It is a weird, surreal image to wrap your head around. Before the white Ford Bronco, before the gold elevator at Trump Tower, and long before the political landscape of America was fundamentally reshaped, Donald Trump and O.J. Simpson were actually friends. They weren't just casual acquaintances. They were the kind of New York "it-crowd" buddies who shared steak dinners, played golf rounds, and attended each other's weddings.
Honestly, looking back at it now feels like peering into a strange alternate dimension.
But the relationship between Donald Trump and O.J. Simpson is more than just a piece of 1990s trivia. It’s a case study in how fame, ego, and the American justice system intersect. When news broke that O.J. Simpson passed away in April 2024, the internet immediately started digging up old clips. Why? Because the parallels between their lives—rich, powerful men navigating massive public trials—are almost too loud to ignore.
The Wedding Guest List and the Golf Course
Let’s get into the specifics. In 1993, O.J. Simpson was a guest at Donald Trump’s wedding to Marla Maples. There’s actually footage of O.J. on the red carpet that night at the Plaza Hotel. He’s smiling, talking to reporters, and saying how much he hopes the relationship works because the couple had been through "so much turmoil."
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At the time, Simpson was "The Juice"—the beloved Heisman winner and movie star. Trump was the billionaire comeback kid. They fit together. They were both fixtures of the 1980s and early 90s celebrity circuit where money and status were the only real currency.
Trump later told Howard Stern that he played quite a bit of golf with O.J. back then. He described Simpson as a "fun guy," though his tune changed drastically once the double murder trial of Nicole Brown Simpson and Ron Goldman took over the world.
That 2008 Howard Stern Interview
If you want to know what Trump really thought about O.J. after the trial, you have to look at his 2008 appearance on the Howard Stern Show. Trump didn't hold back. He told Stern, "I realized he killed his wife." He even went as far as to say he "hated" the fact that O.J. was acquitted.
"I don't like people that kill their wives," Trump said bluntly. "Does that make sense? Does that make me a disloyal person?"
It was a rare moment where Trump seemingly drew a hard line in the sand regarding a former friend. But, in classic Trump fashion, there was a twist. Despite believing O.J. was a murderer, Trump still wanted to hire him.
The Celebrity Apprentice Plot That NBC Blocked
This is the part that sounds like a fever dream. In the mid-2000s, when The Apprentice was the biggest thing on TV, Donald Trump actually pitched the idea of having O.J. Simpson as a contestant.
Think about that.
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Trump knew it would be a ratings goldmine. He told Stern that NBC "went totally crazy" when he brought it up. They basically had a collective heart attack at the thought of putting a man most of the country viewed as a killer back on prime-time television. Trump’s logic was simple: 35 million people would have watched. To him, the numbers justified the controversy. NBC, obviously, disagreed, and the casting never happened.
Why the Donald Trump and O.J. Simpson Comparison Won’t Die
You can't talk about these two without talking about the "Trial of the Century" vs. Trump’s various legal battles in 2024 and 2025. Commentators like Chris Cuomo have spent hours breaking down the similarities.
Both men represent a specific kind of American archetype: the celebrity who is larger than the law.
- Jury Nullification and Polarization: The O.J. verdict split the country down racial lines. People didn't just disagree on the facts; they lived in different realities. We see the exact same thing today with Trump’s trials. Your opinion on his guilt often has more to do with your zip code and news feed than the actual evidence presented in court.
- The Power of the Brand: O.J. survived as long as he did because of the "Juice" persona. Trump survives because of the "MAGA" brand. Both understood that if you have a loyal enough base, the truth becomes secondary to the narrative.
- The "Tough" Persona: There’s a disturbing anecdote Trump once told about seeing O.J. and Nicole at a dinner. He claimed Nicole was being "rough" on O.J., and then he laughed, saying, "So he decided obviously to kill her." It was a dark, off-the-cuff joke that showed how Trump viewed the dynamics of power and aggression in relationships.
What Happened When O.J. Died?
When O.J. Simpson died in April 2024, the reaction from the Trump camp was notably quiet. There was no "Rest in Peace" post on Truth Social. By that point, O.J. was a ghost of a former life Trump had long since moved on from.
Interestingly, a weird gaffe happened in the LA Times obituary for Simpson. The writer accidentally swapped the name "Simpson" for "Trump" in one of the final paragraphs. It was a Freudian slip that went viral instantly, perfectly capturing how much these two figures are linked in the American subconscious.
Actionable Insights: What This Means for Us
So, what do we actually do with this information? It’s easy to get lost in the gossip, but there are real lessons here about how we consume news and justice.
- Audit Your Information Bias: Just like in 1995, we are prone to picking sides before a trial even begins. If you find yourself instantly dismissing or accepting a legal "fact" because of who the defendant is, take a step back.
- Recognize the "Ratings" Trap: Trump's desire to put O.J. on The Apprentice proves that media often prioritizes shock value over ethics. Be wary of news cycles that feel like entertainment—they usually are.
- Understand the "Teflon" Effect: High-profile figures don't play by the same rules. Whether it’s Simpson or Trump, wealth buys a level of legal defense that the average person can’t fathom. Recognizing this disparity is the first step toward demanding a fairer system.
The "friendship" between these two ended decades ago, but the cultural shadow it cast is still very much with us. They are two sides of the same coin—a coin that keeps getting tossed in the air every time a high-stakes trial hits the headlines.
To dig deeper into how these legal strategies have evolved, you should look into the history of "jury nullification" in high-profile celebrity cases; it explains a lot more about the O.J. verdict than the DNA evidence ever could.