry McMurtry, Warren Buffett, and others. I was nearly finished rounding up the images when I remembered the ’89 photograph of Donald Trump. Why not, I thought?

The National Portrait Gallery acquired the Trump photograph along with sixteen of my other portraits. The Trump portrait went on display in the museum in January 2017. It’s the third life for the image, which has become ironic. Who knew all those years ago that Trump would become the U.S. president?

They say a cat has nine lives… Well, this photograph has had at least three lives to date.

-Michael O'Brien