You remember 2012, right? Neon was in, Instagram was just starting to ruin our attention spans, and Donald Trump was still just a guy on NBC firing people in a boardroom with gold-plated trim.
But if you were watching The Celebrity Apprentice Season 5, you weren't looking at the skyline. You were looking at Aubrey O’Day.
She was fresh off the Danity Kane breakup—the first one, anyway—and she arrived on that set like a hurricane in a bodycon dress. Honestly, people still talk about her performance because it was, well, exhausting. She was brilliant. She was "vicious." She was apparently the only person in the room who realized that being a "team player" is a great way to lose a reality show.
The Genius (and Drama) of Aubrey O'Day on the Apprentice
Let’s be real: Aubrey didn't just participate in The Celebrity Apprentice. She tried to take it over.
While other contestants like Arsenio Hall or Clay Aiken were trying to play the "respect the legacy" game, Aubrey was treats every task like a life-or-death branding exercise. She had this degree in political science from UC Irvine, and you could tell. She understood the optics. She understood the hustle.
The media at the time was brutal to her. They called her narcissistic. They called her a "villain." But if you actually re-watch those episodes, you see a woman who was consistently the most creative person in the room. Even her teammates who hated her—and let’s be honest, Arsenio Hall really hated her—had to admit she worked harder than everyone else combined.
That Moment She Almost Quit (But Went to Church Instead)
One of the wildest moments in Apprentice history happened during a three-hour special. After being absolutely berated by her team for not being a "team player"—even though they won the task—Aubrey actually walked off the set.
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She headed straight for those famous elevators. Usually, when you go down those elevators, you're fired. You're gone.
The internet went nuts. Then, she hopped on Twitter (now X) and basically said, "Lol. I went to church! I stay!"
It was a total power move. She basically told the producers and Donald Trump that she would leave on her own terms, not theirs. She eventually came back and clawed her way to the final three, becoming the last woman standing in a season dominated by huge male personalities.
The Donald Trump Jr. Connection: What Started on Set
You can't talk about Aubrey O'Day Apprentice history without mentioning the elephant in the room. Or rather, the son in the boardroom.
This is where things get messy. Reports later surfaced that Aubrey and Donald Trump Jr. began an affair during the filming of the show in 2011. Don Jr. was an advisor on the show at the time, sitting right there next to his dad.
According to Aubrey, they were soulmates. She’s been very open lately—specifically on Michael Cohen’s podcast—about the details. She claims they first had sex in the bathroom of a gay club in New York after the show wrapped. Apparently, he even called her "Spanky" because she was wearing Spanx that he couldn't get off.
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Kinda weird? Yeah. But it adds a completely different layer to those boardroom scenes. When you watch them back now, knowing they were allegedly writing love letters to each other behind the scenes, the tension is palpable.
- The Discovery: The affair reportedly ended in 2012 when Don Jr.'s then-wife, Vanessa, found "sexy" texts from Aubrey on his phone while he was in the shower.
- The Music: Aubrey’s song "DJT" is widely believed to be about the breakup. The lyrics are pretty devastating if you know the context.
- The Aftermath: While the Trumps have mostly stayed silent, Aubrey has never really stopped talking about it. She’s called him the person she "fell in love with," but says the man he is now isn't that person.
Why She Was Actually Fired
Despite being the "Super Apprentice," as some fans called her, Aubrey didn't win. She finished third.
Trump fired her because his advisors, like Marlee Matlin and John Rich, felt she was "transparent." They thought she was too young, too inexperienced, and maybe a little too focused on herself.
Was she? Maybe. But she also raised a ton of money for GLSEN, a charity that fights bullying against LGBTQ+ youth. It was a bit ironic, considering how much she felt she was being bullied by the older celebrities on the show.
Arsenio Hall famously called her some pretty choice words in the boardroom. Clay Aiken wasn't much nicer. They saw her as a threat because she was. She was the only one who didn't care about making friends.
Actionable Insights for the Modern Hustler
Whether you love her or think she was the ultimate reality TV villain, there’s actually some stuff to learn from the Aubrey O'Day Apprentice era.
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First off, don't be afraid to be the smartest person in the room. Aubrey’s ideas were often the ones that won the tasks, even if she took all the credit. In business, results often matter more than being liked, though a little diplomacy goes a long way.
Second, understand the game you are playing. Aubrey knew she was on a reality show. she gave them drama, she gave them ratings, and she gave them work. She made herself indispensable until the very end.
Lastly, keep your receipts. Aubrey’s longevity in the news cycle—even 14 years after the show—is because she remembers everything. Whether it's the Diddy drama or the Trump affair, she knows that in the entertainment world, your story is your currency.
If you're looking to revisit this era, most of the Season 5 highlights are still floating around YouTube. It’s a fascinating time capsule of a pre-politics Trump and a pre-filter Aubrey O'Day. Just be prepared for a lot of shouting and some very questionable 2012 fashion choices.
To get the full picture of Aubrey's perspective today, you should listen to her 2023 interview on the Mea Culpa podcast or look up her recent statements regarding her time with Danity Kane. It's a long way from the boardroom, but the fire is still there.