Inside Donald Trump's complicated relationship with Kimberly Guilfoyle: From mocking her to celebrating birthdays

Tracing the dicey relationship between former POTUS Donald Trump and Kimberly Guilfoyle

Ever since former Fox News host Kimberly Guilfoyle started dating Donald Trump Jr in 2018, she has been a prominent figure in conservative media. A Trump advisor humorously referred to the couple as the "prom king and queen of MAGA land" in an interview with Business Insider. Known for her outspoken personality, Guilfoyle is famous for her unapologetic support of the MAGA movement. Unsurprisingly, former president Donald Trump appointed Guilfoyle to a prominent fundraising role during his unsuccessful reelection campaign in 2020. Notwithstanding the outcome of the 2020 presidential election, both Guilfoyle and Don Jr have returned to the political spotlight. This time, Kimberly Guilfoyle has once again thrown her support behind her future father-in-law after an attempted assassination on the ex-POTUS on Saturday, July 13. Speaking with Sky News, she praised the 78-year-old MAGA figurehead’s resilience, stating, "He's very resilient, 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." The ongoing presidential race between Donald Trump and presumptive Democratic nominee Kamala Harris may put the spotlight on Guilfoyle's influence on her prospective father-in-law. Despite many similarities, the relationship between Trump and Guilfoyle has faced its fair share of challenges.

Donald Trump was dismissive of Kimberly Guilfoyle

Although former president Donald Trump maintains a positive relationship with Jared Kushner, who is married to his daughter Ivanka Trump, his feelings toward Kimberly Guilfoyle are more complicated. Before getting together with Guilfoyle, Donald Trump Jr was married to Vanessa Trump, who initiated divorce proceedings in 2018. It appears that the senior Trump often finds it difficult to get along with the partners of his eldest son. In 2019, The Atlantic reported that the 45th POTUS never liked Vanessa, possibly due to her alleged previous romantic involvement with a member of a street gang, or because she allegedly insulted her father-in-law using an ableist slur at a fashion show. However, when his son began a new relationship with Guilfoyle, Trump Sr reportedly held even stronger negative feelings toward her. This reportedly stemmed from the Fox News host's attempt to become his press secretary, with the then-president belittling Guilfoyle as supposedly lacking intelligence and 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 aforementioned outlet. Furthermore, there have been allegations that both Don Jr and his father sought the affection of Guilfoyle. An advisor informed the aforementioned publication that at one point, the latter supposedly made inappropriate comments about Guilfoyle and tried to find out if she was single, despite being married to Melania Trump.

Sources claim it wasn't just Donald Trump who had an issue with Kimberly Guilfoyle

In 2022, a source close to Eric Trump told Page Six, "The vibe is that the [Trump] family doesn't like Kim. She is trying too hard to be in the family." When questioned about this, Eric countered, "I completely disagree with the narrative and happen to think the world of Kimberly." Despite this, speculation grew that there was tension between Donald Trump and Kimberly Guilfoyle when he briefly appeared at her and Don Jr's Toys for Tots fundraiser hosted at their luxurious home. Reportedly, former president Trump only stayed for half an hour at the event, which notably did not include Ivanka Trump and Jared Kushner. While a source claimed that Ivanka and Kushner's absence was due to a scheduling conflict, rumors of discord between the couple and Guilfoyle were already in circulation. According to sources cited by the New York Magazine's Intelligencer, Guilfoyle's presence at the couple's Fourth of July party apparently overshadowed Ivanka and Kushner, leading to Don Jr being asked to seek approval before bringing a guest to future events. Subsequently, rumors surfaced that Trump Sr prohibited Guilfoyle from attending the family's Thanksgiving dinner at Mar-a-Lago, although both the White House press and Don Jr denied this claim.

Donald Trump and Kimberly Guilfoyle are thought to have similar temperaments

Donald Trump has unquestionably made a lot of powerful enemies over the years. His confrontational personality has consistently angered former aides and friends, some of whom decided to write books about their interactions with him. Trump and Kimberly Guilfoyle both share a fiery temperament. After leaving Fox News in 2018, Guilfoyle became a vocal, assertive, and outspoken figure in the MAGA circuit, delivering passionate speeches and appealing to the populist vote. "It's interesting to me that Donald Trump Jr ended up with a female version of his father," remarked one of Guilfoyle's former colleagues to Business Insider. Before being in a relationship with Guilfoyle, Don Jr had always been in his father's shadow. The former president was even reluctant to name his eldest son after him, supposedly fearing that he might turn out to be a "loser." However, with Guilfoyle's apparent guidance, Don Jr has carved out a significant populist figure of his own. Even though former president Trump initially seemed hesitant to have her as his press secretary, he eventually appointed Guilfoyle as an advisor in his 2020 presidential campaign. It appeared as if he was finally starting to warm up to Guilfoyle, a woman who shares so many characteristics with him.

Donald Trump allegedly taunted Kimberly Guilfoyle over her ex-husband

Kimberly Guilfoyle ended her first marriage to then-San Francisco mayor Gavin Newsom in divorce. In 2006, a year after her split from Newsom, she married furniture heir Eric Scot Villency. However, this marriage also ended in divorce three years later. Guilfoyle's relationship with California Governor Gavin Newsom has sparked controversy. Newsom, a Democrat, has clashed with Republicans, including the right of the Democratic party, on issues such as abortion, gun safety, and healthcare. This is contrary to his ex-wife's views, who has been labeled by some as an alt-right grifter. It is to be noted that she supported the contentious overturning of Roe v Wade in 2022, while Gov Newsom has supported legislation to make it easier for pregnant women to obtain abortions following the Supreme Court's draconian ruling. Donald Trump reportedly found it amusing that his future daughter-in-law was once in a relationship with Newsom and used it to mock her. According to the book ‘The Hill to Die On’ by Anna Palmer and Jake Sherman, Trump even made fun of Guilfoyle during a fundraiser in 2018. The ex-president went on an invective-filled rant about Newsom and his liberal policies, asking Guilfoyle, "Kimberly, you know him, right?" (via People). The awkward gag was met with some uncomfortable laughter from the guests, as noted by Palmer and Sherman.

Donald Trump gave Kimberly Guilfoyle a large sum of money

In 2020, during Donald Trump's reelection campaign, it was uncovered that he was allegedly using campaign funds to pay Kimberly Guilfoyle substantial amounts of money. According to two unnamed GOP sources who spoke to the HuffPost, Guilfoyle, and Lara Trump, Eric Trump's wife, were each receiving $15,000 monthly through campaign manager Bradley Parscale. At the time, Parscale stated, "I can pay them however I want to pay them." This raised concerns from some who argued that Guilfoyle did not deserve such a large payment, reaffirming previous claims that former president Trump regards her as merely a Fox News figurehead. "She's doing stuff, but she's just like this silly cheerleader," a White House advisor remarked, adding. "She gets on these donor calls, and it's ridiculous." There were also ethical questions raised regarding redirecting huge sums of donor money to Donald Trump's associates. "A lot of people close to Donald Trump are getting rich off of his campaign," stated Paul Ryan, who was the vice president for policy and litigation at the government accountability group Common Cause at that time. "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 receiving tens of thousands of dollars for giving concise speeches at Trump rallies, which led to further controversy over the appropriation of donor funds, as reported by USA Today.

Donald Trump found Kimberly Guilfoyle 'annoying'

Kimberly Guilfoyle started working with former Missouri governor Eric Greitens' Senate campaign in 2021. "[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." Former president Donald Trump reportedly grew furious over this, loathing Greitens because of reports that the governor had sexually assaulted a woman he was seeing outside of his marriage. Aides claimed that Trump, who has himself faced numerous accusations of sexual misconduct, was unable to understand why his potential daughter-in-law would be connected with someone as polarizing and reprehensible as Greitens. "Trump thinks Greitens is problematic, and that Kim is annoying," a Trump advisor informed Politico. "He said, 'Why the f*** is she working for him?'" As a result, Trump was reportedly concerned that Guilfoyle's association with Greitens would appear to suggest that he had endorsed the volatile lawmaker. These concerns were undoubtedly made worse by Greitens' previous statement in which he compared the Trump campaign to his senatorial bid. Guilfoyle, for her part, denied the story.

Kimberly Guilfoyle is never one to stop praising Donald Trump

The relationship between Donald Trump and Kimberly Guilfoyle may be complicated, but she certainly expresses admiration for her future father-in-law. In 2020, she gained attention for a notably spirited speech at the Republican National Convention, where she fervently endorsed Donald Trump for President in what could be considered an unhinged show of support. Guilfoyle stated, "President Trump is the leader who will rebuild the promise of America," (via People). She emphasized, "We build things up, we don't burn them down. We kneel in prayer and we stand for our flag." Was her reference to kneeling in prayer and standing for the flag a subtle signal to NFL players who knelt during the national anthem to protest police brutality against Black people? This is plausible, considering Guilfoyle's previous criticism of Colin Kaepernick. Trump also openly criticized NFL players who knelt during the national anthem, condemning them as unpatriotic and suggesting that they should leave the country. This appears to be another viewpoint shared by both Trump Sr and Guilfoyle. On the ‘Late Show’ with Stephen Colbert, Guilfoyle was satirized for her speech, with Colbert labeling her as the "Trump Jr girlfriend and vengeful banshee who will haunt your dreams." As time passed, the similarities between Guilfoyle and Trump became increasingly noticeable. On an episode of her show in 2023, Guilfoyle began to sound remarkably similar to Trump as she praised his supposed positive qualities. "He has unbeatable stamina," she claimed (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?"

Kimberly Guilfoyle was disappointed she couldn't speak at Donald Trump's 'Save America' rally

During the violent Capitol riots, there was a significant pushback against the Trump brand. On January 6, 2021, a group of Trump supporters stormed the Capitol building, believing the election had been "stolen" to protest Joe Biden's presidential victory, resulting in the deaths of five people. Former president Trump has long been accused of encouraging the violence that occurred during the January 6 riots. On the day of the riots, he organized a ‘Save America’ rally, during which he called on his supporters to take action. According to the Associated Press, he said, "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." In November 2021, it was alleged by ProPublica that Kimberly Guilfoyle had boasted about raising $3 million for the ‘Save America’ rally and tried to coordinate far-right speakers to appear alongside Trump. She also had hoped to speak at the rally herself, but that did not go as planned. When former Trump aide Katrina Pierson told Guilfoyle in a text message that the ex-president had personally arranged all the speakers, Guilfoyle expressed her desire to introduce her fiance, Donald Trump Jr. "[I] raised so much money for this," she wrote. "Literally one of my donors Julie at 3 million." Guilfoyle denied the allegations regarding raising funds for the rally.

Donald Trump joined Kimberly Guilfoyle in celebrating her 54th birthday

In 2023, Donald Trump made a surprising appearance at Kimberly Guilfoyle's 54th birthday in Jupiter, Florida. It was unexpected since Trump rarely leaves his Mar-a-Lago estate in Palm Beach. "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 pm and left before 10 pm," 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." The former president was seen dancing energetically and gave a speech praising Guilfoyle, saying, "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." However, earlier reports hinted at tensions between Guilfoyle and other members of the Trump family. Notably, Ivanka Trump and Jared Kushner, who were invited, but did not attend the birthday celebrations, citing a prior commitment.

Kimberly Guilfoyle was derided for her impassioned speech for Donald Trump

Kimberly Guilfoyle expressed her steadfast support for Donald Trump by delivering a rallying speech at the Republican National Convention shortly after the assassination attempt on the former president. Guilfoyle's speech was described as "unhinged," involving a lot of passionate yelling as she seemingly imitated Trump while praising her future father-in-law in Milwaukee. "I know personally what every American has now seen with their own eyes!" she shouted (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?" This speech bore a striking resemblance to her previous praise of Trump at the Republican National Convention in 2020. As with her earlier appearance at the RNC, Guilfoyle faced criticism for being excessively approving of Trump. She was also chastised for presenting a misleading portrayal of Trump's accomplishments as president. For instance, she asserted that Trump left Joe Biden with a thriving economy; however, CNN's fact-checking analysis pointed out that this is not entirely accurate, as the economy was severely impacted by the Covid pandemic during the latter part of Trump's presidency.