The Uncomfortable Gavin Newsom Joke Trump Once Made At Kimberly Guilfoyle's Expense
Sometimes, getting razzed by your partner's family is a harmless, lighthearted way for them to show you they consider you family — so much so that they're willing to tease you a bit to keep you on your toes. But when that razzing happens in front of a large audience, things can get a lot less endearing and a whole lot more awkward, as was the case with a tense joke former President Donald Trump made at Kimberly Guilfoyle's expense in 2018.
The ex-POTUS made the joke at a Washington, D.C., fundraiser in late fall of that year, looping Guilfoyle, who had just recently started dating his eldest son, Donald Trump Jr., in on the conversation when it veered off into Californian politics. Discussing West Coast immigration policies and various California politicians who have had choice words about Trump, the former president brought up the future California governor, Gavin Newsom.
"Kimberly, you know him, right?" Trump said, as reported in Anna Palmer and Jake Sherman's book "The Hill to Die On." As the authors put it, "There was some awkward, tepid laughter around the room." Awkward and tepid indeed — Trump had not so subtly brought up the fact that Guilfoyle was once married to Newsom from 2001 to 2006.
The awkward exchange seemed to hint at tensions between Guilfoyle and the Trumps
While not all members of the Trump family are as forthcoming with their opinions about others as its patriarch, former President Donald Trump, rumors have swirled around the media about how the Trumps really feel about Kimberly Guilfoyle ever since she and Donald Trump Jr. became an official item. A few years after the ex-POTUS publicly referenced Guilfoyle's former marriage to California Governor Gavin Newsom, political insiders claimed the lawyer and Fox News personality had yet again peeved Donald Trump.
In 2021, Guilfoyle agreed to serve as the national campaign chair for disgraced politician Eric Greitens, who was running for Missouri Senate. Greitens, who came under fire for both blackmail and domestic violence, was not on Donald Trump's good side. Unfortunately for Guilfoyle, some of that disdain transferred over to her by proxy. "Trump thinks Greitens is problematic and that Kim is annoying," an anonymous Trump advisor told Politico in 2021.
At the time these comments were published, Guilfoyle had already been engaged to Trump Jr. for about a year. But according to some reports, not even an engagement was enough to soften the Trump family's opinions about Guilfoyle. According to an unnamed source who spoke to OK!, "Ivanka [Trump] doesn't trust her because she sees her as a social climber desperate to marry into the family." Not a great vote of confidence from one's future sister-in-law.
Guilfoyle's relationship with the Trumps seems to have improved (for some relatives, anyway)
While those comments about the Trump family's opinions about Kimberly Guilfoyle seem damning, Donald Trump's appearance at Guilfoyle's lavish 54th birthday party in March 2023 seem to suggest that his feelings toward her have softened. According to an insider who spoke to Page Six, "Trump gave a big, long speech praising Kimberly and saying, 'I look forward to officially welcoming Kimberly into the family when Don [Jr.] marries her. We all love her.'"
The former president went on to thank Guilfoyle for her help with his political campaigning, adding, "She and Don are a wonderful couple." Guilfoyle's future sister-in-law, Ivanka Trump, and her husband, Jared Kushner, were invited to the event but declined due to their niece's bat mitzvah that had been planned before the birthday party. Regardless of what the rest of the Trump family thinks about Guilfoyle, it's clear that Don Jr. doesn't care about naysayers.
In a somewhat awkward tribute to Kimberly Guilfoyle, Don Jr. posted a photoset of him and his fiancée with the caption, "Happy 6 year anniversary [Kimberly] thanks for always being there no matter what the haters are throwing our way. I love you." Is it weird to mention critics in a six-year anniversary post with your future wife? Maybe! But it's arguably no less awkward than bringing up someone's ex-husband at a political fundraising event like Don Sr., so maybe bad timing just runs in the family.