It finally happened. After months of side-eyes at Mar-a-Lago and whispers that the MAGA "power couple" was running on fumes, Donald Trump Jr. confirms he’s broken up with Kimberly Guilfoyle.
Honestly, the signs were there. For anyone paying attention to the Palm Beach social circuit over the last year, the vibe shifted from "unstoppable political duo" to "roommates who share a donor list." Don Jr. has officially moved on, recently becoming engaged to socialite Bettina Anderson, while Kimberly has packed her bags for Athens.
The Quiet End of a Four-Year Engagement
They didn't go out with a bang. It was more like a slow leak.
Don Jr. and Kimberly got engaged on New Year’s Eve back in 2020. They were the fire and brimstone of the Trump campaign trail. But by late 2024, the public bickering became hard to ignore. Insiders told Page Six that the two were frequently seen "getting argumentative" in front of guests at Mar-a-Lago.
Basically, the spark was gone.
By the time President Trump nominated Guilfoyle to be the U.S. Ambassador to Greece in December 2024, the relationship was effectively over. It’s a classic political move, right? If you can’t make the marriage work, a prestigious diplomatic post 5,000 miles away is a pretty good consolation prize.
What Don Jr. Actually Said
Don Jr. didn't pull a "we're over" Instagram post immediately. Instead, he took a more measured—almost professional—approach.
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In a statement given to Page Six, Don Jr. noted that he and Kimberly will "never stop caring for each other." He went on to say they will always keep a "special bond." He even defended her against critics, calling her an "undefeated prosecutor" and a "star."
It’s the kind of statement you write when you still have to work together. Or when your dad is the boss of both of you.
Enter Bettina Anderson
The real confirmation didn't come from a press release; it came from a ring.
While Kimberly was prepping for her Senate confirmation hearings for the ambassadorship, Don Jr. was already being spotted around Palm Beach with Bettina Anderson. She’s a 38-year-old socialite and former model who reportedly fits the "Trump mold" a bit more closely than the high-energy Guilfoyle did.
By December 2025, Donald Trump himself let the cat out of the bag. During a White House Christmas reception, the President announced his son’s engagement to Bettina.
"I’m at a loss for words," Don Jr. said at the podium during that event. "I get to marry the love of my life."
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Ouch. That’s gotta sting a little if you’re Kimberly, who was still technically co-owning a $9.7 million mansion in Jupiter, Florida, with him at the time.
Why the Split Happened Now
Relationships in this orbit are complicated. You’ve got politics, family brand, and massive real estate assets all tangled up together.
- The Style Clash: Sources close to the family suggested Don Jr. grew tired of Kimberly’s "always-on" persona. While she was a MAGA firebrand, he allegedly preferred the more "relaxed, Waspy" vibe that Bettina Anderson brought to the table.
- The Ambassadorship: Some see the Greece appointment as a "golden parachute." It allowed Kimberly to exit the immediate family circle with her dignity intact and a massive career win.
- The Father Factor: It’s no secret Don Jr. cares about his father’s approval. Reports indicated that the President "warmed up" to Bettina quickly, appreciating her more low-key, model-esque aesthetic.
Kimberly’s Take from Athens
So, how is the new Ambassador to Greece taking all this?
She’s being a pro. In a January 2026 interview with The New York Times, Kimberly finally broke her silence. She said, "I’m happy for Don. I wish him, of course, all the best."
Short. Sweet. A little bit frosty? Maybe.
But she’s busy. She’s currently living in the Jefferson House in Athens, the official ambassadorial residence. She even joked to Greek officials that she might be looking for a "new husband" soon. She’s moving on in her own way.
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What This Means for the Trump Brand
The "Don and Kim" era is officially in the rearview mirror. For years, they were the loudest voices at the rallies. Now, the dynamic has shifted.
Bettina Anderson is a much more private figure. She isn't a former Fox News host. She isn't shouting into microphones about the "best is yet to come." This suggests Don Jr. might be looking for a slightly different lifestyle as he moves into this next chapter of his life—one that’s perhaps a bit more Palm Beach and a bit less campaign bus.
The Real Estate Tangle
Interestingly, the break-up isn't entirely "clean" yet. Property records show that Don Jr. and Kimberly still both have their names on that $9.7 million Jupiter home.
Don Jr. has reportedly moved into Bettina’s townhouse in Palm Beach—his car is apparently there "always"—but the legalities of the shared mansion still need to be ironed out. It’s one thing to say you have a "special bond," and another thing to figure out who gets the equity in a nine-figure Florida estate.
What to Watch for Next
If you're following this saga, the next few months will be telling. Watch for:
- The Jupiter House Sale: Keep an eye on Florida real estate listings. When that $9.7 million mansion hits the market, you’ll know the final legal ties are being cut.
- Wedding Bells: With a White House announcement already in the books, a wedding between Don Jr. and Bettina Anderson is likely on the horizon for 2026.
- Kimberly’s Diplomatic Moves: As Ambassador, Guilfoyle is now a major player on the international stage. Expect her to focus heavily on U.S.-Greece relations to solidify her own legacy outside of the Trump family.
Actionable Insight: If you’re interested in the intersection of celebrity and politics, follow the official social media accounts of the U.S. Embassy in Greece. It’s the best way to see how Kimberly is rebranding herself as a high-level diplomat, completely independent of her former fiancé.