Kimberly Guilfoyle has always been “strategic” in how she “charts” her personal life and career in politics, which means that she will “swallow her pride,” “put a big smile on” and bide her time following a report alleging that her fiancée, Donald Trump Jr., has been cheating on her with a Palm Beach socialite.
This assessment of Guilfoyle’s Trump Jr. dilemma comes from Puck political reporter Tara Palmeri, during a conversation last week with Meghan McCain for her “Somebody’s Gotta Win” podcast. Palmeri believes that Guilfoyle is waiting to see if Donald Trump wins or loses the Nov. 5 election to decide whether she’ll stay in a relationship with his oldest son.
“If Trump wins, she stays with Don Jr.” Palmeri told McCain. “If Trump loses, watch Kimberly chart her own path.”
McCain pondered the future of Guilfoyle’s relationship with Trump Jr., following what she and Palmeri agreed was a pretty “damning” report in the Daily Mail about his alleged “dalliance” with a pretty, blonde model and influencer named Bettina Anderson.
The Daily Mail last week published photos of Trump Jr., 46, enjoying “an intimate brunch” on Aug. 17 with Anderson, 37, during which eyewitnesses said the two were seen “kissing” and “canoodling” in a booth at a swanky Palm Beach restaurant. The Daily Mail said their romance has become an “open secret” in elite Republican circles in and around the ritzy Florida community.
McCain, an anti-Trump Republican blogger and podcaster, brought up Trump Jr.’s alleged affair in the context of its potential impact on the Trump campaign. Aside from the “salaciousness of it,” McCain noted that Guilfoyle is a major “surrogate” for the GOP presidential candidate and has delivered fiery speeches on behalf of his MAGA politics, including at the 2020 Republican National Convention. She’s a “big fundraiser” for his campaign, McCain said.
The daughter of the late U.S. Sen. John McCain also said that she once worked with Guilfoyle at Fox News. “I would never underestimate her political abilities,” McCain said.
Palmeri agreed that Guilfoyle is “very smart” and “strategic ultimately,” which is why she probably hasn’t said anything publicly in response to the Daily Mail report or to the Palm Beach rumor mill.
One key thing about Guilfoyle’s life and career right now is that she’s become “closely identified with the Trump brand” since she began dating Trump Jr. in 2018, Palmeri said. The start of Guilfoyle’s romance with Trump Jr. coincided with her departure from Fox News — amid allegations of sexual harassment made by a former assistant, as the New Yorker reported.
Since then, Guilfoyle has been able to launch a career as MAGA’s “Eva Peron” — as Trump once referred to her — by getting engaged to his son, campaigning for him and becoming a trusted member of his inner circle.
“She’s gotten speaking engagements out of it,” Palmeri said about Guilfoyle. “She’s elevated her profile, some would say even beyond Fox News since she’s become part of the Trump family. I don’t see her abandoning that any time soon.”
Guilfoyle also has created a home with Trump Jr. in a gated, waterfront community in Jupiter, Florida, north of Palm Beach. The two purchased a mansion there in 2021, shortly after Trump lost the 2020 election and ignominiously left the White House, following the Jan. 6, 2021 insurrection at the U.S. Capitol.
“I think she ignores (the alleged affair), or works on it with Donald Trump Jr.,” Palmeri said. “Basically her career is closely tied to Donald Trump Jr. I don’t think she’d let (an) emotional reaction get in the way of her next move.”
“For now, I think Kimberly Guilfoyle will swallow her pride, put a big smile on,” Palmeri said.
“If Trump loses … and this is all over, I can see her pivoting,” Palmeri continued. She noted that Guilfoyle has done some major pivoting in her life. She first worked as a prosecutor in San Francisco and became a rising star in District Attorney’s office of the liberal California city.
During her career as a prosecutor, Guilfoyle infamously clashed with Kamala Harris, another rising political star, and has claimed that Trump’s Democratic opponent tried to block her from being hired by then-San Francisco District Attorney Terence Hallinan.
Guilfoyle was seen as politically moderate while she was married to Democrat Gavin Newsom and campaigned for him to be elected San Francisco mayor in 2003 — at the same that Harris successfully ran against Hallinan to become district attorney.
According to a report in the New York Times, Guilfoyle once “mused” about becoming San Francisco’s district attorney herself, with local political observers wondering if there could have been a Harris vs. Guilfoyle race for the office.
But Guilfoyle also wanted to become a media personality, so she moved to New York City. Following her divorce from Newsom in 2006, she became a conservative firebrand on Fox News.
Now, Guilfoyle may be contending with a new reality that could affect her future with the Trump family brand. The “damning” Daily Mail report described the ways that Trump Jr.’s romance with Anderson has become an “open secret” in Palm Beach. An eyewitness to their brunch date at The Honor Bar told the Daily Mail: “I guess they’re not trying to hide it. They’ve been seen together all over Palm Beach.”
Another source told the Daily Mail: “Kimberly either didn’t know about Bettina — or didn’t want to know. Did she hear whispers that Don Jr. was fooling around with someone else? Probably.”
The insider agreed with Palmeri and McCain that Guilfoyle is “no fool.” On the other hand, the insider also said to the Daily Mail: “It’s easy to deceive yourself when you’re so committed to someone and believe he’s committed to you.”
But Trump Jr. also has a history of alleged infidelity. At the time of his 2018 divorce from his wife Vanessa, the mother of his five children, Trump Jr. was the subject of lurid reports, alleging that he cheated on her in 2011 and 2012 with singer Aubrey O’Day. At the time, the Danity Kane singer had appeared as a contestant on his father’s reality TV show, “The Apprentice.”
Some might say that Anderson bears some resemblance to Vanessa Trump, with both women boasting slender model looks and long, light-colored hair. On her podcast, Palmeri also had some amusing observations about Anderson’s modeling career, saying she could be one of the “Worth Avenue models.” These are women in Palm Beach who parade around around the town’s upscale Worth Avenue shopping district, wearing clothes from local boutiques. They also stop in local restaurants, so that they can be seen wearing these clothes.
Palmeri said she learned about the “Worth Avenue models” when she began covering Trump’s White House for Politico. Palmeri said Anderson fits the type and it makes sense she’d come to Trump Jr.’s attention: “She’s attractive, young, she’s a Palm Beach socialite and they live there.”
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