If you haven't been keeping tabs on the Mar-a-Lago seating charts lately, you might have missed the seismic shift in the Trump family's inner circle. For years, Donald Trump Jr. and Kimberly Guilfoyle were the ultimate MAGA power couple. They were everywhere—center stage at rallies, lighting up social media, and basically acting as the primary surrogates for the 45th (and now 47th) President.
But things look a lot different in 2026.
The engagement is off. The $9.7 million Jupiter mansion? Still has both their names on the deed, but it's reportedly gathering dust. Honestly, the split was one of those "quiet until it wasn't" situations that left a lot of people wondering where the fire started. If you're looking for the typical celebrity "conscious uncoupling" statement, you won't find it here. This was a classic high-stakes political breakup with a side of diplomatic relocation.
The Split Nobody Saw Coming (But Everyone Suspected)
Rumors started swirling back in late 2024. People noticed they weren't appearing together as often, and the high-energy "The Best is Yet to Come" vibes seemed to be replaced by a noticeable distance. By December 2024, the writing was on the wall. While the public was focused on the transition of the new administration, Don Jr. was increasingly spotted in the company of Palm Beach socialite Bettina Anderson.
By the time 2025 rolled around, the "engagement" with Kimberly was essentially a ghost.
It’s kinda wild when you think about it. They were together for six years. They got engaged on New Year's Eve in 2020, though they kept it under wraps until 2022. For a while, it seemed like Kimberly was the permanent fixture in the Trump dynasty. She had the look, the voice, and the absolute loyalty. But sources close to the family—the kind that talk to People and Page Six—suggested that the Trump inner circle eventually found her "grandstanding" a bit much.
Essentially, she was taking up too much of the spotlight that the family prefers to keep for themselves.
The Greece "Promotion"
In a move that many political analysts call a "velvet exile," President Trump nominated Kimberly Guilfoyle to be the U.S. Ambassador to Greece in December 2024.
Think about that for a second.
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You’re the fiancée of the President’s eldest son, and suddenly you’re being shipped off to Athens. She was confirmed by the Senate in September 2025 and officially moved into the Jefferson House (the ambassadorial residence) in November. On one hand, it’s a massive professional win. On the other, it’s about 5,000 miles away from Mar-a-Lago.
Where Donald Trump Jr. Stands Today
Don Jr. didn't stay single for long. Actually, he didn't stay single at all.
On December 15, 2025, during a Christmas reception at the White House, President Trump himself spilled the beans: Don Jr. is engaged to Bettina Anderson.
Bettina is a different vibe entirely. She’s a Palm Beach regular, well-connected in the social scene, and significantly less "loud" in the political arena than Kimberly was. Reports from early 2026 suggest Don Jr. has "essentially moved in" to Bettina’s Palm Beach townhouse. His car is always there. The $9.7 million home he bought with Kimberly in Jupiter? It’s basically sitting in real estate limbo while they figure out how to untangle their shared assets.
The "Special Bond" and Public Reactions
Kimberly finally broke her silence on the new engagement in early January 2026. Speaking with The New York Times, she kept it classy—or at least, diplomat-level professional.
"I’m happy for Don," she said. "I wish him, of course, all the best."
Short. Sweet. A little bit chilly? Maybe.
Insiders claim she’s actually pretty skeptical of the new match. There’s a sense that she doesn’t think Bettina is "built to last" in the high-pressure cooker of the Trump family. But honestly, Kimberly is busy. She’s currently the "talk of Athens," hosting diplomats and reportedly telling Greek officials she’s on the lookout for a new husband. She’s 56, thriving in a new country, and seems to have embraced the "living well is the best revenge" mantra.
Business and the Family Business
Don’t think for a second that the breakup slowed down the business side of things. Don Jr. and his brother Eric launched Trump Mobile in June 2025. It’s a "bring your own phone" carrier with a $47.45 monthly plan—a tip of the hat to the 47th presidency.
They’re also neck-deep in crypto ventures and real estate projects in Saudi Arabia. The Trump brand is more commercial than ever, and Don Jr. is at the helm of most of it. While Kimberly was once a key fundraiser and advisor, her role has been completely replaced by her diplomatic duties. The professional tie has been severed just as cleanly as the personal one.
The Complex Legacy of Donald Trump Jr. and Kimberly Guilfoyle
When we look back at the era of Donald Trump Jr. and Kimberly Guilfoyle, it marks a specific time in the MAGA movement. It was the era of the "unfiltered" surrogate. Kimberly’s 2020 RNC speech—the one that launched a thousand memes—was the peak of that energy.
But political dynasties evolve.
The shift to Bettina Anderson suggests a move toward a more "traditional" socialite presence in the family, or at least a desire for less internal competition for the microphone. Kimberly, meanwhile, has proved that she can’t be sidelined easily. She turned a breakup and a distant posting into a high-profile diplomatic career.
Key Takeaways for the Curious
- The Status: They are officially split. Don Jr. is engaged to Bettina Anderson (as of Dec 2025).
- The Career: Kimberly is the U.S. Ambassador to Greece, living in Athens.
- The Assets: They still co-own a nearly $10 million mansion in Jupiter, Florida, though neither appears to be living there.
- The Family: The Trumps have publicly embraced Bettina, with the President reportedly happy with the "new look" of the couple.
If you’re following this story, keep an eye on property records in Jupiter. The moment that mansion hits the market, you’ll know the final legal threads of the Donald Trump Jr. and Kimberly Guilfoyle era have finally been clipped. For now, they are two powerful people moving in completely different orbits—one in the social circles of Palm Beach, the other in the diplomatic halls of Athens.
To stay updated on these developments, you should monitor official diplomatic dispatches from the U.S. Embassy in Greece for Kimberly’s professional moves, and follow SEC filings or business press releases regarding "Trump Mobile" for the latest on Don Jr.’s commercial ventures.