I left the White House with the Clintons, and took a job working with my Howard classmate Cleve Mesidor in the CNN newsroom. As a newsroom assistant, I delivered scripts, researched archived footage, and performed any task that Greta Van Susteren, Judy Woodruff, and Bernard Shaw put before me. It was an action-packed job during a terrible time for CNN. They were laying many employees off, and getting a permanent job was too difficult at that time. I went to the career-services office at Howard University Graduate School for assistance. The director told me about a job posting for a director of research and development at the National Visionary Leadership Program, a foundation for historically black colleges. I was surprised to discover that the foundation was founded by none other than Bill Cosby and his wife, Camille.
I interviewed and got the job. I reported to his wife. I only interacted with Mr. Cosby a handful of times in my entire year at the foundation.
As the director of research and development, I was tasked with identifying programs and individuals at historically black colleges and universities to receive scholarships and grants. It was a perfect job for me! While there, I helped to compile a tremendous video archive of civil rights leaders, community activists, and other remarkable people.
During my year at the foundation, I took a week off to compete in the Mrs. United States pageant in Hawaii. (I was married to my Howard University sweetheart at the time and was the reigning Mrs. DC.) One morning during the competition, we all woke up to the news that planes had flown into the Twin Towers in New York City and the Pentagon in Washington, and another plane had gone down in Pennsylvania. Flights to DC were canceled for a week. I was stuck in paradise . . . and miserable. I remember aching to grieve and mourn with my family and friends in my adoptive hometown, and reflecting on what really mattered in life, as we all did. I was proud of my work at NVLP and was eager to get back into politics.
One of my closest friends in Washington was Kevin L. Jefferson, who was working at the Democratic National Committee (DNC). When he needed help with the African American Leadership finance council, he called me, and I saw this as my chance to get back into the political arena and to make a difference.
I became one of the vice chairs of the council along with my dear friend Ervin Bernard Reid. The chairman of the DNC then was Terry McAuliffe. McAuliffe had deep ties to the Clintons, having been Bill Clinton’s chief fund-raiser for many years. I was reunited at the DNC with Donna Brazile, who landed there after Gore’s 2000 electoral-college loss to George W. Bush. The defeat had been devastating, and the DNC was trying to rebuild and figure out what went wrong. One of McAuliffe’s initiatives during my two years at the DNC was to compile a database of 170 million people who were likely to vote Democratic in upcoming elections, a.k.a. “Demzilla.”
Kevin Jefferson, Ervin Bernard Reid, a political operative in DC, and I traveled the country doing fund-raisers for the DNC. One memorable event that I helped organize was at a private home on the South Side of Chicago: Maurice and Vietta Johnson hosted two hundred people in their backyard, including a young state senator by the name of Barack Hussein Obama. I noticed him as soon as he walked in the door with one of my Howard University classmates, Vera Baker. As Obama worked the crowd, she told me he was an up-and-coming political star and that we needed to support him. In his book What a Party! My Life Among Democrats, Terry McAuliffe recalled how Obama came up to him at the event, shook his hand, and said: “I’m going to be the next United States senator from Illinois.” McAuliffe was impressed with the young politician’s poise and intelligence and remembered thinking, Why not? Although he wasn’t yet the Barack Obama we know now—he wore a rumpled suit and seemed very eager to talk to the DNC heavy hitters—he had presence.
By 2003, after five years in politics, I was disillusioned. My White House stint had ended with impeachment and Gore’s heartbreaking election loss. My DNC experience showed me just how dependent politics were on fund-raising, which made the entire enterprise suspect. I saw little but corruption, bad behavior, backstabbing, and abuses of power. I was ready to make another move, but I didn’t know what or where.
I was ripe for suggestion when Kevin came into the office one day and asked me if I’d seen the casting notice soliciting contestants for a reality TV show called The Apprentice, hosted by his business hero, Donald Trump. “You should apply and try to win so you can go work for Trump,” Kevin insisted.
Everyone in DC was talking about it. The show was going to be produced by Mark Burnett, the man behind Survivor, a true cultural phenomenon. We lived in a divided nation even then, but it seemed like everyone in America cared about who was voted off the island at tribal council each week.
While my male colleagues talked about what they’d do with The Apprentice $250,000 prize money, I went online and researched the show. I’d studied Donald Trump while I was in business classes at Central and was vaguely interested in him because as an avid golfer, I knew he owned a handful of luxury golf courses; and as a former beauty queen, I knew he owned the Miss USA pageant.
The application deadline was coming up in one week, on a Friday, but because of all my obligations—marriage, job, church—I waited until Thursday to make my audition tape. A friend from Howard helped me shoot it. I overnighted it just in time to make the deadline.
My audition tape touted my career in politics. I said something like, “Government is the biggest business of them all. Nobody comes to the table with more business acumen than someone who’s worked for the biggest employer in the country!” Emphasizing my political résumé was strategic. How many of the other applicants had White House experience? I assumed that the majority of contestants would be Ivy Leaguers, Wall Streeters, in real estate, or PR people.
The more I learned about the show, the more confident I felt about applying. I had the newscaster voice and beauty queen posture I’d cultivated since childhood, discipline from ROTC, good timing from acting in high school and college. From sports, I’d learned to be a fierce competitor. I had a solid career at that point in my life and had absorbed lessons from each job about office politics, difficult colleagues, and logistic and organizational skills.
From the moment I sent in my tape, I felt certain I’d get picked for an audition. So when I got the call that I’d made the first cut, I almost said, “What took you so long?”
* * *
I. I was fortunate to be able to meet Reverend Jackson again years later while at Howard University, and once more in the Clinton White House, and I told him how much his speech meant to me.
Chapter Two
* * *
Winning Bigly
Donald Trump has spoken about the selection process, how he and Mark Burnett Productions cast the sixteen candidates to appear on season one of The Apprentice. He claimed there were 215,000 applicants, killers, Ivy Leaguers, all of them “terrific,” the best, the smartest, etcetera. My first meeting with the casting directors of The Apprentice took place in Washington, DC. The casting team was scouring the country in search of the perfect candidates for the show. I chose to wear one of my power suits from my White House days to the downtown hotel where they were set up. After sending in my audition tape a couple of weeks prior, I received a call saying that I would be given a specific interview time and that I would need to be there early. When I arrived at the hotel, I was surprised to see the line wrapped around the block with thousands of hopeful walk-ins, all also in suits.
I went into the bustling lobby to find the check-in table and was relieved to see a sign for slotted interview sign-ins. I gave my name and was escorted to another hold room and waited for my appointed time. When I walked in to the room, a geeky-looking guy with glasses introduced himself. “Hi, I’m Rob LaPlante,” he said.
“Hi, I’m Omarosa.”
“Omarosa what?” he asked.
“Just Omarosa!” I delivered the line with precision and sass.
During my interview (which was supposed to be only ten minutes), I talked about everything, from
working in the White House to the scars and stab wounds on my arms and scalp from fights I’d survived while growing up in the hood. The casting team looked captivated. When I left the interview almost an hour later, a girl escorted me out and said, “Definitely stand by for a callback!”
The call came the next week. The casting team invited me to Los Angeles for additional screening. I had made the cut.
Trump told Oprah on her show that, because of the huge number of applicants, his team had to rely, in part, on the luck of the draw. Oprah described what she looked for when she screened audition tapes: “There’s an energy, there’s a spark, there’s an essence, there’s a life that comes through in a matter of seconds,” she said. “And in five seconds, they decide if you even have anything worth listening to . . . There’s an indescribable ‘it factor’ that, you know, I don’t think you can teach. They don’t teach it in the Wharton School of Business.”I
Apparently, I had what Oprah would call “it.”
The cut of one hundred people was flown to Los Angeles for a round of interviews.
The first step was an extremely exhausting criminal background check that was on par with the one the FBI had conducted on me to work at the White House! Next, we were subjected to a physical checkup, which included a humiliating vaginal examination and Pap smear, as well as testing for sexually transmitted diseases. We then went through a series of psychological exams, which included an IQ test and personality assessments.
I asked the doctor about all the testing, and she stated that they were looking for red flags like depression or vulnerability, how someone might react under extreme conditions, and how they would deal with the pressure and demands of a round-the-clock twenty-four-hour intense production schedule. In one session, the psychologist asked me some additional questions because of the contradictory results of several tests. I asked her to elaborate. She explained that I had an unusual balance of femininity and masculinity in my outlook on the workplace. I was extremely feminine in my style, but my test scores showed that I strategized like the men and that my competitive nature was more aligned with traditional male perspectives. Think like a man, act like a woman!
They kept us locked in our hotel rooms for hours at a time, with no phones, computers, or contact with the outside world. I welcomed the time in LA as a much-needed break. While I was there for those interviews, I’d planned to size up the competition, but the producers made sure that none of the candidates ever saw one another. There was a veil of secrecy around the entire process, which I understood was part of the winning reality TV formula.
A few weeks later, the production company called to say I’d made the cast but swore me to secrecy about my participation. They supplied me with logistical info—dates, a packing list—but I only half listened. I was too excited; I believed this moment was the start of something monumental in my life. This could be my entrée to the New York business and entertainment worlds. The Donald Trump of 2003 was presented as the real estate maverick, the mogul. I thought I could learn so much from him. Of course, if I won, there’d also be that $250,000 prize. No matter what, appearing on the first season of The Apprentice would be a life-changing opportunity. Back then, it never occurred to me that doing a reality show would lead to my being the highest-ranking African American senior adviser in the White House to the president, Donald Trump, another fellow reality star. I don’t think anyone could have imagined that.
I had a short time to prepare before the show started taping in New York. Kevin and Ervin were so excited for me! They became my two drill sergeants and helped prepare me for the competition by buying me books and researching everything they could find about Donald Trump. I read Trump’s The Art of the Deal and The Art of the Comeback several times. I read every Trump magazine profile and interview. I watched videos of his TV interviews. The winner would be the person who understood Trump’s business style, his negotiation style, his machismo, his boldness, his brashness. To do that, I would need to become a mirror and reflect a female version of him. Imitation is the sincerest form of flattery, after all.
A friend who worked in production for several reality shows gave me some incredible advice before taping began. First, he said, “You can win without winning just by making sure no one forgets your name.” My father had done me the favor of giving me the unique Nigerian name Omarosaonee (I shortened it to Omarosa in school), which means “my beautiful child desired.” Sure, it wasn’t easy to pronounce, like Jill or Becky, but it was memorable.
Second, my friend said, “Reality TV is about conflict and tension.” He suggested that I should either be (1) starting a fight, (2) stirring one, or (3) breaking one up. “Whatever you do, be where the action is.”
Last, and the most important, he encouraged me to establish a television persona and own it. I intended to be confident and decisive, like Trump himself, but I would represent my community well as a strong black woman, proud of where she came from. I would be dignified and confident and execute my vision of success.
The promotion for The Apprentice was spectacular and started shortly after we wrapped shooting. The production and network spared no expense to make sure that every American knew about the show—and about the sixteen of us. Since my strategy was to emulate Trump, when they shot a promo of me and asked, “Do you think you’ll win?” I said, “Of course! I’m going to destroy the competition!” My transformation into the lady version of Trump was well under way.
Realistically, I knew that the very first Apprentice winner would not be a black woman. It was not that I lacked the confidence to win; I just understood the way things worked. But even with the odds against me, I still wanted to win. The question was, could I win the show without being the actual winner?
We were told to bring only a limited number of suitcases of clothes for a forty-day shoot. I’d competed in pageants my whole life, and I knew that would not be enough. Since most people were coming to New York City by plane, they had no choice but to deal with a two-bag limit. I was coming from DC on Amtrak, a train with no baggage restrictions. I showed up with seven bulging suitcases. No one said a word about it. They just hauled my stuff to the hotel and put it in my room.
All of the female contestants were young, slim, attractive, with long hair and/or blonde. I was the only African American among them, of course. The men were more diverse in terms of body type, but not race. Kwame Jackson was the only male African American, with an African name as well. In my first interactions, whenever people pronounced my name incorrectly, I said dramatically, “It’s Oh-mah-roe-sah,” embedding the sound in viewers’ minds.
I could mirror Trump’s attitude but I couldn’t copy his personal aesthetic. Amy Henry and Bill Rancic were my biggest competition, as I surmised, because they were cut from the same cloth as Trump, who was always using the term “central casting.” Amy was his type of woman, and Bill was his type of handsome man.
I had many famous lines to come out of the first season. For instance, I was the first person to say on a reality TV show the now-famous phrase “I’m not here to make friends.” My objective was to methodically eliminate each contestant, one by one, so why would I want an emotional attachment to any of them? How could you lobby Trump to fire your “friend” on national TV with millions of people watching?
Early on in the competition, I had a puzzling conversation with Katrina Campins, my roommate, when she kept insisting that she was going to be successful by making people like her and by being a nice person. I just looked at her, thinking, Good luck with that. But it wasn’t my job to teach her a better strategy.
I was at the center of most of the conflict on the show, by design, but I never raised my voice or called people names. I never got physical or aggressive, unlike some who called me everything in the book. I stayed cool, calm, and collected. And yet, the other women felt threatened by me. When a man is confident and stands up for himself, he’s called tough and strong. He’s a good businessman. When a woman plays to win, she’s labeled
a villain or worse. I was playing to win. I wanted the job running a Trump company (in reality, the winner would never run a Trump company; they would just be a project manager of a small deal) and I wanted the accolades that came with it. I needed to win, and I’m not ashamed to say it. A lot of the other candidates acted as if they were on an Apprentice missionary trip. I was straightforward about my stance, and it intimidated people.
Being provocative was good TV and led to huge ratings for the network. Many newspapers and magazines called me the “breakout star” of the show. Trump liked what I was doing. We were winning our time slot every week! Winning bigly. On private phone calls with me, and in many media interviews, he attributed the winning to me.
Winning is a prerequisite for entering Trump’s orbit, populated, almost exclusively, by people like him, entertainers who said things to get a reaction or garner attention. He cultivated these people and encouraged them to exaggerate the unique part of themselves and to live up to the hype. He saw the value in drama, aesthetics, conflict and theatrics, and in having a personal brand. The reason he often referred to himself in the third person was to reinforce the name of his brand. I started to do it as well.
The Apprentice was a branding opportunity for Trump, and nearly every task was self-promotional. Of course, the main location was in Trump Tower; this is where all the candidates were housed and the boardroom meetings on the show occurred. A giant sign for Trump Organization was right behind a secretary’s desk. And the winning team was promised an aerial tour of Manhattan on Trump’s private helicopter, which is also featured in the opening scenes. We would gather at a location in New York to receive a task from Trump. He would say something like, “Today you’re standing in front of my amazing Trump SoHo. It’s the greatest Trump hotel in the world. You’re going to sell condos in this building, the greatest building in the world,” etcetera. Or we’d gather in front of a delivery truck and he’d lift the side panel to reveal cases of Trump Ice, his water brand, that we were to sell.
Unhinged: An Insider's Account of the Trump White House Page 4
