It happened in the middle of a White House Christmas party. Not exactly the place you expect a breakup post-mortem, but that’s the Trump era for you. On December 15, 2025, Donald Trump Jr. stood up and basically told the world he was moving on. He announced his engagement to Bettina Anderson, a Palm Beach socialite. The room cheered. His dad hugged him.
But wait. What about Kimberly?
If you’ve followed the MAGA power couple over the last few years, the split felt like a slow-motion car crash that finally hit the wall. They were the fire and ice of the campaign trail. Kimberly Guilfoyle, with her "The best is yet to come!" roar, and Don Jr., the outdoorsy, crypto-pushing heir apparent. They were engaged for nearly four years. Then, suddenly, they weren't.
The Quiet End of an Era
People keep asking when it officially ended. Honestly, it's complicated. They didn't put out a glossy "we've decided to go our separate ways" Instagram post right away. Instead, it was a trail of breadcrumbs.
Rumors started swirling late in 2024. Don Jr. was spotted in Palm Beach holding hands with Bettina Anderson while most people still thought he was headed for the altar with Kimberly. It was awkward. Very awkward. Sources eventually told the New York Post and People that the two had quietly split before he moved on, but property records tell a different story of a messy "untangling."
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They still co-own a $9.7 million mansion in Jupiter, Florida. You don't just walk away from a house like that overnight.
While Don Jr. was essentially moving into Bettina’s Palm Beach townhouse—his car was reportedly parked there 24/7—Kimberly was preparing for a massive career pivot. In late 2024, the President-elect nominated her to be the U.S. Ambassador to Greece. Some called it a promotion; others called it a "golden parachute" to get her out of the immediate family circle.
Life in Athens vs. Life in Palm Beach
By November 2025, the split was as official as it gets. Kimberly packed her bags and moved to Jefferson House, the official ambassadorial residence in Athens.
She seems to be thriving, or at least she’s putting on a world-class show of it. A recent New York Times profile labeled her the "talk of Athens." She’s doing diplomatic things, hosting events, and—in classic Kimberly fashion—already making headlines for clashing with the Chinese embassy over port control.
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When asked about Don Jr.’s new engagement in early January 2026, she kept it professional. "I’m happy for Don," she told the Times. "I wish him, of course, all the best."
Underneath that poise, though, insiders claim there’s still some tension. It’s hard to watch your ex-fiancé get engaged to someone else at your former future-father-in-law's house. Especially when that engagement comes only a year after you were still living together.
The New Players
- Bettina Anderson: The new fiancée. She’s a fixture in the Palm Beach social scene. Unlike Kimberly’s high-octane political persona, Bettina is described as a "natural fit" for Don’s current lifestyle.
- The Family Vote: President Trump has reportedly given his blessing, with sources saying he’s "happy with the way Bettina looks" and wants his son to be "satisfied."
- The Ex-Factor: Interestingly, Don Jr.’s first wife, Vanessa Trump, has also moved on—she’s been linked to Tiger Woods. The Trump family tree is getting very crowded.
Why the Breakup Still Matters
This wasn't just a celebrity split. It was a business and political divorce. Kimberly wasn't just the girlfriend; she was a top-tier fundraiser and a fixture at the RNC.
There were reports that some in the Trump inner circle felt she was becoming a "grandstander," trying to pull too much of the spotlight toward herself. In politics, that's a dangerous game to play when your last name isn't actually on the ballot yet.
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Now, the power dynamic has shifted. Don Jr. is leaning into new ventures—crypto mining, a partnership with 1789 Capital, and investing in the "Enhanced Games" (the ones that allow performance-enhancing drugs). He’s building his own brand, separate from the "power couple" image he shared with Kimberly.
What’s Next for Kimberly and Don Jr.?
If you’re looking for a reconciliation, don’t hold your breath.
Don Jr. is full steam ahead with wedding planning in Palm Beach. Kimberly is busy navigating the geopolitical waters of the Mediterranean. They still have to deal with that $9.7 million house, which remains in both their names as of early 2026. Real estate is usually the last thing to settle in a breakup of this scale.
Actionable Insights for Following the Story:
- Watch the Property Records: Keep an eye on the Jupiter, FL property filings. When that mansion sells or one name is removed, the final legal tie between them is officially severed.
- Monitor the Embassy Cables: Kimberly’s tenure in Greece is likely to be loud. If you want to see if she still has "MAGA" influence, watch how much the State Department allows her to deviate from standard diplomatic script.
- Follow the 1789 Capital Moves: Don Jr.’s financial independence is his new focus. His success here will determine if he remains a power player in his own right or stays strictly in his father's shadow.
The "Kimberly and Don" chapter of the Trump dynasty appears to be closed, but in this circle, nobody stays out of the headlines for long.