Kimberly Guilfoyle has moved to Athens for her new role as the U.S. ambassador to Greece, but her Instagram is still in Mar-a-Lago. On October 12, she celebrated Lara Trump’s birthday with a post. Except it ended up looking more like a scrapbook of her life with Donald Trump Jr. The ambassador posted a nine-photo Instagram Story collage for Lara Trump, wife of Don Jr.’s brother, Eric. But half the pics included Don Jr., and the others had been taken at events where he was lurking just outside the frame. It was less “Happy Birthday, Lara!” and more “Hey everyone, remember when I was basically the First Lady of Trumpworld?”
Kimberly Guilfoyle tagged both Eric and Don Jr. It came across as part reunion wish, part power play. She could have chosen a picture with Lara. Instead, she picked nine to make sure no one forgot she once had a spot in the group text. It’s been a dizzying few years for Guilfoyle. Once a Fox News mainstay and rumored contender for White House press secretary, she reinvented herself as a political fundraiser and later as one of President Donald Trump’s defenders. Her 2020 Republican National Convention speech made her a MAGA meme.
Fast forward to 2025, and Guilfoyle’s life looks different…at least on paper. Kimberly Guilfoyle is now Ambassador to Greece, confirmed by the Senate in September after staying loyal to Trumpworld. Yet despite the title, her social media tells that she clings to her past relationship with Don Jr. Before her Lara Trump post, Guilfoyle shared a birthday tribute to her 19-year-old son, Ronan Villency. Most of the slideshow featured her, not him. Dressed in gowns and rally outfits, Guilfoyle is more interested in her image than in celebrating her son.
Trump has hired Don Jr’s girlfriend Kimberly Guilfoyle as his Senior Campaign Advisor, insisting, “She’s as stupid, narcissistic, greedy and corrupt as if she was my own child” pic.twitter.com/KOEZSwIlO9
— Paul Rudnick (@PaulRudnickNY) April 30, 2019
But the Lara Trump tribute was a new level of self-reference. As Trumpworld moves on (Don Jr. is now with socialite Bettina Anderson, who posts beach pics with Ivanka), Guilfoyle curates her feed as a highlight reel from a relationship that ended a year ago. Don Jr. reportedly ended his engagement with Guilfoyle after nearly five years, and insiders say the family has welcomed his new partner, unlike Guilfoyle, who never quite achieved it. While she mingled with the Trumps at official events, Anderson is now part of their personal circle as she hosts a Labor Day getaway with Ivanka and her kids in The Exumas. Ivanka gushed about “special memories made in paradise,” and that looks like a pretty clear sign that Anderson replaced Guilfoyle as the Trump family’s plus-one.
Meanwhile, Kimberly Guilfoyle tries to reconnect through social media, but it seems one-sided. None of the Trumps have “liked” her posts, not even the one celebrating her swearing-in. The only family member who acknowledged that milestone was Tiffany Trump. It’s a strange chapter for someone once seen as a rising power in conservative politics. Her ambassador role could’ve been a fresh start, but her Instagram suggests she’s still orbiting her ex’s world. It’s almost like a scene out of The First Wives Club.
With Ivanka Trump’s birthday coming on October 30, will Guilfoyle post another memory featuring Don Jr., or will she post something that screams “Madame Ambassador” instead of “MAGA ex”? Either way, her Instagram remains a quest for validation!
NEXT UP: Kimberly Guilfoyle and Lauren Sánchez Have More in Common Than You Think
