Donald Trump & Kimberly Guilfoyle's Relationship Is Reportedly More Complicated Than We Knew

Kimberly Guilfoyle has been on the campaign trail stumping and Trumping like the best of them. She's such a fierce supporter that if you cut Guilfoyle, she would bleed Trump. Still, when it comes to Guilfoyle's personal relationship with Donald Trump, things are, well, a lot more...complicated.

Despite whispers to the contrary on unsubstantiated forums like Reddit, there seems to be no doubt about Guilfoyle and Donald Trump Jr.'s relationship, which is going gangbusters by all accounts. However, it's all a bit more convoluted regarding Don Jr.'s dad. Guilfoyle purportedly fell massively from favor in July 2021 when she signed up to work on disgraced governor Eric Greitens' campaign to replace incumbent Roy Blunt's Missouri Senate seat, somebody who definitely wasn't on Donald's good books. "Trump thinks Greitens is problematic and that Kim is annoying," a Trump adviser told Politico. "He said, 'Why the f*** is she working for him?'"

Ironically, some believe that some of Donald's issues against Greitens included the fact he was forced to step down as Governor of Missouri following multiple accusations of sexual misconduct, extramarital affairs, shady financial shenanigans, and his close ties to VP Mike Pence. Meanwhile, Donald's main issue against Guilfoyle — aside from her working for somebody he hadn't given his stamp of approval to — was the belief it would signal his endorsement of Greitens, given her relationship with Don Jr. Ultimately, Greitens was trounced by Republican Missouri Attorney General Eric Schmitt. But that didn't mean Guilfoyle was immediately back in Donald's favor.

Donald was reportedly unhappy Don Jr. started dating Guilfoyle

It definitely seems Donald Trump and Kimberly Guilfoyle's relationship is more complex than suspected. Even before the reported fallout between Donald and Guilfoyle over stumping for Eric Greitens, there had been rumors that something was rotten in the state of Trumpland. In October 2019, The Atlantic reported that 45 was peeved about Donald Trump Jr. dating Guilfoyle.

That was clear when Donald refused her attempts to become White House press secretary. "Even he can tell the difference between the attractive women on Fox who have a little bit of substance and those who will be derided as airheads," an aide said. "Now she was gallivanting across the gossip pages with his son and posing for photos on the South Lawn." Meanwhile, two Trump associates said Donald made it clear Guilfoyle would not be sitting at the table for the big Trump Turkey Day festivities — a claim flatly denied by Don Jr. and a White House spokesperson.

Then, there's how Don Jr.'s siblings reportedly feel about Guilfoyle, specifically Ivanka Trump. A hoo-ha was created in November 2022 when Ivanka chopped an all-black-clad Guilfoyle out of an Instagram Story photo (via Newsweek) from Tiffany Trump's wedding. "Ivanka loves Kimberly and in no way would crop her out," a friend insisted to the Daily Mail. "The two women are very close, and Kimberly has really become part of the Trump family. When Ivanka realized what had happened, she immediately reposted the photo."

Guilfoyle's leaked texts help criminal case against Donald

Ivanka Trump reposted the "accidentally" edited photo from Tiffany Trump's wedding that cut out Kimberly Guilfoyle from the picture. However, she only reposted it to her Instagram Story, where the content disappeared after 24 hours; the original edited version remains on her Instagram feed. So, make of that what you will. And, if you scroll through the feed, there's a distinct lack of Guilfoyle photos. Lara Trump crops up regularly. But when it comes to the occasional Guilfoyle photo, she's either lurking somewhere in the background, barely visible, or relegated to the sidelines.

Donald Trump and Guilfoyle's relationship likely became much more complicated after a bunch of her texts were leaked in January 2022. It's safe to say this didn't go down well with or look good for her future father-in-law. Pro Publica saw the texts, which included Guilfoyle gloating to Katrina Pierson, White House event liaison, that she'd "raised $3 million for the rally that helped fuel the Jan. 6 Capitol riot." This added fuel to the prosecution's criminal case that the Trump inner sanctum was directly linked, financially and organizationally, to the Capitol attack.

Still, don't despair, Guilfoyle fans! Eric Trump shot down the reports of a rift between the family and the former Fox News host, insisting that everybody loves her. "I completely disagree with the narrative and happen to think the world of Kimberly," Eric told Page Six in December 2022, also insisting he's "best friends with Don."