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Fail Forward: The Lessons of Omarosa

A villain straight out of reality television central casting parlayed her infamy on ‘The Apprentice’ into a position at the White House

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Welcome to Reality TV Week at The Ringer! In addition to celebrating the best characters in the genre’s history, we’ll also be remembering some of its most iconic moments and characters, including, of course, the genre’s notorious villain turned political operative, Omarosa.


Sixteen years ago, Donald Trump fired Omarosa Manigault Newman—then Omarosa Manigault-Stallworth—from The Apprentice in the ninth week of the show’s debut season. She antagonized too many other contestants too frequently. She made too many excuses for her own shortcomings. She couldn’t lead. She had to go, though she’s never quite exited Trump’s boardroom, has she?

In “The Rime of the Ancient Mariner,” the 19th-century English poet Samuel Taylor Coleridge described the cosmic punishment for a sailor who shoots down an albatross. The sailor must wear the fallen seabird around his neck, carrying the burden as penance. In a similar sense, Omarosa would hang on to Trump: Ingloriously, she resurfaced in the first season’s finale to sabotage her own team leader Kwame Jackson’s efforts to organize a Jessica Simpson concert at the Trump Taj Mahal in Atlantic City, New Jersey. There, Omarosa proved her roundabout victory on The Apprentice, and in competitive reality TV in general, as the memorable loser, the chaos agent, the calamity from central casting, the telegenic trickster with a heart of dark matter. “You should’ve fired her,” Trump told Jackson in the climactic board meeting when he hired his winner, Bill Rancic.

Who remembers Bill Rancic? Who remembers Kwame Jackson? Who can I pay to erase Omarosa from the historical record altogether? Unbelievably, Trump recruited Omarosa into his White House, a political clusterfuck that has proved as treacherous, dysfunctional, and yet as durable as the respective Trump and Omarosa brands. The style guide compels me to name Manigault Newman upon subsequent mentions, and yet the more grandiose conventions in Greek mythology and Hollywood stardom compel me to invoke only her first name: Omarosa.

No doubt, Omarosa would lose every competitive reality TV program listed in The Ringer’s bracket this week: Survivor, American Idol, The Great British Baking Show, Big Brother, and, of course, The Apprentice, which, in fact, Omarosa lost thrice, the second and third times competing in The Celebrity Apprentice. She lost Celebrity Big Brother, too, but not before disavowing Trump, hyping her “tell-all” memoir, and having an asthma attack—all on camera. A month before her Big Brother exit, Trump’s former chief of staff, John Kelly, evicted Omarosa from the Eisenhower Executive Office Building in Washington, D.C., ending her tenure as Trump’s “political aide,” an appropriately ambiguous title befitting an administration defined in large part by its lack of accountability for anything. Her dismissal came after two years of Trump’s critics, as well as her own colleagues, wondering what, exactly, Omarosa does. I’ll tell you what she does. In New York, Washington, and Los Angeles, Omarosa climbs among the naive civilians and D-list celebrities who, inevitably, wish they’d never met her. (Remember, Trump was a washed-out real estate tycoon before NBC launched The Apprentice in January 2004.) Alongside Trump, Omarosa has embodied every cynical theory about modern celebrity’s stranglehold on the general attention span. “I would have evicted me five evictions ago,” Omarosa told the Big Brother host Julie Chen. “I can’t believe I lasted this long.”

The more conventional role models for reality TV stardom churn out seasons while expanding the core performance to incorporate costars, spinoffs, and household products; bonus points for bonus intrigue, such as Kim Kardashian nursing her husband Kanye West’s feud with Taylor Swift. Meanwhile, Omarosa doesn’t anchor her own TV series, and I can’t imagine she ever could: She thrives on her knack for materializing, with the determination of an ancient curse, just to wreck other people’s shit. Man plans, and Omarosa laughs. She haunts unsuspecting viewers who thought they were tuning into the evening news only to realize they were watching The Apprentice for several new seasons past its cancellation. Since leaving the White House, Omarosa haunts Trump, who has most recently described Omarosa as “disgusting and foul-mouthed,” and he’s currently suing her for violating her nondisclosure agreements in her political memoir, Unhinged: An Insider’s Account of the Trump White House. Who could have foreseen such betrayal from Omarosa Manigault Newman?! “I gave her every break,” Trump tweeted, “despite the fact that she was despised by everyone.” Ah! well a-day! what evil looks / Had I from old and young! / Instead of the cross, the Albatross / About my neck was hung.

In the two years since she exited the Big Brother house in the Hollywood Hills, Omarosa has withdrawn from the Washington political scene, biding her time, reconfiguring her allegiances, filing her knives, and, presumably, preparing to throw her hands around the neck of some new, unfortunate partner on Dancing With the Stars.