We all tried to make a positive impression on “task delivery” days, but it rarely happened. The only chance to have dialogue with Trump was in the boardroom. Everybody else was trying to stay out of the boardroom so they wouldn’t get fired. I gambled the other way and tried to get in the boardroom. If I could talk to him directly often enough, he would get to see me in action, see my value and appreciate my strengths. The other women repeatedly nominated me for the boardroom, which helped me get more face time with Donald J. Trump. It was a big risk that paid off.
While in the boardroom, I continued my Trump studies. I observed his nonverbal cues. For example, whenever there was a disagreement or an argument, his eyes lit up. He loved conflict, chaos, and confusion; he loved seeing people argue or fight. He sat up even taller when people made a strong case when defending themselves. I adapted my boardroom strategy accordingly. Sometimes I gave backhanded compliments to my fellow contestants—and Trump would zero in on it. If I was openly critical of them, he’d smile.
I had an advantage over the other contestants because I wasn’t easily intimidated by authority. Walking into the boardroom with Trump was a cakewalk compared to working with political powerhouses, law enforcement, cabinet secretaries, Congress members, and heads of state who came to the White House. I was conditioned to deal with the egos, the personalities, and the quirks of very strong, powerful people and not to be afraid of them. Powerful people like individuals who don’t seem overwhelmed or nervous around them. Trump demanded respect and deference, but if you showed fear, he couldn’t return that respect. My calmness helped me in the boardroom.
The boardroom tapings were brutal marathons. We spent hours in there with no bathroom or food breaks. It was like an interrogation. I specifically remember a contestant asking to use the bathroom once. She was told to “just hold it in.” We all learned to go to the bathroom before the boardroom and never to ask for a break in the middle of one.
Five hours is a long time. Everyone lagged, except for one person—Trump himself. His energy was high and his focus sharp. He engaged on an elevated level and had a full grasp of the rules and parameters of each task. He knew each of our names and performance histories, show by show. He spoke with a wide-ranging vocabulary, made eye contact, and sat still. He analyzed our performance and arguments on the fly. He kept all these balls in the air at the same time, without any sign of fatigue or stress. Trump seldom took food or bathroom breaks, either. He didn’t ramble or get confused. He bragged, of course, but his stories were relevant to the discussion at hand. The conversations were productive, and the man couldn’t have been more impressive. The Donald Trump of 2003 was as smart and shrewd as he claimed to be.
The task on episode four was to take over the dinner rush at Planet Hollywood. The woman on the team ran the bar and flirted with customers to entice them to order more drinks. The boardroom discussion focused on the profitability of women using their sexuality to sell. A sanitized version appeared on TV, but the outtakes and off-camera moments were not appropriate for a family show. Trump asked personal questions of the female contestants, like “What do you think she’s like in bed?” and “Do you think she’s sexy?” Then he turned to the male contestants and asked, “Who do you think would be better in bed between the two of them?” and “Rate how you think she’d be in bed.”
At the time, I didn’t think much of these exchanges. The conversation was about the marketability of sexuality, and he was asking about the potential of each candidate on that measure. I thought it was just part of TV production, Trump being provocative. Now I know better.
In episode six, the task was to enlist celebrities to do a charity auction at Sotheby’s. I was selected to be the project manager and our team lost the task. I was eager to go into the boardroom to make my case to Trump and the advisers. As the losing team manager, I got to choose who to bring into the boardroom with me, and I tapped Heidi Bressler and Jessie Conners. Donald asked me, “How did Heidi do?”
“Heidi was fantastic,” I said. “And I will tell you that I haven’t always been a fan of Heidi. I haven’t always thought she was professional, nor did she have much class or finesse.”
“That’s the worst compliment I’ve ever heard,” said Donald. To Heidi, he asked, “Do you think Omarosa has class?”
“You know, in the beginning, I didn’t think she had a lot of class,” said Heidi.
“You like her now?”
“I do like her.”
“You mean after that last statement, you like her?” Trump prodded. “If somebody said that about me, I wouldn’t like her. I don’t care what they do. And just now she—she knocks you and you’re saying how much you like her. There’s something wrong.”
Then he moved on to Jessie and asked her whether she liked me, despite the way I was talking to her. Like Heidi, Jessie said she “liked” me.
“How can you like her the way she’s talking to you?” Turning back to Heidi, he said, “She destroyed you with a compliment.” Back to Jessie: “She knocks you, and you say how much you like her . . . either you’re not telling the truth, or you’re not very bright.”
He was shocked that they didn’t defend themselves. Shrinking from conflict, in his eyes, was worse than a poor performance on the task. I’d insulted them, and Trump credited me with “a very sharp edge.” He fired Jessie.
His praise meant a lot to me. I started to feel like my efforts to show him my value and toughness were working. He seemed to be singling me out with questions, and compliments, and I reveled in it.
• • •
WE FINISHED TAPING in the beginning of November 2003. NBC started running our promos during Thanksgiving while I was in Youngstown visiting my family. Everyone was in awe. It was the first time I’d seen them since the show ended. My tagline was something like, “Omarosa comes from the cutthroat world of politics.” They were already packaging us and framing our characters to the American public. I was the tough political aide with a cutthroat attitude. Everybody I knew was fascinated by seeing me on television with billionaire Donald Trump. I got calls and notes from a lot of my old friends who said things like, “I knew you would be a star,” or “I knew you were going to do big things.” I’d always been ambitious, and all those years of hard work were paying off.
The show aired at the end of January 2004, and overnight, I went from anonymous to famous. The Apprentice was a mega hit, seen by more than twenty million viewers, and creative editing solidified my role as the supervillain, the person you loved to hate. I was a bit concerned about that. I was going for strong black woman, not angry black woman. There is a big difference. One of my former colleagues at CNN said not to worry about the portrayal. It would work out better being the villain. He told me, “I’m a big wrestling fan, and you have to remember that there is always a hero and a heel—and the heel is the most popular and sells the most merchandise. The heel also gets the biggest ratings and all the attention.”
I went to Times Square to try to see the promos NBC had running on the Jumbotron screens. The Apprentice was everywhere you turned in the Big Apple: on the side of buses, billboards, on top of taxis, in the subway, and in print ads in newspapers and magazines. It was surreal. I’d craved the success and the spotlight all my life, and there was no brighter, bigger spotlight than being on the inaugural season of Donald Trump’s reality show, produced by Burnett, the king of reality, on the number one network at the time, NBC.
On episode nine, teams gathered outside the Metropolitan Museum of Art to receive their task: choose “from a group of young emerging, brilliant artists” and sell the artist’s work at one of the city’s private galleries. The team that generates the most money wins; a difficult task given that art is subjective and there is no set market value. In the end, we only sold one piece for $869, while the other team sold eight pieces for thousands of dollars. Trump told me I had a big chip on my shoulder, was always making excuses, and had a “terrible attitude.” I got fired at the end of that epi
sode, but came back for the finale between Bill Rancic and Kwame Jackson. I supported Kwame in organizing a Jessica Simpson concert. Just as I’d predicted, Bill Rancic was hired as the first apprentice.
An estimated 27.6 million viewers tuned in to see Trump say to Rancic: “You’re hired!” in the season finale. He may have been the winner, but I earned “the ultimate pop-culture salute,” according to Today: I was spoofed on Saturday Night Live. My name became synonymous with the Trump brand and The Apprentice franchise. As soon as the final show aired, NBC offered me a talent development deal to create a talk show, to appear on soap operas and sitcoms.
Being the heel was working out quite well.
In interviews, Trump continued to give me a lot of the credit for the show’s success. He was very generous in his praise, and I responded to it. I was grateful for everything he’d done for me. The feeling was compounded whenever he gave me credit for his show’s success.
The first season of The Apprentice opened a whole new world for me, a career in entertainment. In 2004, I moved from DC to Los Angeles to pursue it full-time.
Trump and I stayed in touch through NBC. The network used me to campaign for The Apprentice to win an Emmy. I appeared on the cover of Variety, TV Guide, and Hollywood Reporter, my early adventures in surrogacy work, speaking in public on behalf of a person or entity.
For that TV Guide cover, Ereka Vetrini and I perched on the arms of the gilded chair with Trump sitting between us. We wore short skirts and Brioni ties with our shirts open. Trump was in a suit, as always. At that shoot, he paid particular attention to one of the magazine staffers. He was engaged to model Melania Knauss by then.
Trump told the TV Guide staffer how attractive she was and smiled at her in a way that could not be misinterpreted. It was the first time I’d seen this kind of behavior from him, but it wouldn’t be the last. Still, I chose to ignore it. His personal life was not my business. The TV Guide woman acted like she was flattered.
As I continued to do dozens of promotions and events with Trump on behalf of the franchise, I noticed a pattern emerge. Trump made no secret of his appreciation for beautiful women. And the women seemed to be appreciative of his overtures.
The Apprentice was nominated for an Emmy, and I was invited to the show. I dazzled on the red carpet in an orange Fushá gown by Haitian designer Marie Claudinette Pierre Jean, the wife of musician Wyclef Jean. We were in the reality category, up against The Amazing Race, American Idol, Survivor, and Last Comic Standing. We lost to The Amazing Race. Trump was in the audience with Melania. I saw him briefly as he was walking up the aisle to leave the auditorium, and he was livid. “We were robbed! They cheated us!” he said, in full voice. “I’m so pissed, Omarosa. They cheated us!” And then he was gone. That loss, and another two in 2005 and 2006, and then failing to earn a nomination again, infuriates him to this day.
I wasn’t upset. I was a huge reality TV fan. I knew that The Amazing Race had won the year before. And, although it sounds insincere, it really was an honor just to be nominated and to be in that room.
I hit the jackpot with The Apprentice. Trump and I both did. Our connection to the show, and to each other, was sealed.
* * *
I. Mr. Trump then went on to say, “And I will tell you, I went to the Wharton School of Finance, and I will say that I am sitting next to ‘it,’ ” and then pointed at Oprah. “There is nobody ever—ever—that has had ‘it’ more [than Oprah].” Perhaps back then, he didn’t think she was “insecure,” as he called her when #Oprah2020 was trending last year.
Chapter Three
* * *
The Ultimate Merger
I got to spend more time with Trump than any other Apprentice alum, doing promotions and photo shoots, but we never socialized outside of work. Although I believe I was his favorite, our interactions remained professional.
When he and Melania got married in January 2005, none of the contestants were invited to the wedding but I read all the coverage of the event. I remember being happy for them and hoping that it would last. I’d had many opportunities to observe their relationship at events. She would gaze at him with adoration. She loved him. Of that, I was convinced. Before him, she’d been a model, and now she was a billionaire’s third wife. As for his feelings, I wasn’t so sure.
In March 2006, Melania gave birth to Barron, Donald’s fifth child. If she had any idea about his extracurricular activities, I didn’t know, and again, it wasn’t any of my business.
I’d seen him at events that Melania did not attend—his birthday parties, fund-raisers at Mar-a-Lago, golf tournaments—and he behaved like a dog off the leash. He never hid his appreciation for beautiful women. We all know about Stormy Daniels, whom he met in 2006 at a charity golf event in Lake Tahoe, and Playmate Karen McDougal. It would be safe to assume that there were many others.
Only Melania knows the bargain she made in her own mind to tolerate her husband’s behavior. I will say that she is an incredible mother. She goes to all of Barron’s activities and school events and meets with all his teachers. I’ve seen them at Mar-a-Lago together and remarked on her adoring attentiveness and affection. She watches him running around with his friends, wipes dirt from his forehead, pulls him into hugs, and gives him kisses. The world doesn’t get to see this side of her, but I have, and I respect her deeply for it.
While the Trumps were newlyweds, my divorce became final and I was free to pursue my career full-on. The usual trajectory for a reality star is to burn hot and bright for about five minutes. But not for me.
I booked shows as often as I could, but I also had a balance. With my master’s, I lectured at colleges and taught seminars. Opportunities to do public speaking flowed my way, and I gave speeches about leadership in business and in life. Throughout my entertainment career, I’d been focused on relationship building. I learned in Washington that careers in politics were driven by connections. Why would entertainment be any different? When I did a show with a production company, I worked hard to build relationships, befriended the producers, the sound people, the camerapeople, the showrunners. So when they went to their next job and someone asked, “Who should we get for this show?” those same people would say, “Omarosa is amazing to work with. She gets it.”
I had name recognition. I established a reputation as the consummate professional. The relationships I brokered with producers, network executives, cast, and crew made it possible for me to go from one gig to the next. My fifteen minutes stretched into years. Some of Trump’s successful branding secrets—referring to himself in the third person and by one name, Trump—rubbed off on me. I insisted that people call me only by my first name, too.
I was still closely associated with The Apprentice and was often called to do promotional events for seasons that I didn’t have anything to do with. Hardly a casual observer, I kept an eye on how the show was performing in the ratings. Donald was obsessed with the ratings. I’ve heard that when the numbers declined, he became apoplectic. Then he’d do an interview and say that the show was still number one. Sound familiar?
Every year, the show dipped in popularity. Season one premiered in January 2004, and we had more than twenty million viewers. Season five premiered in February 2006, just two years later, and had fewer than ten million viewers. By season six, NBC had to scramble for a way to boost the ratings or face cancellation.
First, they tried moving the shooting location from New York to Los Angeles. The stunt failed. While the premiere attracted more than 9 million viewers, by the second episode, ratings plummeted to 7.3 million. During that season, one episode filmed at the Playboy Mansion in Holmby Hills, LA, the home of Trump’s longtime pal Hugh Hefner. At that taping, Trump met Playmate Karen McDougal. A photo exists of Karen, Ivanka, Melania, and Donald posing together with some other Bunnies, the craziest family snapshot in history.
According to a written statement of McDougal’s that was excerpted in The New Yorker, Trump complimented her, told her how beautifu
l she was—his MO—and got her number. They began speaking frequently on the phone, and soon after arranged to meet at the Beverly Hills Hotel in a private bungalow, where they began an affair that would last for about ten months, until April 2007, just after Barron turned one.
The Karen McDougal story eventually looped in another one of Trump’s longtime cohorts, David Pecker, owner of the National Enquirer, a man I’d had dealings with, too.
But I don’t want to get ahead of myself.
After the Los Angeles season tanked, NBC threatened to cancel The Apprentice. The Hail Mary idea was to change the name to The Celebrity Apprentice and have famous people compete for charity instead of a job in the Trump Organization. Trump called me to ask me to join the cast. “You made the show a hit before,” he said. “You can do it again.”
In January 2007, I went to a party for the first season of The Celebrity Apprentice at the Playboy Mansion along with some of the upcoming season’s contestants, network suits, production people, members of the Trump family, and a lot of naked women. The clothed people mixed and mingled, sipping their cocktails and snacking on hors d’oeuvres, as if it were completely normal for half the crowd to be practically or completely nude. I remember one Playmate was completely covered . . . in paint.
What kind of prime-time TV show would allow their launch party to take place at the Playboy Mansion? Who could get away with that? Only Donald Trump, because only he would think to do it or want to do it, and no one would dare say no to him.
Throughout the 2016 campaign and his presidency, many pundits have talked about the dangers of “normalizing” Trump’s offensive, inappropriate, provocative comments and behavior. But for as long as I’ve known the man, being offensive, inappropriate, and off-color is normal for him. The longer you live in Trumpworld, the more normal things like a work party at the Playboy Mansion seem to you. The Apprentice events were always populated with celebrities and models and his family. It wasn’t so far a leap to include nude models and porn stars. I made the rounds, skirting the grotto because God knows what went on in there, and talked to anyone who wasn’t in a thong.
Unhinged: An Insider's Account of the Trump White House Page 5