Kai Trump, Donald Trump’s 17-year-old granddaughter, has emerged as the leading voice in the young, up-and-coming generation of America’s new ruling dynasty, and she’s been giving off major signals as to who’s in and who’s out in the family’s inner circle.
The oldest daughter of Donald Trump Jr., who also is an aspiring college golfer and social media influencer, has been busy sharing family photos and videos ever since her grandfather’s stunning Nov. 5 victory over Kamala Harris.
Judging from these family images, the No. 1 person who may be “down and out” in the Trump family circle is Kimberly Guilfoyle, her father’s long-time fiancee, the Daily Beast reported. Meanwhile, Kai Trump has let it be known that billionaire Elon Musk, who reportedly pumped some $130 million into her grandfather’s successful re-election campaign, has achieved “uncle status.”
On social media this week, Guilfoyle continued to promote herself as a fervent Trump loyalist and shared a video of Trump Jr. giving a celebratory, post-election interview on Fox News. But for weeks, the 55-year-old Guilfoyle has faced speculation that her relationship with Trump Jr., 46, is troubled, following reports in September about his alleged “dalliance” with another, younger woman, the Daily Beast also reported.
Trump family observers noted a distance between Guilfoyle and Trump Jr. on election night, when he was seen trying to avoid standing next to her, as they joined the rest of the family and other top Trump supporters on stage in Florida to celebrate their patriarch’s return to the White House.
In a video, Trump Jr. can be seen switching his location away from Guilfoyle several times before finally settling on turning his back to her, the Daily Beast reported. But Trump Jr. wasn’t the only person who may have been trying to avoid Guilfoyle, according to another Daily Beast report. She also seemed to be getting “major side-eye” from Kai Trump, who is one of five children that Trump Jr. shares with his ex-wife, Vanessa Trump.
Such tension doesn’t bode well for Guilfoyle, according to the Daily Beast. If Gulfoyle “hasn’t won her would-be stepdaughter over, it could be an uphill battle for her future as Mrs. Don Jr.,” the Daily Beast said.
Two days later, Kai Trump posted a curious family photo on X — that didn’t include Guilfoyle. The photo was taken at Mar-a-Lago on election night, and the teenager captioned it “the whole squad.” The photo showed the future 47th president surrounded by all five of his adult children and three of their partners, along with Kai and her four siblings.
But Guilfoyle was notably absent from the “squad” photo. More or less in her place was Vanessa Trump, who stood with her ex-husband and their five children.
Melania Trump also was missing from the photo — and probably for reasons that could take a while to unpack. However, “Uncle” Elon Musk was prominently featured in the photo, standing off to the side with his adored 4-year-old son, X-AE-A12.
On Sunday, Kai Trump shared more behind-the-scenes images from election night that didn’t include Guilfoyle. On YouTube, she posted an election-night video that included scenes of an elegant living room in her grandfather’s Mar-a-Lago resort in Palm Beach, Florida where the family had gathered to watch election night coverage. At one point, the video showed Kai standing with her father and mother, while Trump sat at a table. Barron Trump also stood in the frame.
Other video clips showed the family getting together to pose for the “squad” photo with Trump. There was an initial photo of the 45th president posing with Trump Jr. and his family, including Vanessa, Kai and their four other children. For this photo, the former real estate mogul and reality TV star insisted that Musk and his “beautiful” son join in this group shot.
Pretty soon, other family members gathered for another group photo, including Barron, Tiffany and her husband, Michael Boulos, Ivanka Trump and Jared Kushner and Eric and Lara Trump. Musk and his son also were included, but once again, there was no sign of Guilfoyle and Melania Trump.
As for Musk, Kai Trump shared a photo of herself with the Tesla CEO on Sunday. It showed her standing on a golf course with the X founder and his son, who is one of his 11 children. She captioned it, “Elon achieving uncle status,” with a laughing emoji.
But the status of Trump Jr.’s relationship with Guilfoyle remains a mystery, even as a NewsNation report said last month that their relationship is “doing fine.” The former San Francisco prosecutor and early nemesis of Vice President Harris was a major fundraiser for Trump — and the president-elect thanked her in his victory speech at the West Palm Beach Convention Center.
Guilfoyle, who also is the ex-wife of California Gov. Gavin Newsom, began to show her Republican leanings after she left California in 2004 to pursue a career as a legal commentator on cable news. Her conservative views appeared to harden as she joined Fox News, and she became a full-blown MAGA supporter when she and Trump Jr. began dating in 2018.
They became a MAGA power couple as they bought a house together in Florida and campaigned for Trump in 2020. Guilfoyle’s passion for “all things Trump and Don Jr.” became a large part of her public persona, the Daily Beast said.
But in September, the pro-Trump Daily Mail reported that Guilfoyle had been “blindsided” by revelations that her fiance has been “fooling around” with another woman, a pretty blonde Palm Beach socialite named Bettina Anderson. Also potentially troubling for Guilfoyle: This “dalliance” had become an “open secret” in elite Republican circles in and around ritzy Palm Beach, the Daily Mail also said.
“Kimberly either didn’t know about Bettina — or didn’t want to know,” an insider told The Daily Mail in September. “Did she hear whispers that Don Jr. was fooling around with someone else? Probably.”
Moreover, Anderson appears to be friendly with both Vanessa and Kai Trump. Social media photos posted online show Anderson and the mother and daughter hanging out at an “intimate” gathering of Trump supporters in Florida sometime over the summer, the Daily Mail reported.
On the campaign trail in the weeks following the Daily Mail report, Trump Jr. and Guilfoyle “pressed on — often with strained-looking poses and awkward appearances together,” the Daily Beast also reported.
Political observers wondered if the relationship would survive past the election, following photographic evidence of him “canoodling” with the socialite, according to Puck writer Tara Palmeri on her podcast, “Somebody’s Gotta Win.”
Guilfoyle also has emerged as a rather “awkward brand of MAGA mistress,” the target of unflattering memes about her appearance and her habit of yelling through her speeches, the Daily Beast said.
It probably wouldn’t help Guilfoyle if she had gotten on the wrong side of Kai Trump, the Daily Beast also reported. For one thing, Kai has become a force in her grandfather’s political movement, especially after she spoke at the Republican National Convention and showed she had the power to appeal to other young voters and to “humanize” her “normal grandpa.”
On election night, Guilfoyle may have been the only woman in the world more somber than Harris — “and all the contouring in the world couldn’t hide it on her face,” the Daily Beast said. Trump Jr. seemed to make it clear that she was “the odd man out.”