Inside Donald Trump's Relationship With Don Jr.'s Fiancée, Kimberly Guilfoyle

Ever since Kimberly Guilfoyle began dating Donald Trump Jr. in 2018, she's been a staple of the conservative tabloid circuit. "They are like the prom king and queen of MAGA land," a Trump advisor joked to Business Insider. The former Fox News talking head is famed for her brash and outspoken persona, dishing up slices of MAGA hot takes with little encouragement. It comes as no surprise, then, that her partner's father, Donald Trump, gave her a prominent fundraising role during his ill-fated bid for reelection in 2020. His unsuccessful campaign didn't deter him, however, and both Don Jr. and Guilfoyle have made a return to the political limelight.

Following an assassination attempt on Donald Trump in July 2024, Guilfoyle once again came out in support of her future father-in-law, lauding his fortitude in a chat with Sky News. "He's very resilient," she said. "And we're just so proud of him and so grateful and we're blessed that he's okay. ... He's doing an amazing job and the American people love him." With the race for the White House between Donald Trump and Democratic hopeful Kamala Harris heating up, we may turn our attention to Guilfoyle's influence on her prospective father-in-law. Though Donald and Guilfoyle share many notable similarities, their relationship has been far from smooth sailing.

Though Donald Trump has a positive relationship with Jared Kushner, the husband of his daughter Ivanka Trump, his feelings towards Kimberly Guilfoyle are a little more complicated. Prior to getting with Guilfoyle, Donald Trump Jr. was married to Vanessa Trump, who filed for divorce in 2018. Struggling to warm to his eldest son and namesake's partners seems to be a recurring theme for the senior Trump. In 2019, The Atlantic reported that the 45th president never cared for Vanessa, which may have been due to her alleged past romantic association with a member of a street gang, or possibly her having called her father-in-law an ableist slur at a fashion show.

However, when his son found new love with Guilfoyle, Trump Sr. reportedly harbored even more animosity towards her. This was apparently spurred by the Fox host's bid to become his press secretary, with the then-president dismissing Guilfoyle as supposedly having inferior intellect and little substance. "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," a former aide told The Atlantic.

Moreover, there have been claims that Don Jr. and his father had both been vying for the affections of Guilfoyle. An advisor told the publication that at one point, the latter apparently made risqué remarks about Guilfoyle and tried to find out if she was single, despite being married to Melania Trump.

Speaking to Page Six in 2022, a source close to Eric revealed, "The vibe is that the [Trump] family doesn't like Kim. She is trying too hard to be in the family." When asked to comment, though, Eric explained, "I completely disagree with the narrative and happen to think the world of Kimberly," he said.

Nevertheless, speculation grew that Donald Trump was at odds with Guilfoyle after it was revealed that he made a fleeting appearance at her and Don Jr.'s Toys for Tots fundraiser, which was held at the couple's swanky abode. Trump Sr. reportedly lasted just a half-hour at the event, which notably wasn't attended by Ivanka Trump and her husband, Jared Kushner. While a source denied there was anything other than a scheduling conflict that prevented Ivanka and Kushner from attending, there have been rumors of a beef between the couple and Guilfoyle.

Sources alleged to New York Magazine's Intelligencer that Guilfoyle's appearance at the couple's Fourth of July party upstaged Ivanka and Kushner, and Don Jr. was subsequently asked to check before bringing a guest to later events. It was later claimed that Trump Sr. barred Guilfoyle from attending the family's Thanksgiving dinner at Mar-a-Lago, although White House press and Don Jr. denied this rumor.

There's no denying that Donald Trump has made a list of powerful enemies over the years. The former president's contentious persona has routinely drawn the wrath of former aides and friends, a number of whom decided to write books about their experiences with the Donald. It's in this fiery temperament that Trump and Kimberly Guilfoyle share some common ground. Following her departure from Fox News in 2018, Guilfoyle became a loud, brash, and opinionated figure on the MAGA circuit, giving rousing speeches and appealing to the populist vote. Sound familiar? "It's interesting to me that Donald Trump Jr. ended up with a female version of his father," Guilfoyle's former colleague told Business Insider.

Prior to getting with Guilfoyle, Don Jr. had long been stuck in his father' shadow. Trump Sr. was even hesitant to name his eldest son after him, as he reportedly feared that he could grow up to be a "loser." But thanks to apparent coaching by Guilfoyle, Don Jr. has become a prominent populist figure in his own right. Though Trump Sr. seemingly didn't want her as his press secretary, he did eventually give Guilfoyle a role as an advisor in his 2020 presidential campaign. It seemed, perhaps, that he was finally warming to Guilfoyle, a woman with whom he shares so many attributes.

Kimberly Guilfoyle's first marriage to governor Gavin Newsom ended in divorce. In 2006, a year after her split from Newsom, she wed furniture heir Eric Scot Villency. Three years later, this marriage also ended in divorce. Guilfoyle's relationship with Newsom has been a point of contention — Newsom is a Democrat and generally holds matching views. He has heavily attacked Republicans — as well as the right of the Democratic party — over their views on abortion, gun safety, and healthcare. This is, of course, in stark contrast to his ex-wife, who has been dubbed by some as an alt-right grifter. Notably, she was vocal in her support of the controversial overturning of Roe v. Wade in 2022, whereas Newsom has since approved legislation to make it easier for pregnant people to obtain abortions following the Supreme Court's ruling. 

Donald Trump has reportedly been amused by his future daughter-in-law's past romantic association with Newsom, using it as leverage to mock her. According to the book "The Hill to Die On" by Anna Palmer and Jake Sherman, Trump even made fun of Guilfoyle right to her face during a fundraiser in 2018. The president reportedly began ranting about Newsom and his liberal policies, quipping to Guilfoyle, "Kimberly, you know him, right?" (via People). Ouch. The awkwardness of the jibe was not lost on the guests. "There was some awkward, tepid laughter around the room," noted Palmer and Sherman.

As Donald Trump made his bid for reelection in 2020, it was revealed that he had been paying Kimberly Guilfoyle enormous sums of money via campaign donations. According to two anonymous GOP sources who spoke to the HuffPost, Guilfoyle, along with Eric Trump's wife, Lara Trump, was getting paid a handsome $15,000 a month via campaign manager Bradley Parscale. "I can pay them however I want to pay them," Parscale told the outlet.

Subsequently, some argued that Guilfoyle did not merit such a hefty pay packet, reiterating the aforementioned claims that Trump Sr. views her as little more than a Fox News airhead. "She's doing stuff, but she's just like this silly cheerleader," a White House advisor quipped. "She gets on these donor calls, and it's ridiculous."

Likewise, there was the question of ethics regarding funneling huge amounts of donor money to Trump Sr.'s partners. "A lot of people close to Donald Trump are getting rich off of his campaign," said Paul Ryan, then-vice president for policy and litigation at the government accountability watchdog Common Cause. "They don't want donors to know that they're getting rich. Because, at the end of the day, it's donor money." In addition to her monthly salary, Guilfoyle was getting paid tens of thousands of dollars to make pithy speeches at Trump rallies, leading to further controversy over the misuse of donor funds, USA Today reported.

In 2021, Kimberly Guilfoyle began working with former Missouri governor Eric Greitens during his bid for the senate. "[Guilfoyle's] work on behalf of President Donald J. Trump was unmatched," Greitens said (via Politico). "We know the Democrats will come after this campaign, just like they came after President Trump. With Kimberly Guilfoyle as our National Chair, I know we have a true fighter that will further elevate this campaign."

This reportedly drew the ire of Donald Trump, who disapproved of Greitens due to allegations that claimed the governor had violently sexually assaulted a woman with whom he was having an extramarital affair. According to aides, Trump, who has himself been accused of sexual misconduct by multiple women, couldn't fathom why his future daughter-in-law would associate with a figure as divisive and unsavory as Greitens. 

"Trump thinks Greitens is problematic, and that Kim is annoying," a Trump advisor told Politico. "He said, 'Why the f*** is she working for him?'" Accordingly, Trump allegedly feared that Guilfoyle's partnership with Greitens might make it seem like he himself was endorsing the controversial politician — fears that were no doubt exacerbated by Greitens comparing his senate bid to the Trump campaign in the aforementioned statement. However, Guilfoyle denied the story.

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Donald Trump may have ambivalent feelings towards Kimberly Guilfoyle, but she sure loves to sing her prospective father-in-law's praises. In 2020, she made headlines following an infamously loud speech at the Republican National Convention, in which she endorsed Trump for president in a manner that might best be described as unhinged.

"President Trump is the leader who will rebuild the promise of America," Guilfoyle said (via People). "We build things up, we don't burn them down. We kneel in prayer and we stand for our flag." Was the latter remark a dogwhistle directed at NFL players, who took the knee during the national anthem in protest of police brutality against Black people? It's entirely possible, as Guilfoyle derided Colin Kaepernick multiple times previously. Trump also heavily criticized NFL stars who took the knee, decrying them as unpatriotic and suggesting that they should leave the country. This seems to be another shared sentiment between Trump Sr. and Guilfoyle.

On his eponymous "Late Show," Stephen Colbert mocked Guilfoyle over her speech, declaring her the "Trump Jr. girlfriend and vengeful banshee who will haunt your dreams." As the years went on, the similarities between Guilfoyle and Trump became ever more apparent. On an episode of her show in 2023, Guilfoyle sounded suspiciously like the self-aggrandizing Trump as she waxed lyrical about his supposed positive attributes. "He has unbeatable stamina," she gushed (via X). "And that's what we need in a leader. Not to mention his golf game when he hits, like, holes-in-one, I've seen it personally, okay?"

Following the violent Capitol riots, there was a major backlash against the Trump brand. On January 6, 2021, some Trump supporters, believing that the election was "stolen," stormed the Capitol building to protest the presidential victory of Joe Biden, during which five people died. Trump has long been accused of inciting the violence that took place. On the day of the riots, he held a Save America rally, in which he called his supporters to action. "We want to go back, and we want to get this right because we're going to have somebody in there that should not be in there and our country will be destroyed, and we're not going to stand for that," he said, per the Associated Press.

In November 2021, ProPublica alleged that Kimberly Guilfoyle had bragged about raising $3 million for the Save America rally and attempted to arrange for far-right speakers to appear alongside Trump. She was also hoping to speak at the rally herself, but that didn't quite go as planned. When then Trump aide Katrina Pierson told Guilfoyle via text message that the former president had arranged all the speakers himself, Guilfoyle stated that she wanted to be the one to introduce her fiancé, Donald Trump Jr. "[I] raised so much money for this," she lamented in the text. "Literally one of my donors Julie at 3 million." Guilfoyle denied allegations that she raised funds for the rally.

Over the years, Donald Trump has seemingly grown closer to Kimberly Guilfoyle. In 2023, the former Fox host held a 54th birthday in Jupiter, Florida, and Trump made the surprise decision to show up. Those in the know noted that it was an unusual move. "The crowd was not celeb-studded . . . Trump rarely leaves Mar-a-Lago, so it was unusual to see him out in Jupiter . . . He arrived at 8 p.m. and left before 10 p.m," an insider told Page Six. "The crowd looked like some neighbors and a lot of potential donors. There were no tickets, but it felt like Kimberly would be calling the guests later for contributions."

In yet another surprising moment for Trump, he was spotted dancing vigorously at the party, before giving a long speech in which he praised Guilfoyle. "I look forward to officially welcoming Kimberly into the family when Don [Jr.] marries her . . . we all love her. ... She's a terrific addition to the campaign and she and Don are a wonderful couple," he allegedly said. Of course, this is in marked contrast to what insiders claimed Trump was saying about Guilfoyle just a few years earlier. The Donald may have been growing closer to his son's fiancée, but some wondered if tensions between Guilfoyle and other members of the Trump clan persisted. Ivanka Trump and Jared Kushner, for instance, were notably absent from the party despite being invited, although a source told the publication that this was due a previous commitment. 

As Donald Trump returned to the limelight following an assassination attempt in July 2024, so did his hangers-on. Cementing her support for Trump, Kimberly Guilfoyle gave a rousing speech at the Republican National Convention days after the attempt on the would-be president's life. In what was characterized as an "unhinged" speech that entailed a lot of yelling, Guilfoyle seemingly did her best Trump impression while lauding her future father-in-law in Milwaukee. "I know personally what every American has now seen with their own eyes!" she yelled (via The Independent). "I know the measure of the man that stands before us, Donald Trump will never stop fighting for you. Join me in voting for Donald J Trump, our president! ... America's future is in our hands! ... America, this is your moment. Will you stand for President Trump?"

The speech was oddly reminiscent of her aforementioned exaltation of Trump at the Republican National Convention in 2020. As with her earlier RNC appearance, Guilfoyle was lambasted over her fawning reverence for Trump. "Kimberly Guilfoyle is surrounded by people who really don't care about her embarrassing herself," theorized one X user. She was also criticized for painting a misleading picture of Trump's achievements as president. For instance, she claimed that Trump handed Biden a booming economy; as CNN pointed out in its fact-checking analysis, this is not entirely true, as the pandemic heavily impacted the economy during the latter part of Trump's presidency.