Little Ms. MAGA?
DNC arm candy?
Or a thing for any politician?
From Gavin Newsom to Donald Trump Jr., here's the dirty on Kimberly Guilfoyle's love life.
"The best is yet to come!"
When Kimberly Guilfoyle made her debut as Donald Trump Jr.'s paramour, most people likely
recognized her from "The Five" on Fox News.
But Californians might have remembered her as San Francisco's former First Lady.
As the Washington Post described it, she was, quote, "one half of a liberal power couple."
Current California governor, Gavin Newsom, was once mayor of San Francisco.
And Guilfoyle was his wife.
The Democrat duo was so politically hot and attractive, that Harper's Bazaar even called
them "The New Kennedys."
"It's gonna happen.
Whether you like it or not."
But in 2018, Guilfoyle admitted to the Washington Post that she's actually been a registered
Republican since she was 18.
And as a senior Trump advisor alleged to Insider of Guilfoyle and Donald Trump Jr.,
"[They're] like the prom king and queen of MAGA land."
It's not just Melania Trump who spent her early days working it for the cameras.
According to Insider, Guilfoyle once modeled for Macy's and Victoria's Secret catalogs.
As she explained to Cosmo,
"I knew I wanted to go to law school, and I wanted to have the funds to do so.
[…] I learned how to cue into my own autonomy as a woman.
I don't have any regrets about all of the jobs in the different fields that I've worked
in."
"I won't do anything that the next morning, they told me, 'You will regret.'"
She also hustled for D.A.s in both Los Angeles and San Francisco.
And as a former colleague recalled to the Washington Post,
"She was a down-to-earth, classy prosecutor."
In 2001, Guilfoyle married Gavin Newsom, having met years earlier while she was working in
the D.A.'s office, and his government career was on the rise.
The San Francisco Chronicle called their wedding "the social event of the year."
Gilfoyle's father, Anthony Guilfoyle, even served as a political advisor to Newsom while
the couple were married.
He stayed on after they divorced.
Newsom then became mayor of San Francisco in 2004.
And Guilfoyle was by his side as First Lady, even once hosting Prince Charles and Camilla.
As Guilfoyle told People,
"I spent three days with them, and it was a wonderful experience.
During one of the formal dinners, I was sat next to Prince Charles who was kind enough
to share the rest of his apple tart dessert with me."
"I said, 'Are you gonna finish that?
I'll take a bite.'"
But her life in the Mayor's Mansion would be short-lived.
Guilfoyle and Newsom divorced a little more than a year into his first term.
Newsom and Guilfoyle's bicoastal marriage dissolved shortly after he took the mayor's
office.
According to the Washington Post, insiders close to the couple alleged that they were
just using each other to advance their careers.
At the time, Guilfoyle landed a TV job based in New York City just after Newsom was sworn
in.
At the very least, that scenario put a distance between them.
Then there was Newsom's affair with his campaign manager's wife, Ruby Rippey-Tourk.
During a 2007 press conference, Newsom later confirmed:
"Everything you've heard and read is true.
And I am deeply sorry about that."
Guilfoyle has kept mum on the affair, but she didn't mince words years later at the
RNC in 2020:
"If you want to see the Socialist Biden/Harris future for our country, just take a look at
California."
Commending some of the state's innovative policies and stunning landscape, as well as
the bounty of money being pumped into its economy, she warned:
"The Democrats turned it into a land of discarded heroin needles in parks, riots in streets
and blackouts in homes."
Guilfoyle moved on from her 2005 divorce relatively quickly, remarrying in May 2006, according
to The New York Times.
Her second husband was Eric Villency; the CEO of a family-founded furniture chain.
And like Guilfoyle, he also happened to be a former model.
To many people, though, he's best known as the guy who invented the SoulCycle bike.
"You are destined for greatness."
The couple welcomed their son Ronan in 2006.
But their marriage ended almost three years later.
Still, despite any hard feelings, it appears the former duo is on good terms.
Guilfoyle even comments heart emojis on her ex's Instagram posts with their son.
Guilfoyle reportedly met Donald Trump Jr. through mutual friends at a party, according
to the Washington Post.
Don Jr. had been married to his first wife, Vanessa, until 2018.
But the current couple and their exes appear to be fairly chummy.
There are even old photos of Trump and Vanessa and Guilfoyle and Eric posing together at
a party.
Once Don Jr.'s divorce was announced, Page Six broke the news that he and Guilfoyle were
dating.
A source dished to the outlet,
​​"Don Jr. and Kimberly are seeing each other and are having a great time.
While he wants to respect the privacy of his family, he is getting divorced, and he enjoys
Kimberly's company."
"Listen, we're havin' a great time."
At the time, Guilfoyle was busy co-hosting "The Five" on Fox News.
When Guilfoyle and Don Jr. began their relationship, Trump senior was already in the Oval Office.
And rather than keep their respective government connections separate from their romance, the
couple embraced a public life in politics.
Apparently, part of what drew Don Jr. to Guilfoyle was her on-air support of his dad's presidential
campaign.
As he told the Washington Post,
"When everyone else said that Hillary was unstoppable, Kimberly stood firmly with my
father."
"The people across the country, they really relate to him."
Just a month after they went public with their relationship, the couple attended the Montana
Republican Convention together, with Don Jr. even mentioning Guilfoyle by name in a speech.
They appeared at many more political events together, sometimes locking lips onstage.
And it all culminated in Guilfoyle's notoriously fiery speech at the RNC in 2020.
"I'm big on real estate.
I really, really love — people call me 'Mini Trump.'"
When Guilfoyle and Don Jr. aren't hitting the campaign trail, they're snapping up some
pretty impressive real estate.
According to Insider, in 2019, they bought a 7-bedroom home in the Hamptons together
after just a year of dating.
They sold the house for $8.14 million a year later, at nearly double what they originally
paid.
Soon after that, People reported that they picked up a $9.7 million mansion in Jupiter,
Florida, close to the family's much talked about resort, Mar-a-Lago.
Since most of the Trump clan have jumped ship to Florida, it seems Don Jr. and Guilfoyle
should have plenty of company in their enormous new house.
Since Guilfoyle and Newsom broke up in 2005, Newsom had enjoyed quite the career trajectory.
After serving five more years as Mayor of San Francisco, he later became the Governor
of California.
When public radio's KQED asked Newsom, who is a Democrat, about his strange connection
to the Trumps, he told the outlet in 2018,
"I think in those terms, I'm still trying to come to grips with all of it.
[…] No, it's fine.
I wish her well and them well.
And we see the world, clearly, with a different set of eyes politically."
Back in 2004, when she appeared with Newsom on "Charlie Rose," Guilfoyle had kind words
for her then-husband's budding political career, saying,
"I knew that he had the vision and the discipline, and as it's turned out, the courage to be
in politics to do the right thing."
But, years later, Newsom and Donald Trump Sr. traded several scathing barbs.
"Governor Newsom, honestly, is living in a different world."
Although the California governor appeared to wish his ex well with her political alliances,
as we know, Guilfoyle called out Newsom's governance of California as an example of
socialist policies gone bad, during her speech at the 2020 RNC.
With a combined six children and three ex-spouses, it's safe to say that both Don Jr. and Guilfoyle
might be toting a little baggage.
But while Guilfoyle has a seemingly amicable relationship with her son's father, it seems
Don Jr. and his ex-wife Vanessa are just as friendly.
Despite the timeline, Guilfoyle and Vanessa's relationships with Don Jr. did not overlap.
Vanessa filed for divorce in March 2018.
And according to People, Don Jr. and Guilfoyle were first seen together a month later.
By all accounts, there seems to be no bad blood between any of them.
Vanessa even stuck up for Guilfoyle on Twitter in June 2018, after pundits called for her
firing from Fox News — just because she was dating Don Jr.
Vanessa tweeted,
"The lengths people will go to attack a woman simply because she's dating Don.
We've been separated for over 9 months and respect each other's decisions & privacy."
People noted that Vanessa even "liked" a few of Don Jr.'s tweets even after their separation.
And, that's despite the fact that her family is believed to be more liberal than the Trumps
are.
According to the Daily Mail, Don Jr. and Guilfoyle low-key revealed their engagement at the start
of 2022.
And if it was true, the timing was perfect for it.
Don Jr's divorce was finalized, and the couple had seemingly taken a break from campaigning.
Not many details are known about the proposal or any possible wedding plans, but a source
told the outlet,
"Kim has been wearing her engagement ring, and both are very excited about blending their
families."
"I can't get enough of that Jr., I gotta tell ya'."
Eagle-eyed Instagram followers spotted a diamond sparkler on Guilfoyle's left ring finger in
a Christmas post from January 1, 2022.
And People suggested that the shot was likely snapped at Mar-a-Lago.
It seems pretty clear that wherever the political tides take them, this couple's work and romantic
lives will remain intertwined for as long as they're together.
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