It feels like just yesterday Kimberly Guilfoyle and Donald Trump Jr. were the undisputed "it" couple of the MAGA movement. They were everywhere. You couldn't scroll through a news feed without seeing them together at a rally or a high-stakes fundraiser.
But things changed. Fast.
Honestly, the shift was so quiet at first that most people missed it. While the world was focused on the 2024 election cycle, the foundation of their six-year relationship was basically dissolving in the background. Now that it’s 2026, the dust has finally settled, and the picture looks a whole lot different than that $9.7 million Jupiter, Florida, mansion they once shared.
The Split Nobody Saw Coming (Until It Was Too Late)
For a long time, it seemed like they were headed for a massive, televised wedding. They got engaged on New Year’s Eve back in 2020, though they kept it under wraps for about a year. People expected a spectacle. Instead, we got a slow fade.
By late 2024, the rumors were getting loud. Really loud.
There were whispers of public bickering at Mar-a-Lago—nothing explosive, just that "couple-at-the-end-of-their-rope" vibe where every little thing becomes an argument. Then came the photos. Don Jr. was spotted in Palm Beach holding hands with socialite Bettina Anderson.
That was pretty much the nail in the coffin.
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What's wild is that they never actually put out one of those "we have decided to go our separate ways" joint Instagram posts. They just... stopped being "Kimberly and Don."
Kimberly Guilfoyle and Don Jr: The New Reality in 2026
If you're looking for Kimberly today, you won't find her at a Trump campaign office in Florida. She’s roughly 5,000 miles away. In what some critics called a "promotion-banishment," President Trump nominated her as the U.S. Ambassador to Greece.
She officially moved to Athens in November 2025.
She seems to be leaning into the new role, too. During a meeting with Greek President Konstantinos Tasoulas, she even joked about being on the lookout for a "new husband." It’s a classic Kimberly move—bold, a bit cheeky, and signaling to the world that she’s definitely moved on.
Meanwhile, Don Jr. isn't exactly pining away.
In December 2025, during a Christmas reception at the White House, the President himself announced that Don Jr. is engaged to Bettina Anderson. It happened fast. Within a year of the split with Kimberly, Don was already planning another walk down the aisle.
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Why the Breakup Still Matters
Even though they've both moved on, their history is still tangled up in some very real ways.
- The Real Estate Problem: Records show that $9.7 million mansion in Jupiter is still registered in both of their names. Talk about an awkward property tax bill.
- The Family Dynamic: Kimberly was incredibly close to the Trump kids. She was basically a fixture at family dinners for years.
- The Political Legacy: Kimberly was one of the campaign's most effective fundraisers. Losing that "power couple" branding changed the optics of the inner circle.
What Most People Get Wrong About the Breakup
A lot of people think there’s a massive feud between them.
Actually, it's more complicated. In an interview with The New York Times in early January 2026, Kimberly said, "I'm happy for Don. I wish him, of course, all the best."
Sources close to her say she still has her doubts about his new relationship—she allegedly doesn't think Bettina is "built to last"—but the vitriol just isn't there publicly. They still share a "special bond," or at least that’s the party line.
It's a weirdly professional ending to a very public romance.
Lessons from the Kimberly and Don Era
If you’ve followed this saga, there are a few takeaways that are actually pretty useful for understanding how high-profile relationships work in the political spotlight.
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1. Public Perception vs. Private Reality
Just because a couple looks like a united front on a stage doesn't mean they aren't fighting in the car ride home. The "power couple" brand is a job in itself, and sometimes that job becomes too heavy to maintain.
2. The Power of the "Pivot"
Kimberly didn't just disappear after the breakup. She secured a major diplomatic role. Whether it was a way to give her a graceful exit or a genuine reward for her loyalty, it shows the importance of having your own identity and career path outside of a partner.
3. Timing is Everything
Don Jr.'s quick engagement to Bettina Anderson caught a lot of people off guard. It's a reminder that in these circles, the social and political calendar waits for no one.
Moving Forward
If you're still tracking the aftermath of the Kimberly Guilfoyle and Don Jr. split, keep an eye on the Jupiter property records. That's usually the first sign of a clean break. Also, watch Kimberly's work in Athens; she's likely to remain a significant voice in the "America First" movement, even from across the Atlantic.
To stay truly updated, look for official diplomatic releases from the U.S. Embassy in Greece rather than just tabloid rumors. The real story now is how she handles the Mediterranean stage while the Trumps continue their business in Washington.
Check the latest FEC filings if you're curious about whether Kimberly is still involved in the fundraising side of things. Often, these professional ties outlast the romantic ones by years.