Being a MAGA insider can offer perks galore, but it can also be fraught with peril. Kimberly Guilfoyle knows this better than anyone. Once a fixture of Trump's ever-evolving group of insiders, her circumstances have changed radically—and rapidly.
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00:00Being a MAGA insider can offer perks galore, but it can also be fraught with peril.
00:05Kimberly Guilfoyle knows this better than anyone. Once a fixture of Trump's ever-evolving
00:10group of insiders, her circumstances have changed radically — and rabidly.
00:15Given her history, Kimberly Guilfoyle would seem an unlikely candidate to become
00:19a leading right-wing figure. After all, she was once married to California Governor Gavin Newsom,
00:25one of the shining stars in the Democratic Party. The union didn't last,
00:29and after their four-year marriage ended in divorce, she married businessman Eric Valencia
00:34in 2006. That marriage was also doomed to fail. However, during her brief three-year stint as
00:39Valencia's wife, she and her future ex crossed paths repeatedly with Donald Trump Jr. and his
00:45then-wife Vanessa Trump.
00:46These are the two most important women in my life."
00:48During her marriage to Valencia, Kimberly's politics shifted to the right, moving from
00:53her nonpartisan TV gig at Court TV to Fox News, the deeply conservative cable news channel.
00:59It was during her early years at Fox News that she first began encountering members
01:03of the Trump family at various society functions in New York City. She was first introduced to
01:08Donald Trump Jr. at a party, while both were married to other people. They were friendly,
01:12but would become even better acquainted about a decade later.
01:16After Donald Trump's victory in the 2016 presidential election,
01:20Kimberly put both her Fox News cred and her Trump family connections into action when,
01:25in 2017, she made a bid to become White House press secretary.
01:29At the time, Trump reportedly looked to shake up the White House communications strategy,
01:34having grown unhappy with then-press secretary Sean Spicer. According to a New York Times report
01:39about the then-president's plans, Trump floated Kimberly's name for the position.
01:43Kimberly confirmed that report when she told the Mercury News she was in serious discussions to
01:48take on a role within the Trump administration, potentially replacing Spicer as White House
01:53press secretary, saying,
01:55"...I'm a patriot, and it would be an honor to serve the country. I think it'd be a fascinating
01:59job. It's a challenging job, and you need someone really determined and focused,
02:04a great communicator in there with deep knowledge to be able to handle that position."
02:08Speaking on Fox News in what seemed to be an on-air job interview,
02:12Kimberly shared her philosophy of how a press secretary could succeed when working
02:16with the freewheeling Trump. If you want to be successful and do communications with President
02:20Trump, you have to be someone who he actually wants to spend a little bit of time with.
02:25"...He can't stand to see things not done the right way."
02:29She did not get the job, however, which ultimately went to Sarah Huckabee Sanders.
02:34It wasn't long after Kimberly's name was floated as a potential White House press secretary that
02:38she began popping up in gossip columns. It started in March 2018, when Vanessa Trump announced that
02:44she'd split from Don Jr. and had begun divorce proceedings. In May, Page Six reported that
02:49Donald Trump's eldest son had already moved on and was dating Kimberly, with a source telling
02:54the tabloid,
02:55"...Don Jr. and Kimberly are seeing each other and are having a great time. While he wants to
03:00respect the privacy of his family, he is getting divorced. And he enjoys Kimberly's company."
03:05While neither confirmed it, Kimberly and Don Jr. weren't exactly keeping their budding romance
03:10under wraps. In June, the two went Instagram official pictured with Poison frontman Brett
03:15Michaels, of all people. Years later, Kimberly recalled how the two went from acquaintances to
03:19lovers, telling Metropolitan Palm Beach Magazine in 2022,
03:23"...Don and I knew each other for years. But when we went on one date years later, that was it.
03:28Sparks. In fact, we have been together from that night on, happily ever after."
03:33By June 2018, Don Jr. and Kimberly were a full-fledged couple. If the Make America
03:39Great Again movement were a wedding cake, tiny plastic versions of them would sit on top.
03:43That was apparent when Don Jr. took her on Every Woman's Dream Date, as his plus one to the 2018
03:49Montana Republican Convention, where he delivered a speech before the two went on a fishing and
03:53hunting expedition that he joked was a compatibility test. Don Jr. told the crowd,
03:58"...We're going to take her fishing tomorrow, then shooting. This is a miniature test to see
04:02if she really likes it, or if she's going to pretend to like it, but either way, we're going
04:07to have a good time. Or at least I will." Not long after that, Page Six reported on their
04:11sickeningly sweet pet names for each other. An alleged friend told the outlet that Kimberly
04:16called Don Jr. mints, while his term of endearment for her at the time was Pooh Bear.
04:21As the official girlfriend of Donald Trump Jr., Kimberly entered the Trump family's inner sanctum.
04:26Kimberly, however, was far more than just arm candy. She put herself into service of the
04:30president and his MAGA movement, becoming a Trump surrogate and delivering fiery speeches
04:35at his rallies. Meanwhile, her influence on Don Jr. had increased his MAGA cachet,
04:40with sources claiming that she'd groomed and molded him in a manner that increased
04:44his popularity with his notoriously fickle father, and by extension, his political base.
04:49One publicist and former gossip columnist told Business Insider,
04:52"...She's definitely made Don Jr. more serious. She's had years and years on TV.
04:57She's helped guide and train and been very influential in Don's increasingly very secure,
05:02very formidable, very opinionated television personality."
05:05"'The American public gets it, Sean. They see through this nonsense."
05:09Meanwhile, another insider pointed out Kimberly's similarities to her beau's father,
05:13implying his attraction to her was due to his daddy issues, saying,
05:17"...It's interesting to me that Donald Trump Jr. ended up with a female version of his father."
05:22Kimberly's rise within the rank of Trump-land was evident during the 2020 Republican National
05:27Convention, when she was chosen to deliver a keynote speech. That speech was, well,
05:32it was something. Not only did she describe Donald Trump's opponent Joe Biden as a raving socialist,
05:37but she also made a few eyebrow-raising claims about the Democrats.
05:41"...They want to steal your liberty, your freedom. They want to control what you see and think."
05:47While her stride in speech appeared to go over well at the convention,
05:50that certainly wasn't the case elsewhere. One New York Times TV critic wrote that
05:54she was on a mission to make America deaf again, and late night hosts had a field day.
05:59"...Trump Jr. girlfriend and vengeful banshee who will haunt your dreams."
06:03"...The best is yet to come."
06:07"...I want to wish a speedy recovery to anyone who was listening on headphones."
06:11Kimberly and Don Jr. had been the preeminent MAGA power couple for years when they made a
06:152019 appearance on The View. They were asked about whether they'd be walking down the aisle
06:20anytime soon, and made it clear their priority was to get the president re-elected. That did
06:24not happen.
06:26"...Joseph R. Biden Jr. is elected the 46th president of the United States."
06:31With Donald Trump exiting the White House and returning to Mar-a-Lago,
06:34the rest of the Trump family followed suit and made Florida their home base.
06:38In 2021, the Palm Beach Post reported that Kimberly and Don Jr. had been scoping out
06:43a waterfront home in Admirals Cove, a gated community in Jupiter, Florida. The couple
06:48eventually pulled the trigger on the $9.7 million purchase of an 11,300-square-foot mansion,
06:55situated just 20 minutes from Mar-a-Lago.
06:58Status-wise, it's one thing to be the girlfriend of Donald Trump Jr.,
07:01but quite another to be his fiancée. In 2022, Kimberly took to Instagram to share
07:06a photo of herself and Don Jr. posing in front of a festive Christmas tree at the White House.
07:11His hand on her hip, the ring finger on her left hand sported a large engagement ring.
07:15Kimberly wrote in the caption,
07:17"'Don, you are strong, smart, courageous, funny, and the love of my life.
07:21I can't wait to spend the rest of our lives together.'"
07:23Their engagement, however, may not have been as recent as most people had assumed.
07:27As a source told Page Six, they'd actually been engaged for well over a year. The source said,
07:32"'They've kept it private for the past year as they settled into life in Florida after
07:36moving from New York. Both are focused on their children. They have six between them,
07:40and their work.'"
07:42After Donald Trump won the 2024 presidential election, the obvious assumption was that
07:46Donald Trump Jr. and his fiancée would tie the knot at some point in the not-too-distant future.
07:52Those assumptions, however, hit the skids when reports emerged that Don Jr. had been
07:56seen enthusiastically kissing a woman who was decidedly not his fiancée. According to the Daily
08:01Mail, eyewitnesses saw Don Jr. canoodling in a bar with Palm Beach socialite Bettina Anderson,
08:07with Kimberly nowhere in sight.
08:09Though sources told the outlet that the two kissed each other no less than three times.
08:13The source said,
08:14"'She seemed totally smitten with Don, and he with her. They were definitely on a date.
08:18They weren't exactly making out, but the kisses were romantic,
08:22and you could tell they were intimate with each other.'"
08:24Another source indicated that this new romance was not a secret,
08:27and had become the talk of the Palm Beach social scene, saying,
08:30"'I guess they're not trying to hide it. They've been seen together all over Palm Beach.'"
08:35That Daily Mail report about Donald Trump Jr.'s shenanigans with Bettina Anderson
08:39reportedly hit Kimberly like the proverbial ton of bricks.
08:42However, insiders claimed that Don Jr. had hardly been low-key about his cheating,
08:47and that Kim had possibly even been turning a blind eye to her fiancé's dalliances.
08:51An insider told the outlet,
08:53"'Kimberly either didn't know about Bettina, or didn't want to know.'"
08:56Did she hear whispers that Don Jr. was fooling around with someone else? Probably.
09:00According to that source, discretion has never been Don Jr.'s strong suit. They added,
09:05"'He's pretty bold and, as smart as she is, Kimberly looked the other way.'"
09:09Despite the lack of shame with which her fiancé approached his new romantic relationship,
09:13Kimberly's future with Don Jr. remained an open question.
09:16The source pointed out that it was clear during the 2024 Republican National Convention
09:21that Kimberly's position within Trump-land had been marginalized,
09:24with her suddenly the odd woman out.
09:27Speculation about the state of the engagement between Don Jr. and Kimberly hit a fever pitch
09:32when President-elect Donald Trump took to social media to tweet his appointment of Kimberly as the
09:37United States ambassador to Greece. Given the rumors about Don Jr. and Bettina Anderson,
09:42and the simple fact that Kimberly had neither any connection to the country
09:46nor any experience whatsoever in international diplomacy, one key question arose immediately.
09:52Was Kim's appointment to Greece a way of getting her out of the way so that Don Jr. could pursue
09:56his new romance?
09:58"'I love President Trump. He is my great friend for over 20 years.'"
10:03If the ambassadorship was indeed a form of exile from Trump-land,
10:06Guilfoyle was savvy enough to put a different spin on it. She wrote on Instagram,
10:11"'As ambassador, I look forward to delivering on the Trump agenda,
10:14supporting our Greek allies, and ushering in a new era of peace and prosperity.'"
10:19Rumors that Kimberly and Don Jr. had booked one-way tickets to Splitsville seemed to
10:23solidify into fact when numerous sources came forward to confirm that they had ended their
10:28engagement and gone their separate ways. As one source told Page Six,
10:32the writing had been on the wall for some time. Don and Kimberly haven't been getting along over
10:36the past year. They get argumentative at Mar-a-Lago in front of people. Nothing crazy,
10:41but you know when a couple is fighting, they bicker in public.
10:44There may have been even more to the couple's breakup than that. A source told People,
10:48"'Don Jr. has always wanted to look good in his father's eyes.'"
10:51That source also went on to claim that Kimberly's stock within MAGA's inner circle had fallen
10:56significantly in recent months and that Don Jr. was anxious to prevent her from dragging him down
11:01with her. Don Jr. was allegedly on the hunt for another romantic partner who would help to elevate
11:06him in the eyes of his dad. Someone like Bettina, who is and has been a model and is in WASP-y
11:11circles of Palm Beach, is something that would impress him. Meanwhile, Don Jr.'s family is
11:16reportedly happy to see him put Kimberly in the rearview mirror, with the president-elect
11:20offering the ambassadorship as a smooth exit from Trump-land. A source told People,
11:24"'Kim is not a nice person and always wants the limelight. Don and Kim are over,
11:28but they are going to offer her some kind of an administrative position so she will be happy.'"