You probably saw the photos. It’s December 2025, the White House is decked out for Christmas, and there’s Donald Trump Jr. at the podium. But the woman standing next to him isn’t Kimberly Guilfoyle. It’s Bettina Anderson, a Palm Beach socialite, and they’re announcing their engagement.
Wait, what?
If you feel like you missed a chapter, you aren’t alone. For years, Don Jr. and Kimberly were the inseparable, high-decibel face of the MAGA movement. They were the "power couple" who seemed destined for a massive Mar-a-Lago wedding. Instead, by the start of 2026, Kimberly is living in Athens as the U.S. Ambassador to Greece, and Don Jr. is planning a wedding with someone else.
Honestly, the split was one of the quietest breakups in one of the loudest families in America.
The Long Goodbye: How It Actually Ended
People always ask when it officially ended. The truth is, there wasn't a single "explosion." It was a slow fade that started way back in 2024. While the public still saw them together at campaign rallies, insiders at Mar-a-Lago started noticing the cracks. They were bickering in public—not screaming matches, just that low-level irritability you see in couples who have hit a wall.
By late 2024, the rumors were everywhere. Page Six was dropping hints that they were on "shaky ground." Then, things moved fast.
Shortly after the 2024 election victory, Don Jr. was spotted holding hands with Bettina Anderson. That was the "soft launch" of the breakup. There was no press release. No dramatic Instagram post. Just a sudden shift in the orbit.
Interestingly, the Trump family didn't "excommunicate" Kimberly. In a move that surprised some, Donald Trump nominated her to be the U.S. Ambassador to Greece in December 2024. Some saw it as a promotion; others saw it as a very polite way to put an ocean between his son and his ex-fiancée.
Kimberly in Athens and the "New Husband" Comment
Kimberly didn't just slink away. In typical Guilfoyle fashion, she reinvented herself. By November 2025, she was officially sworn in as the first female U.S. Ambassador to the Hellenic Republic.
She's apparently thriving there. Reports from Athens describe her as "the talk of the town," hitting the local club scene and working late nights with Greek ministers. She even made a joke during her credentials ceremony, telling Greek President Konstantinos Tasoulas that she was already on the lookout for a "new husband."
Talk about moving on.
Why the Engagement to Bettina Anderson Changed Everything
When the elder Trump announced Don Jr.'s engagement to Bettina Anderson on December 15, 2025, it felt like the final nail in the coffin for the "Donberly" era.
Don Jr. looked genuinely happy at the White House announcement. He even admitted he was "at a loss for words," which is rare for him. Bettina, who is 39 and has a background in the Palm Beach social scene, seems to fit a different vibe than Kimberly. While Kimberly was a "MAGA firebrand," sources say the family (including the President) likes that Bettina is a bit more low-key—well, as low-key as you can be while getting engaged at the White House.
But was Kimberly actually cool with it?
Publicly, she said the right things. In a January 2024 interview with The New York Times, she said, "I'm happy for Don. I wish him, of course, all the best."
Privately? Sources told People magazine she had "major concerns." She reportedly doesn't think the new relationship is "built to last" and felt the engagement was difficult to watch, especially since she and Don Jr. still had clothes and belongings at each other's houses as recently as late 2025.
The Business of Being a Trump Jr. in 2026
While his romantic life has been a whirlwind, Don Jr.’s professional life hasn't slowed down. He’s moved away from the day-to-day of the Trump Organization and into the world of venture capital and defense contracting.
As of early 2026, he’s a partner at 1789 Capital. This isn't just a hobby. One of the companies he backs, Vulcan Elements, recently scored a $620 million loan from the Pentagon. Another startup he's involved with, Unusual Machines, got a contract to build thousands of drone motors for the Army.
Critics call it "ethically dubious," but Don Jr. has brushed it off, focusing on his role as a bridge between the administration and the "America First" business world. He's also been busy on the international stage, recently visiting Greenland following his father’s renewed interest in purchasing the territory.
What Most People Get Wrong About the Breakup
The biggest misconception is that there’s "bad blood."
Don Jr. actually posted a very supportive message when Kimberly was nominated for the Ambassadorship, saying he was "so proud" of her and that she would be an "amazing leader." They still share a $9.7 million mansion in Jupiter, Florida (though they don't live there together anymore), and they haven't put it on the market yet.
It’s more of a business-like dissolution than a Hollywood divorce. They spent years building the MAGA brand together, and they both seem to realize that trashing each other would only hurt the movement.
A Quick Timeline of the Shift:
- 2018: Don Jr. and Kimberly start dating after his split from Vanessa Trump.
- 2020: They get engaged on New Year’s Eve (though they keep it secret for a year).
- 2024: The relationship hits the rocks; Don Jr. is seen with Bettina Anderson.
- September 2025: Kimberly is confirmed as Ambassador to Greece.
- December 2025: Don Jr. and Bettina Anderson announce their engagement at the White House.
- January 2026: Kimberly speaks out for the first time, wishing the couple well but remaining skeptical.
What's Next for the Former Couple?
Kimberly is likely to stay in Greece for the foreseeable future. She’s currently residing in the Jefferson House (the official ambassador’s residence) and is heavily involved in energy deals in the Ionian Sea. She’s effectively traded the campaign trail for the diplomatic corps.
Don Jr. is focused on his new life in Palm Beach with Bettina. He’s essentially moved into her townhouse, and a 2026 wedding is almost certainly on the horizon.
If you're following this story for the drama, the "actionable" takeaway is simple: watch the property records. When that Jupiter mansion finally hits the market, that’s when the very last tie between Donald Trump Jr. and Kimberly Guilfoyle will finally be severed. Until then, they remain weirdly connected by real estate and a shared political history.
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If you're interested in the business side, keep an eye on 1789 Capital. Don Jr.'s pivot from "campaign surrogate" to "defense tech investor" is where his real power is being built right now.