Very Trumpy Post

A breakdown of the three times that I photographed Donald Trump.

In 2004

In 2004, at the height of “The Apprentice," I was called to shoot him for Newsweek. I was specifically asked to get pictures of him making the “You’re fired!" gesture. No one looks good doing that face, but it was iconic at the time.

We did shoot a few other setups, including one weird one where I had him holding an example of a wall sconce. I suppose this was the “extra shot for me." 

Early in the session, I had him sitting in the middle of the conference table, and looking to break the ice a bit, I mentioned that I had photographed his daughter, Ivanka, the year before. I told him that she was low-key and polite and seemed like a decent person. And then I went the extra step, saying, “It says a lot about the character of a parent when a child exhibits such decency and poise.” Amazingly, it worked, and after that point, he relaxed a little and became more cooperative.

My friend and fellow photographer Kyoko Hamada had photographed Trump, so I asked her what her experience was like. She told me that he kept saying, “I have many important people waiting for me." We had a good laugh about it because it was insulting to the person he was saying it to. Like, these other folks are important, but you’re not.

This turned out to be helpful, as halfway through our session, he said this exact thing to me. Knowing that he says this to every photographer, I just ignored it and kept shooting.

In 2006

Two years later, I was sent back to photograph him in the same Trump Tower conference room. Knowing the space beforehand helped me plan a shot list.

This shoot was for Philadelphia Magazine. They had a “Trump is Everywhere" theme as he was making some big real estate moves in the city of brotherly love.

Inspired by the magazine's concept, I brought along some friends dressed in business suits and had them hold Donald Trump masks in front of their faces. Having a crowd of people, even a small one, changed the dynamic, as now Trump had an audience. He was the most lively and playful on this shoot.

For the first setup, I had my extras in the elevator with Mr. Trump by the door. As I shot, I was moving closer and further from the group, and Donald asked me, “Hey, is that a normal lens or a wide lens?“ “Oh, it’s a wide lens.“ He jumped right in, “It will look much better with a normal lens, don’t you think?“ “Mr. Trump, are you telling me how to do my job?“ The group of extras in business suites were myself and my wife’s friends, so they were delighted to see me spar with this international public figure. After a beat, Trump added, “Oh, no no.” Both of us got hardy laughs from our audience.

The next setup was with the same group lined up in the conference room. With Trump upfront, looking strong and stern, and a sea of business figures holding Trump faces around and behind him. I said to him, “You’ll like this one, Mr. Trump, it’s shot with a normal lens.” He leaned in, pointing and said defiantly, “This is the one that they’ll use!” And of course, it was.

That setup ended on a high note, so I pulled out an 11x14 white envelope, with a hint of theatricality. He asked, “What is this?” “It’s a little gift, to buy an extra setup.” And I slipped out the picture of him with the wall sconces from the previous session. He looked at it approvingly and said, “Sure.”

This is how I got the iconic portrait of Trump with the mirror slats. Shot on a tripod with a slow shutter speed, using the window light streaming across the large conference room.

It was eerie and beautiful, but when I made it, I thought of it as being a cool, weird picture of a well-known figure. I had neither a high nor low estimation of Donald Trump; he was just another businessman TV personality to me.

This one fits within my practice of trying to make an interesting picture for myself on every shoot. In fact, at the time, I thought it had been more about me, fractured and broken, than anything to do with the story of Trump himself.

Also, at some point, I realized that a handful of my pictures would be meaningful in the long-term, and it wouldn’t necessarily be the obvious ones. It’s high stakes when I’m photographing someone already important or famous, but I’ve learned that making interesting pictures of people before their notoriety is the most impressive. It feels like I’m predicting in the future; like I’m clairvoyant, knowing that this person will be important later.

I don’t have that sensitivity, and oftentimes the people I find the most intriguing or talented don’t become widely known or remain important. I just try to apply some level of seriousness to every shoot, on the off chance that this will be the one that blows up.

In 2015

Nine years later, I was called to photograph Trump again, and he was running for president. It was for the Wall Street Journal, and we shot at Trump Tower, but this time we had access to his private quarters. We first shot in their campaign space in the basement, and then in his apartment up in the tower.

At the time, I thought, “Why is this schmuck wasting everyone’s time with a presidential run?” It shows you what I know! I have a consistent record for not predicting the next president. I thought the same thing when meeting with George W. Bush in 1999!

We shot a few different setups, all of which ended up being pretty uninteresting. The combination of his gold-plated apartment, lots of picture windows, and a more controlled subject led to a lot of nothingness.

Ironically, the highlight of the visit came when I showed him my mock-up for the Uneasy book. I turned to his 2006 mirror portrait, and he was pleased. But then he paused and pointed to the laptop showing the new session, and said, “The one in the book is great, but this one is better.“ He did not specify why he preferred it, but I couldn’t help but think that he liked the picture with more gold in it.

My assistant shot stills and video of us with the maquette, including Trump offering me a blurb for the back of the book. “How about, ‘Great photographer, great book!'" Sure, I’ll take it!

***

My political take on Donald Trump is complicated. I do follow politics, but through the lens of entertainment and distraction. I have my opinion on specific politicians and issues, but I’m not passionate about it and certainly do not voice my take publicly.

I usually assess people on how they treat me, and how my experience with them is. I vote for candidates based on policy positions, but I speak well of folks who treat me decently and deliver great photographs.

And Trump is less obnoxious in person. Yes, he can be dismissive and disrespectful to photographers sometimes, but the guy likes having his picture taken and understands what makes for a dynamic image better than most public figures.

It strikes me as a little sad that I’m only posting this content here, and not in a more trafficked space, like Instagram, but some people have a hard time dealing with politically oriented content without getting angry or emotional. You’ve made it this far, so enjoy.

Top Image: Philadelphia Magazine opening spread, May 2006. Designer Keith Webb.

Second Image: Outtake from the Newsweek session, February 17, 2004.

Third Image: Left: With the wall sconce. Right: The wide-angle elevator scenario.

Four Image: Rejecting the small American flag on the Wall Street Journal shoot, September 10, 2015. (See the video of the scene, here)

Bottom Image: Behind the scenes, 2015. Photo by Michelle Watt.