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.”
