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What a Crop
Optics-Obsessed Ivanka Claims "My Bad," But Kimberly Guilfoyle Remains on the Fringe of the Trump Clan
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“A picture is worth a thousand words” goes the adage.
And never was that truer than with the picture Ivanka Trump posted to commemorate her half-sister Tiffany Trump’s wedding this weekend. In the photo are five statuesque blondes who were all, other than the bride, dressed in flowing, pastel-colored or light metallic dresses. Just one thing was missing: Don Jr.’s fiancé Kimberly Guilfoyle, 53, who had been dressed in black, and who Ivanka had cropped out of the photo.
The wedding photo as originally posted to Ivanka Trump’s Instagram account.
Though she later posted the photo in its entirety to her Instagram Stories with three “smiling face with hearts” emojis, Ivanka’s initial omission highlighted what my sources report as “tensions” between the former president’s eldest daughter and Guilfoyle, whose colorful dating life pre-Don Jr. is said to be one of the major causes of a long-held mistrust between the two women.
The uncropped image that was later posted to Trump’s Instagram Stories.
“It was well known that Ivanka was not a fan of Kim,” someone who knows both women well told me.
Following her second marriage to furniture designer Eric Villency and prior to her relationship with Don Jr., Guilfoyle was seen as a trophy among the Republican men, many of whom competed for a date, multiple sources told me.
Sources also told me that Guilfoyle is much warmer and funnier in person than she looks in photographs (at least the ones that she’s not cropped out of) and a lot lighter than the didactic screamer she presented as in her speech to the Republican National Convention in August 2020.
And back in July 2017 when I was reporting on a dinner in DC attended by Guilfoyle, Donald and Melania Trump, and Anthony Scaramucci (who was secretly separated from his wife at the time—they since reconciled), Roger Stone phoned me during my reporting to tell me that I shouldn’t write anything suggesting that Guilfoyle and Scaramucci were getting close (they are friends and always denied any relationship). Stone told me: “Kimberly is very attractive. She’s there because the president would date her if he could.”
None of that explains, however, why Guilfoyle decided to wear a black cocktail dress to Tiffany Trump’s black-tie wedding in Florida.
Admittedly I grew up in the UK, where people are extremely fussy about what is appropriate and what not (the Brits invented Royal Ascot, with all its stringent dress codes after all), and I know that the notion that black and white are the two colors that are absolutely verboten at a wedding is now considered outdated this side of the Atlantic (although I am yet to see a white dress on anyone other than the bride). Nonetheless, if the Trump women were close, a conversation about Tiffany’s wedding would surely have included questions about what everyone was wearing. To this day, my girlfriends and I ask each other what we are each wearing to special events, to make sure we’ve got the tone right. Sometimes business casual is anything but casual, and “black tie” isn’t always full-on, long-dress black tie…
But it would seem no one involved Guilfoyle in a conversation like that. Or they did and she didn’t care (in which case, points for her!).
Nonetheless, all this frivolous speculation does raise the question: Just how are the Trump family dynamics going to play out after Trump announces tomorrow he’s running for president, as he surely will?
Lara Trump was on Fox News this Sunday, basically telling Ron DeSantis to back off and wait his turn in 2028.
My sources tell me that Lara intends to run for office one day. Don Jr. might too, but only when his kids are older, though he has no intention of going into the White House or government if his father were to win a presidential election in 2024. Don Jr. has got his own business to run. He has a book publishing company—and a hunting company, apparently. Branding is in the genes, it would seem.
As for the Kushners? They will not be gracing DC again with their presence. They are now focused on becoming gazillionaires.
So what does that mean for Guilfoyle? Given her legal training, her first marriage to Gavin Newsom when he was San Francisco mayor, and her long stint on Fox News, she has arguably more knowledge and political experience than her future husband and siblings-in-law put together. But I’m told she has no intention of running for anything. My question is: Why not?
There was something sad about the two photographs Ivanka posted—the one without Kimberly and then the one with her in it. Maybe I’m hallucinating, but to me she seems the odd one out—shorter, dressed differently, and, as of now, strangely silent for someone who has had a very public voice for many years.
It does make you wonder: What is really going on within the Trump dynasty? And what will the repercussions be once Trump announces? I guess we shall have to just wait and see…