Inside Kimberly Guilfoyle’s rollercoaster relationship with the Trumps from ‘promenade king and queen of MAGA land’ romance with Don Jr to their ‘break up’ and her new envoy job in Greece

Fox News host turned overseas ambassador, Kimberley Guilfoyle has lived many lives, but all roads appear to lead back to the Trumps.

Beginning as early as 2007, Guilfoyle was running in the same circles as the Trumps, crossing paths at glitzy events and sending her son to the same private school as her future-fiance.

Over a decade later, the former district attorney became a conservative influencer and adviser to President-elect Donald Trump while embarking on a sensational romance with his eldest son.

Once dubbed the ‘prom king and queen of MAGA land’ the 55-year-old, alongside Donald Trump Jr. grabbed headlines throughout Don’s 2024 election campaign as they stood united and set to wed.

The pair bolstered Trump’s presidential run with primetime addresses at the National Convention in July and appeared arm-in-arm at rallies across the States but the political love-story would eventually come to a screeching halt.

In December DailyMail.com revealed the power couple’s wedding was called off amid a rollercoaster cheating scandal, with Guilfoyle left ‘blindsided’ by photos of her beau with Palm Beach ‘it girl’ Bettina Anderson.

But before she could even respond to the claims, President-elect Donald Trump would swoop in with a political job offer too good to refuse. 

After almost two decades of relationships with the Trump family – both professional and romantic – Guilfoyle is now set to serve as US ambassador to Greece in her latest career twist.   

2007

Guilfoyle and Trump Jr. were first spotted at events together in New York City in 2007 and 2008 – but at the time, they were both in different relationships.

From 2001 to 2006, she was first lady of San Francisco while married to Democratic politician Gavin Newsom during his time as mayor.

The high-profile political couple were once dubbed ‘the new Kennedys’. 

After they divorced, Guilfoyle married businessman Eric Villency in 2006 and the pair had a son together the following year before splitting in 2009.

Trump Jr. had married model Vanessa Haydon in 2005, but the pair divorced in March 2018 and share five children. 

But Guilfoyle and the Trumps have run in the same circles for years, beyond the parties and glam events, with her son Ronan, and Don Jr.’s oldest daughter, Kai, attending the same Manhattan private school. 

2017

The Fox News host revealed she was in conversation with the Trump administration about becoming White House press secretary.

Guilfoyle said the idea of her taking the job or another press role in the White House had been ‘raised by a number of people’ in the Trump administration.

‘I’m a patriot, and it would be an honor to serve the country,’ Guilfoyle told The Mercury News at the time. 

‘I think it’d be a fascinating job. It’s a challenging job, and you need someone really determined and focused, a great communicator in there with deep knowledge to be able to handle that position.’ 

She was originally considered for press secretary during the presidential transition, but the job was offered to Sean Spicer, the former spokesman for the Republican National.

On her show, she said: ‘If you want to be successful and do communications with President Trump, you have to be someone who he actually wants to spend a little bit of time with.

‘You’ve got to insist on getting in front of POTUS, talk to him, and have like five, six minutes with him before you go out there and take the podium, and otherwise you’re driving blind.

‘It has to be somebody with a very close relationship, where there’s trust there, there’s inherent loyalty, someone who’s been there from the beginning,’ she added.

As part of a later interview, Guilfoyle said she thought she had that kind of relationship with Trump. 

She’s said she’s known Trump and his family for more than a decade – with the pair first meeting at charity events when she moved to New York in around 2004 to start a TV career.

‘I think I have a very good relationship with the president,’ Guilfoyle said. 

‘I think I enjoy a very straightforward and authentic, very genuine relationship, one that’s built on trust and integrity, and I think that’s imperative for success in that position’.

2018 

Three months after Trump Jr.’s wife Vanessa filed for divorce, reports began swirling that he and Guilfoyle were dating.

In the same year, the Fox News host quit her job amid sexual harassment allegations, for which the network paid her former assistant a multimillion-dollar settlement.

Guilfoyle then joined the pro-Trump super PAC America First Action.

Don Jr. and Guilfoyle began dating in April 2018, where they reportedly made their debut as a couple at a send-off party for the Trump administration’s ambassador to Germany, Richard Grenell.

The new pair made their relationship Instagram official in June, after he shared an image of them both smiling together with Bret Michaels from the band Poison.

In the same month, Trump Jr. thanked his ‘significant other’ in his convention speech during the Montana Republican Convention.

‘We’re going to take her fishing tomorrow, then shooting,’ he said. 

‘This is a miniature test to see if she really likes it, or if she’s going to pretend to like it, but either way we’re going to have a good time — or at least I will.’ 

Their relationship continued to blossom in the public eye, with the couple overheard calling each other pet names during a week in Southampton, New York, Page Six reported.

Guilfoyle reportedly called Trump Jr. ‘Junior Mint,’ which Page Six speculated was a reference to his bank account, and Trump Jr. dubbed Guilfoyle ‘Pooh Bear.’ 

2019

After joining the Trump campaign as a senior advisor in April, Guilfoyle made several appearances at rallies across the states, alongside her new beau.

She spoke at a rally at the Williamsport Regional Airport in Montoursville, Pennsylvania, in May 2019, and Trump’s 2020 campaign kick-off rally in Orlando that June.

‘She’s definitely made Don Jr. more serious,’ R. Couri Hay, a New York publicist, told Business Insider. 

‘She’s had years and years on TV. She’s helped guide and train and been very influential in Don’s increasingly very secure, very formidable, very opinionated television personality. 

‘They are like the prom king and queen of MAGA land,’ a senior Trump advisor told the publication.

Another former Fox News colleague said: ‘It’s interesting to me that Donald Trump Jr. ended up with a female version of his father’.

Guilfoyle impressed the president so much in her advisory role that he went on to personally ask her to lead the fund-raising effort for Trump Victory.

‘A lot of the professional fundraisers thought she was just being given a title and were very skeptical, and she’s been an animal,’ Spicer said. 

‘She is tenacious when she comes to raising money.’ 

2021

After two years of supporting her partner and his father during events and TV shows and packing on the PDA in public, the couple skipped President Joe Biden’s January inauguration and began looking for homes in Florida.

When they arrived in Palm Beach, the pair began searching for waterfront homes in Admirals Cove, a gated community in Jupiter.

They were reportedly in contracts to purchase an $11million seven-bedroom, 12-bathroom home, with Guilfoyle also looking at the $9.5million two-story home next door that featured six bedrooms and 11 bathrooms.

Two months later the couple sold their 9,200sq ft Bridgehampton home for $8million and purchased a $9.7million home in Admirals Cove, about 20 minutes from Mar-a-Lago.

2022

Reports began swirling that the coupe had gotten engaged after Guilfoyle posted an image on Instagram where she appeared to be wearing a diamond ring.

‘Tonight was extra special celebrating donaldtrumpjr’s birthday,’ Guilfoyle captioned the photo.

‘Don, you are strong, smart, courageous, funny and the love of my life. I can’t wait to spend the rest of our lives together. Love you.’

In February, Guilfoyle confirmed their engagement, calling Don Jr. her fiance on a Valentine’ Day Instagram post.

Eight months later, she attended Trump’s 2024 campaign launch event alongside Eric Trump, Lara Trump, and Jared Kushner.

2024

Don Jr. and Guilfoyle marked their six-year anniversary in April, with the loved-up man writing on Instagram: ‘Thanks for always being there no matter what the haters are throwing our way, I love you.’

Presenting a united front that seemed stronger than ever, the couple in July spoke during the third night of the Republican National Convention.

But just five months later, the whirlwind engagement was called off.

Guilfoyle was left ‘blindsided’ by photos of her fiance enjoying an intimate brunch with another woman in September, before the couple split in December, DailyMail.com exclusively revealed.

According to one source familiar with the family: ‘There is no more Kimberly and Don – at least not romantically. Their engagement hasn’t officially been called off yet. They were waiting until after the inauguration to announce.’

And while Kimberly, 55, hasn’t been seen with Don Jr., 46, for weeks, he has been spending an increasing amount of time with Palm Beach socialite and ‘it girl,’ Bettina Anderson – the new woman in his life about whom he is said to be ‘crazy.’

The source said: ‘The truth is Don and Bettina are still very much together. He’s crazy about her.’

DailyMail.com first exposed his romance with the 38-year-old blonde when the pair were seen together canoodling over brunch in Palm Beach towards the end of the summer.

As a consolation prize, President-elect Trump made Guilfoyle the ambassador to Greece.

‘For many years, Kimberly has been a close friend and ally,’ Trump, 78, posted on Truth Social.

‘Her extensive experience and leadership in law, media, and politics along with her sharp intellect make her supremely qualified to represent the United States, and safeguard its interests abroad,’ the president-elect added.

Guilfoyle said Tuesday that she was ‘honored to accept’ Trump’s nomination, which requires Senate approval. 

‘I’m honored to accept President Trump’s nomination to serve as the next Ambassador to Greece and I look forward to earning the support of the U.S. Senate,’ she wrote on X. 

‘President Trump’s historic victory is bringing hope and optimism to the American people and to freedom-loving allies across the world.’

‘It was the democratic values born in Greece that helped shape the founding of America,’ Guilfoyle added. 

‘And now, we have an opportunity to honor that history by bringing better days here at home and abroad.’

‘As ambassador, I look forward to delivering on the Trump agenda, supporting our Greek allies, and ushering in a new era of peace and prosperity.’