Kimberly Guilfoyle Nearly Had A Very Different Role In Trump's Life Before Her Don Jr. Romance

Before she became Donald Trump's future daughter-in-law, Kimberly Guilfoyle was about to have a much different role in the former president's inner circle as the White House press secretary. Guilfoyle has been engaged to Trump's eldest son, Donald Trump Jr., since 2020, but four years earlier, she was a promising option for the forward-facing administration role.

According to anonymous sources who spoke to Politico in 2016, Guilfoyle was considered a better option than others because of her Latina heritage. "Do you want a white male representing the White House when half the country thinks the President is a misogynist?" The source said. "Who do you want talking about immigration? A Latino. When you have to make decisions about pro-life justices, do you want a man or a woman?"

Guilfoyle spoke highly of the potential position at the time, but she was unable to pursue the role further due to her extended contract with Fox News, where she worked as a legal analyst on "The Five." Ultimately, the role went to Sean Spicer, who was appointed to the position in 2017. However, this wouldn't be the first time Guilfoyle worked for her future father-in-law.

Although she didn't end up getting the position of White House press secretary, Kimberly Guilfoyle has been an active member of Donald Trump's ongoing political pursuits. She campaigned for Trump's re-election in 2019 with Donald's son and her then-boyfriend, Donald Trump Jr. One year later, Guilfoyle was appointed as the head of the Trump Victory Finance Committee, helping to raise public funds for the billionaire's re-election effort.

"The stakes have never been higher in a presidential election, which is why it's my honor to serve as National Chair for the Trump Victory Finance Committee," Guilfoyle said in a statement published by The Hill in January 2020. "The President's record of success is drawing unprecedented support from across the country, and these crucial financial resources will ensure he's in a strong position to win in November."

In addition to making money from public engagements and speeches, Guilfoyle received roughly $180,000 a year in exchange for her work with the Trump Victory Finance Committee. Lara Trump, wife of Eric Trump, also benefited from these controversial campaign paydays that were distributed through a separate marketing firm, Parscale Strategy, which some critics have accused the Trump campaign of doing to bypass Federal Election Commission guidelines that state all politically affiliated payments are disclosed to the public.

While Kimberly Guilfoyle said she would be excited to fulfill the role of former president Donald Trump's White House press secretary, perhaps it was better for Guilfoyle and Trump's relationship that she didn't. Even if a romance hadn't sparked between Guilfoyle and Trump's eldest son, Donald Trump Jr., Guilfoyle was an avid supporter and admirer of the then-POTUS. And as history has shown time and time again, Donald Trump doesn't always maintain the best relationships with his former press secretaries.

One such ex-press secretary, Stephanie Grisham, issued a dire warning to those who continue to work with the former president after he denounced another former press secretary, Kayleigh McEnany, on his social media platform Truth Social. "He uses you until there is no use for you anymore or until you dare to say something that could possibly be construed against him," Grisham said in a CNN interview in June 2023. 

So, considering Donald Trump's tempestuous relationship with more than one of his former press secretaries, maybe Guilfoyle's long-term Fox contract was a blessing in disguise. After all, tensions between the father-of-the-groom and the bride during Guilfoyle and Trump Jr.'s wedding would likely put a damper on the festivities.