5 Times Kimberly Guilfoyle Shamelessly Sucked Up To Donald Trump

Despite getting her professional start as an attorney, Kimberly Guilfoyle gained mainstream recognition as a media personality, working as an analyst and contributor for various TV channels, including Court TV, CNN, and Fox News. Additionally, Guilfoyle became well-known to the public as the former First Lady of San Francisco during her marriage to Gavin Newsom, who served as the city's mayor from 2004 to 2011. They divorced in 2006.

Nowadays, Guilfoyle is widely recognized as the fiancee of Donald Trump Jr., whom she started dating in 2018. Notably, she had ties with the Trump family before getting together with Trump Jr., as she had been considered for the position of press secretary in Donald Trump's administration. Even though she ultimately didn't land the high-profile role, Guilfoyle wiggled her way into the Trump family through romance. As politics is a family affair for the Trumps, it came as no surprise that Guilfoyle emerged as one of Trump's most outspoken supporters during both of his presidential campaigns. In 2018, The Washington Post described her as a "conservative cheerleader for President Trump."

Working under Trump in any capacity appears to require praising him, and Guilfoyle is no stranger to shamelessly sucking up to her future father-in-law. Despite this, a source cited by Politico claims that Trump isn't too fond of Guilfoyle, which doesn't stop her from praising him in the most fawning ways.

Kimberly Guilfoyle once compared Donald Trump to a mob boss, inadvertently pointing out how Trump has gotten into more trouble with the law. In August 2023, following Trump's fourth indictment, she appeared on Newsmax to comment on the unfairness of the accusations against her future father-in-law. While Guilfoyle undoubtedly had the best of intentions, the way she went about proving her point was painful to witness.

She started her rant off by accusing Fulton County District Attorney Fani Willis of using the indictment "for her own political purposes and advancements and fundraising off of this," OK! reported. Notably, Trump was charged under Georgia's Racketeer Influenced and Corrupt Organizations (RICO) law, which Guilfoyle thought would be important to note. "It's just absolutely ridiculous," she stated before bringing up John Gotti, a notorious American mobster who passed away in prison in 2002. "And John Gotti? OK, can you imagine RICO violations? John Gotti never even had four indictments at once. There's no mob boss, let alone they do this to President Trump," Guilfoyle said awkwardly.

Her confusing statement didn't fly under the radar online, with social media users reveling in Guilfoyle's unflattering comparison. "One [of] the best Trump spokespersons out there," one X (formerly Twitter) user jokingly shared, while another quipped, "When John Gotti is your criminal benchmark."

Another one of Kimberly Guilfoyle's shameless bids to curry favor with Donald Trump was televised and, again, fell flat. In December 2023, during another appearance on Newsmax, Guilfoyle was asked about Trump's potential authoritarian tendencies should he secure a second term in office. Notably, just days earlier, Trump told Fox News host Sean Hannity that he wouldn't act like a dictator if re-elected in 2024, "except for day one." He added, "I want to close the border, and I want to drill, drill, drill," per AP News.

Despite Trump's own declarations regarding the nature of his politics, Guilfoyle attempted to clear the air. "Trump is a man who respects the law and is going to follow it, Guilfoyle said on Newsmax's "Rob Schmitt Tonight." She continued, "[He] is going to make sure he has people who aren't political hacks in positions of power and restore the integrity of our governmental institutions," as shared on X. However, Guilfoyle's portrayal of Trump as a law-abiding citizen contrasts starkly with the 91 criminal counts the controversial businessman is facing.

Social media users made it their mission to point out the discrepancy, calling Guilfoyle out for glorifying Trump. One X user described the Trump family as a cult, adding, "Gaslighting in process." Another person spotlighted Trump's attempt to claim presidential immunity in the legal cases against him to evade the hand of justice, which Guilfoyle conveniently failed to mention.

In 2020, everyone talked about Kimberly Guilfoyle's speech at the Republican National Convention, which was widely criticized for its fervent delivery and Guilfoyle's false claim that both of her parents were immigrants, in an apparent attempt to connect with the audience. Fast forward three years, and Guilfoyle took a public stance against the RNC during an episode of Steve Bannon's "War Room" podcast on Real America's Voice (via X).

As she discussed Donald Trump's 2024 presidential run, Guilfoyle took aim at Republicans who didn't endorse her future father-in-law, branding them as "traitorous, disloyal, and unqualified." She went on to claim none of the individuals associated with Trump's Republican opponents' campaigns will be considered for positions in a potential Trump administration, stating, "None of those people — fake Republican RINOs, the RNC — all those people have to go. They're not gonna be part of our team. They suck."

In yet another transparent bid to suck up to Trump, Guilfoyle named some of the people she'd like to see working for him, including Kash Patel, Richard Grenell, and Bannon, all Trump supporters who've had their fair share of controversies. Patel, who is an attorney, threatened to sue American journalists and government officials critical of Trump, while Bannon was accused of spreading misinformation in favor of Trump, most notably ahead of the 2020 election. Grenell, a former diplomat, has faced allegations of corruption while working for Vladimir Plahotniuc, the disgraced Moldovan oligarch.

Kimberly Guilfoyle isn't even attempting to hide her need to get on Donald Trump's good side, as she once went as far as to praise his physical endurance. Likely meant to undermine President Joe Biden, who is often described as frail and unfit to lead by his opponents, Guilfoyle gushed about Trump's "unbeatable stamina" during an episode of her Rumble show, "The Kimberly Guilfoyle Show."

As she tried to highlight Trump's presidential vigor, Guilfoyle stated, "Look at Donald Trump — seriously. [He's] as alert as ever, ready to confront all of our nation's problems head-on," as shared on X. She added, "That is what we need in a leader. Not to mention his golf game when he hits holes-in-one; I've seen it personally." However, Trump's actual physical condition isn't that great. His unhealthy diet and lifestyle have been widely reported, with his doctors resorting to tactics like sneaking vegetables into his meals when he had to lose weight. "We were making the ice cream less accessible; we were putting cauliflower in the mashed potatoes," Trump's former doctor told The New York Times in 2020.

In response to Guilfoyle's efforts to portray Trump as robust, X users flocked to mock her statement. "I must be Superman then," joked one user, while another pointed out how Trump avoided getting drafted for the military in the 1960s due to a medical deferment. It seems Trump's stamina might be situational rather than consistent.

Donald Trump Jr., Donald Trump's eldest child, is well-known for his unwavering support of his father, particularly in the public realm. Given his outspoken presence on social media and in interviews, it's not surprising that his fiancée chose to align with the praise narrative to suck up to her future father-in-law. During their joint appearance on ABC's "The View" in 2019, as reported by People, Kimberly Guilfoyle and Trump Jr. lauded Trump across the board, making Guilfoyle look as toady as it gets.

Although Trump Jr. was primarily responsible for showering his father with praise during the interview, it's Guilfoyle's awkward comments that linger in our memories. While Trump Jr. discussed the Trump family's financial gains from a Washington, DC, hotel that opened shortly before Trump was elected in 2016, Guilfoyle jokingly interjected, "Thank God [Trump] is president; he knows how to make a buck!"

While the awkwardness would've been bearable had Guilfoyle stopped there, when asked about her wedding plans with Trump Jr., she said she would marry him "if he can get the president re-elected," referring to Trump. Despite having limited opportunities to contribute during the intense discussion, Guilfoyle made sure that the few remarks she made emphasized her devotion to Trump, and we're not talking about the junior one.