Kimberly Guilfoyle will dump Don Jr over affair if Trump loses 2024 as she plans to 'chart her own path'

Kimberly Guilfoyle and Donald Trump Jr's relationship has come under scrutiny since reports surfaced about his alleged affair with a Florida socialite
UPDATED OCT 2, 2024
Kimberly Guilfoyle has been in a relationship with Donald Trump's eldest son, Donald Trump Jr, since 2018 (Getty Images)
Kimberly Guilfoyle has been in a relationship with Donald Trump's eldest son, Donald Trump Jr, since 2018 (Getty Images)

LOS ANGELES, CALIFORNIA: Kimberly Guilfoyle could end up dumping fiance, Donald Trump Jr, over his alleged affair if his father, Donald Trump, loses in the November election, claims political expert Tara Palmeri.

During a conversation with Meghan McCain for her 'Somebody’s Gotta Win' podcast, the Puck reporter said, "If Trump wins, she stays with Don Jr. If Trump loses, watch Kimberly chart her own path," as per GazetteXtra.

Meghan McCain says Kimberly Guilfoyle's political abilities shouldn't be 'underestimated'

Meghan McCain talked about the future of Kimberly Guilfoyle and Donald Trump Jr's relationship after agreeing with Tara Palmeri that the Daily Mail report about his alleged "dalliance" with Palm Beach socialite Bettina Anderson was pretty "damning." 

NEW YORK, NY - FEBRUARY 13: Donald Trump Jr. and Kimberly Guilfoyle pose backstage Gallery II in Spr
Donald Trump Jr and Kimberly Guilfoyle started dating in 2018 after her exit from Fox News (Getty Images)

The outlet published photos of Don Jr enjoying an intimate brunch with Anderson on August 17. Eyewitnesses claim the two were seen "kissing" and "canoodling" in a booth at the swanky Palm Beach restaurant.

In the September report, DailyMail mentioned that their romance is an "open secret" in elite Republican circles in and around the Florida community.

Keeping aside the "salaciousness" of the apparent affair, McCain noted that Guilfoyle is a major "surrogate" for Trump and has given fiery speeches on behalf of his MAGA beliefs, including the one at the 2020 Republican National Convention.

"I would never underestimate her political abilities," remarked the 39-year-old who used to work with Guilfoyle at Fox News. She also called Guilfoyle a "big fundraiser" for the Trump campaign. 

Tara Palmeri thinks Kimberly Guilfoyle doesn't want to risk losing the career she has built

Tara Palmeri added that Kimberly Guilfoyle is "very smart" and "strategic ultimately," which might be the reason why she hasn’t said anything publicly in response to the Daily Mail report or the Palm Beach rumor mill.

Palmeri further pointed out how the 55-year-old became "closely identified with the Trump brand" since she started dating Don Jr in 2018. The former president once dubbed her MAGA’s "Eva Peron" as she got engaged to his son, campaigned for him, and became a trusted member of his inner circle.

The Puck reporter said, "She’s gotten speaking engagements out of it. 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."

(Getty Images)
Kimberly Guilfoyle became a conservative firebrand on Fox News after her divorce from Gavin Newsom in 2006 (Getty Images)

She continued, "I think she ignores [the alleged affair], or works on it with Donald Trump Jr. 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."

"If Trump loses … and this is all over, I can see her pivoting," expressed Palmeri. 

MORE STORIES

Gregory Bovino warned that Illinois leaders’ criticism of immigration enforcement fueled hostility and put Border Patrol and ICE agents at greater risk
13 hours ago
The stipend is part of measures taken by the Trump administration to reduce illegal immigrants in US
1 day ago
The directive followed Donald Trump’s August 2025 executive order instructing law enforcement and military to immediately arrest flag burners
1 day ago
Sen Roger Marshall introduced the Passport Sanity Act to end gender-neutral passports citing security and Trump-era precedent
3 days ago
JB Pritzker went after Trump after he suggested alleged crime-ridden cities like Chicago could serve as a training ground for National Guard troops
4 days ago
With the US nearing a government shutdown, Donald Trump posted an AI-generated video mocking Chuck Schumer and Hakeem Jeffries as desperate
5 days ago
Trump revived his long-running clash with Jerome Powell by sharing a viral cartoon while demanding deeper rate cuts despite Fed independence
7 days ago
Supreme Court backs Trump’s move to freeze $4 billion in foreign aid, marking a major win for executive power
Sep 27, 2025
Pam Bondi also said the Justice Department was transferring inmates taken off death row under former President Joe Biden into maximum-security prisons
Sep 26, 2025
During a Wisconsin Senate immigration debate, the top Democrat lunged at chairman’s gavel, calling Republicans 'cowards' and questioning their faith
Sep 26, 2025