You’ve probably seen the headlines or the late-night social media threads. In a political climate where every past move is scrutinized under a microscope, one specific bit of trivia often resurfaces: the time Donald Trump dated a Black woman. Or, more accurately, a biracial supermodel who was one of the biggest faces in the fashion world during the 90s.
Her name is Kara Young.
If you weren't following New York City’s Page Six in the late 1990s, you might have missed it. But for about two years, between his high-profile divorce from Marla Maples and his eventual meeting with Melania Knauss, Young and Trump were a serious item. This isn't just internet lore or a weird "gotcha" fact; it's a documented relationship that tells a much more nuanced story about the man who would eventually become the 45th President.
Who Is Kara Young?
Kara Young wasn't just "some model." She was everywhere. Born in San Francisco to a Black mother and a white father, she became a powerhouse in the industry. We’re talking three solo covers of Vogue. She was an original Victoria’s Secret model, a face for Revlon’s "Most Unforgettable Women" campaign, and a regular in the pages of Elle and Glamour.
Basically, she was an A-list star in the fashion world.
She met Trump at a party in the Hamptons around 1997. At the time, Trump was newly single. He’d just split from Maples and was doing what billionaire bachelors in Manhattan do—attending high-end parties and looking for the next big thing. He pursued her, and they eventually began a relationship that lasted roughly two years.
The Dynamics of the Relationship
Honestly, the relationship was pretty public. They were photographed at movie premieres, like the screening of The Boxer in 1998, and they were a fixture at Studio 54 events.
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In a 2017 interview with the New York Times, Young looked back on those years. She described Trump as funny and said he had a "really good personality," which she admitted might be hard for people to believe given his later political persona. She also noted that while he didn't have many close Black friends, he frequently moved in circles with Black celebrities like Russell Simmons and Sean "Puffy" Combs.
But it wasn't all sunshine and red carpets.
The Intelligence Comment
A story that gained a lot of traction, especially after Maggie Haberman’s book Confidence Man came out, involved a comment Trump allegedly made after meeting Young’s parents. According to the account, Trump told Young she got her beauty from her mother (who is Black) and her intelligence from her father, "the white side."
Young later confirmed this happened.
She told Inside Edition that she didn't take it as a fight, but she did shut it down immediately. "No. Don't say that, it's not funny," she recalled telling him. He supposedly brushed it off as a joke. It’s one of those moments that critics point to as evidence of a deep-seated racial bias, while defenders see it as a typical, if clumsy, Trump-style "joke."
The Howard Stern Factor
You can't talk about Trump in the 90s without mentioning Howard Stern.
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Trump appeared on Stern’s show frequently, often bragging about his dating life. In one particularly chaotic segment, he got into a verbal spat with gossip columnist A.J. Benza. Benza claimed Trump "stole" Kara Young from him. Trump, in classic fashion, didn't just deny it—he gloated.
He told Benza that while the columnist was flying to California thinking Young was still his girlfriend, she was actually somewhere else (implying she was with Trump). It was peak 90s tabloid drama, involving two grown men fighting over a supermodel on national radio.
Why This Matters Now
People bring up the fact that Donald Trump dated a Black woman for different reasons.
- Supporters use it to argue against accusations of racism. Their logic is simple: "How can he be racist if he dated a biracial woman for two years?"
- Critics look at the specific comments he made during the relationship—like the "white side" remark—as proof of an underlying belief in racial stereotypes, even regarding people he cares about.
Young herself has been somewhat protective of the relationship while remaining honest about the man she knew. She hasn't joined the ranks of those "canceling" him, but she also hasn't ignored the controversial things he’s said and done since entering politics. When asked about his comments following the Charlottesville protests in 2017, she was subtle. She didn't defend him, but she also didn't attack him, essentially saying that people can see who someone is by the comments they make.
Amicable Endings and Billionaire Life
The relationship ended around 1999. It wasn't some explosive tabloid breakup involving cheating or lawsuits. According to Young, it just ran its course. Shortly after, she met billionaire Peter Georgiopoulos, whom she eventually married.
Interestingly, Young and Trump stayed on decent terms. She even called him on election night in 2016 to congratulate him on winning the presidency. It was a "congratulate an old friend" kind of move.
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Understanding the Timeline
If you're trying to piece together the history, here's the basic flow of how it went down:
- Late 1990s: Meets Kara Young in the Hamptons.
- 1997-1999: The couple dates seriously, appearing at major NYC social events.
- 1999: They break up.
- Late 1998/1999: Trump meets Melania Knauss (there was a slight overlap where he was seeing different people).
- 2016: Young calls Trump to congratulate him on the presidency.
- 2017-2022: Young gives rare interviews clarifying their history as the public becomes obsessed with Trump's past.
Key Takeaways for the Curious
If you're researching this topic to get a better handle on the "real" Donald Trump, keep these things in mind.
First, look at the primary sources. The most reliable information comes directly from Kara Young’s interviews with the New York Times and Inside Edition. Avoid the meme-ified versions of the story you see on TikTok or X, which often exaggerate the details to fit a specific political narrative.
Second, recognize the nuance. Relationships are rarely black and white (pardon the pun). You can have a "good relationship" with someone and still experience moments of racial insensitivity. Young’s experience suggests that Trump’s views on race are complex and often filtered through his own brand of "humor" and social status.
Lastly, realize that for Kara Young, this was a chapter of her life that ended over 25 years ago. She has moved on to a successful life as an entrepreneur (she co-founded the haircare line Hair Rules) and a philanthropist. She has explicitly stated that she wants her 2022 interview to be the last time she speaks publicly about the relationship.
Actionable Insights
- Verify the Quotes: When you see people claiming Trump said specific things to Young, cross-reference them with Maggie Haberman’s Confidence Man. Most "leaked" details actually come from this meticulously reported book.
- Contextualize the Era: Remember that NYC in the 90s was a very different social scene. Trump’s behavior was often viewed through the lens of a "playboy mogul" rather than a political figure.
- Check the Timeline: People often confuse the timing of his marriages. He was divorced from Marla Maples but not yet married to Melania when he dated Young.
To dig deeper into how these past relationships influenced his public image, you might want to look into the 1990s NYC tabloid archives, particularly The New York Post's Page Six, which chronicled their various appearances together in real-time.