The last time I saw Donald Trump, he was screaming at me on stage at the Hollywood Bowl.
In 2006, I was a contestant on Season 6 of The Apprentice, the NBC show in which 18 contestants competed for a managerial job working for Donald Trump, the program’s host. Each week, members of the losing team would be called to Trump’s boardroom where at least one would be “fired.” I lasted eight episodes.
At the season finale, those of us cast off in earlier episodes were brought back to witness the spectacle of the winning “apprentice” being chosen before an audience, in a live broadcast. Sitting onstage in a fake boardroom set, Trump asked the former contestants for their opinions on which finalist he should hire, turning finally to me before announcing his decision. I jokingly suggested that he choose Sanjaya, the goofily flamboyant singer then enjoying a run on American Idol. I meant it as a quip about the triviality of the whole self-serious reality-audition process. It was live TV, so I couldn’t be edited out.
Moments after we went off-air, with the stage full and audience members still exiting their seats, Trump spotted me and jabbed a finger at my face. “What was that?,” he barked. I told him the truth: I had nothing nice to say about either of the finalists, and rather than insult them, I went for humor. Humor was not, apparently, welcome in the boardroom.
“Well, it wasn’t funny,” Trump snapped, his face inches away from mine. He stormed off.
Up to that point, I felt I had been on Trump’s good side. It’s true that he’d fired me, but he fires most people on the show, and some of them have gone on to be his biggest boosters. Somewhere in my parents’ house, there’s even a personal post-firing letter from Trump, encouraging and complimentary. So naturally, I was taken aback when my joke turned into an onstage browbeating.
As Trump closes in on the Republican nomination, I’m constantly asked about the man and his campaign. I even wrote a book on the topic, Decoding the Donald. Since last summer, I’ve watched Trump mount his incendiary campaign for the presidency — full of quixotic promises, bombastic rhetoric and petulant personal attacks — and memories of my time in Trump’s TV universe resurface.
The premise of his show was more or less the pitch he’s making to America: Trump is the boss, and he’ll hire the best people. We were supposedly competing to be mini-entrepreneurs, team leaders, junior managers executing their ideas in a business empire. This wasn’t quite what the show rewarded, though. What it largely rewarded was giving attention to Donald Trump.
Off-camera and during interactions with him on our “rewards” for winning tasks, Trump was jovial and soaked up attention. In the boardroom, Trump was dominant and responded best to sycophantic praise or other overtures to his ego. Giving him good ideas could have some payoff in the competition. Pandering to Trump, however, was far more valuable.
This isn’t to say Trump wasn’t charming. Just as he effectively uses humor at his rallies, Trump regaled us with jokes — kidding us about the budding romance between contestants, or unexpectedly dropping a “fo’ shizzle” when announcing that our reward one week was to rap with Snoop Dogg. Maybe it was just the charm of a rascal who just doesn’t operate with a filter. Maybe it was all an act. Either way, Trump had a charisma that could balance out his crass tendency to say or do things that other people’s conscience or sense of decency would never allow.
The most memorable moments, revealing the aspects of his personality I’d never forget, usually happened off-camera. In the second episode of my season on The Apprentice, my team won the week’s competition, and as a reward, Trump escorted us on a trip to the Playboy mansion, where we would party with Hugh Hefner and whatever Playmates were there. My team consisted mostly of women. As a chauffeur opened the door on our limousine, we were greeted by Hefner’s three then-“girlfriends,” Kendra Wilkinson, Holly Madison and Bridget Marquardt, who were then costars on a reality show of their own. They ushered us inside. After a fireside chat with Hef, we headed to the backyard, where dozens of women — some wearing bikinis, others sporting bunny ears and bowties — surprised our team with a pool party.
Toward the end of the evening, I found myself in a small circle, conversing with Trump, Hefner and another contestant. With a wry smile, Trump looked at Hefner and said, “It’s hard for me to tell which of these girls are yours, and which ones are mine.” The women on my team were well-credentialed business executives, people Trump had supposedly hand-picked for their skills. In that moment, the only real difference to Trump between them and the scantily clad Playmates who were there for his entertainment was that some of the women were “his,” and some weren’t.
Life on The Apprentice was a carefully orchestrated performance. During the casting process — before filming even began — I was carefully coached by the show’s staff to talk up how much I respected Trump, how much I could learn from him, and why appearing on the show would change my life.
Once the show got underway, that kind of obsequious personal pitching became regular groveling for Mr. Trump’s approval. And yes, every contestant was explicitly instructed to refer to him only as “Mr. Trump”—a tic his staff enforces today on the campaign trail. Since he ostensibly decided which of us to fire, we didn’t have much of a choice: We were deferential and solicitous; time and again, I was prompted to repeat the fawning platitudes that had gotten me on the show. Cameras followed my every move while producers whispered in my ear, keeping me wrapped up in this distorted reality.
By now, most viewers know that the “reality” on each reality TV show is a carefully created bubble of its own, and I came to think of the reality on this show as Trumpland. In Trumpland, the rule of Mr. Trump is absolute. In Trumpland, you have human worth only if you please The Donald. In Trumpland, female business executives are no different than scantily clad Playmates, or at least have to keep quiet if they’re placed in the same box. In Trumpland, a step outside the lines drawn by Mr. Trump, like my joke about Sanjaya, triggers a sharp, furious response.
After a while, living in Trumpland yielded exactly the result that the show’s producers wanted: a low-stakes Stockholm syndrome. I actually did want to win as the show went on. I became the person I had been trained to be, and took the entire absurd “job interview” process seriously. When I was fired, I felt disappointed and empty. I had dedicated every waking minute to competing for Trump’s approval, and had just been given the exact opposite.
Today, when I watch the rallies and the friendly TV appearances, I get the distinct sense that the line between Trumpland and actual reality is blurring. Donald Trump has turned the campaign into a reality show, and we can’t seem to stop watching. Having lived in the former, I can attest that’s not a good thing.
The Donald Trump I saw up close is very much the same man who alternately captivates and revolts America. As a candidate, he’s been uniquely attuned to poll numbers, turning them into a talking point in a way no candidate had imagined before. Past Apprentice producers and contestants have described his obsession with the show’s ratings. When an episode lost the prime-time ratings war to American Idol, it was enough to make Trump “totally downcast and dejected,” according to one former associate.
On the trail, even if he can’t get the rest of the world to call him “Mr. Trump,” his deep personal insecurities have given him a real political advantage: He knows how to capitalize on others’ insecurities.
Want to throw off an opponent? Do something out of bounds, like attacking their spouse’s appearance. Want to embarrass a boyish 22-year-old Apprentice candidate who lacks your machismo? Sit in your boardroom, cameras rolling, and ask him if he’s a virgin. Want to win white working-class voters in the midst of an existential crisis? Attack immigrants, advocate a border wall, and promise to bring those would-be supporters back to a simpler time of cultural and economic supremacy.
Comparisons between elections and reality TV aren’t new, but I definitely found myself tracking the primaries the way a casting team would think about an Apprentice season, and it was surprising how well it tracked the arc of a reality show. Starting with more than a dozen competitors, the Republican field was remarkable for its sizable and quirky cast of characters. The country’s most famous reality TV persona then theatrically dispatched his primary opponents one-by-one. Jeb Bush was the geeky teacher’s pet, Marco Rubio the popular athlete. Ted Cruz, the know-it-all plotter, is still in the game, as is John Kasich, the regular guy.
For Trump to reach this stage in the campaign required his Ph.D. in reality TV.
Trump formed an early alliance with Cruz, the wiliest opponent; he quickly neutered the early favorite, and he strategically ignored lesser contenders. He kept up the likable rascal front — Don’t like me? That’s your problem, not mine — but like many reality TV stars before him, Donald Trump did not come here to make friends with the rest of the cast members. He came to engineer their downfalls.
I did eventually emerge from my Stockholm syndrome, although it took a while. After my final “conversation” with Trump onstage at the Hollywood Bowl, and with time to digest the whole experience, it came to seem more and more absurd that I’d seriously competed for his approval. Today, with my time in Trumpland long behind me, I find myself questioning why I had ever wanted it in the first place. I can’t help but wonder if the supporters at his rallies will eventually find themselves asking a similar question.
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