Fox News host turned ambassador, Kimberly Guilfoyle, has experienced many phases in her life, yet it seems all paths lead back to the Trumps.
Starting as early as 2007, Guilfoyle mingled in the same circles as the Trumps, attending glamorous events and enrolling her son in the same private school as her future fiancé.
More than a decade later, the former district attorney emerged as a conservative influencer and advisor to President-elect Donald Trump while embarking on a high-profile romance with his eldest son.
Once referred to as the “prom king and queen of MAGA land,” the 55-year-old and Donald Trump Jr. made headlines during Don’s 2024 election campaign, appearing united and preparing for marriage.
The couple supported Trump’s presidential bid with prime-time speeches at the National Convention in July and were seen together at rallies across the country, but their political love story ultimately came to an abrupt end.
In December, DailyMail.com reported that the couple’s wedding plans were canceled amid a tumultuous cheating scandal, leaving Guilfoyle “blindsided” by photos of her partner with Palm Beach socialite Bettina Anderson.
Before she could address the situation, President-elect Donald Trump stepped in with an irresistible political job offer.
After nearly two decades of connections with the Trump family—both personal and professional—Guilfoyle is now poised to take on the role of U.S. ambassador to Greece in this latest chapter of her career.
Donald Trump Jr. and Kimberly Guilfoyle stood alongside President Donald Trump at a rally held at the Crown Expo Center in Fayetteville, North Carolina, on the evening of September 9, 2019.
Guilfoyle and Trump Jr. were first seen together at events in New York City in 2007 and 2008, though they were both in separate relationships at that time.
From 2001 to 2006, she served as the first lady of San Francisco while married to Democratic politician Gavin Newsom during his tenure as mayor. The couple was often referred to as “the new Kennedys.”
After their divorce, Guilfoyle married businessman Eric Villency in 2006, and they welcomed a son the following year before parting ways in 2009.
Trump Jr. was married to model Vanessa Haydon in 2005, but they divorced in March 2018, sharing five children together.
However, Guilfoyle and the Trumps have been intertwined in the same social circles for years. Beyond glamorous parties, her son Ronan and Don Jr.’s oldest daughter, Kai, attended the same private school in Manhattan.
Richard Turley, Donald Trump Jr., Vanessa Trump, Eric Villency and Kimberly Guilfoyle attend the Inocente Tequila Tasting on June 17, 2008 at a private residence in New York
Gavin Newsom at home with his then-wife, Kimberly Guilfoyle. From 2001 to 2006, she was first lady of San Francisco while married to the Democratic politician during his time as mayor
Former U.S. President Bill Clinton (L) speaks at a campaign rally for San Francisco mayoral candidate Gavin Newsom (C) as Guilfoyle (R) looks on December 8, 2003
Guilfoyle married businessman Eric Villency in 2006, and they welcomed a son the following year before their separation in 2009.
In 2017, the Fox News host disclosed that she was in discussions with the Trump administration about the possibility of becoming White House press secretary. She mentioned that the idea of her taking on this role had been suggested by several individuals within the administration.
“I’m a patriot, and it would be an honor to serve the country,” Guilfoyle told The Mercury News at the time. She expressed that the position would be fascinating and challenging, requiring someone determined, focused, and a great communicator with in-depth knowledge.
Initially, she was considered for the press secretary role during the presidential transition, but the position ultimately went to Sean Spicer, the former spokesman for the Republican National Committee.
On her show, she remarked, “To succeed in communications with President Trump, you need to be someone he wants to spend time with. You have to make sure to get in front of him for a few minutes before taking the podium; otherwise, you’re driving blind.”
She emphasized the importance of having a close relationship built on trust and loyalty. In a later interview, Guilfoyle stated that she believed she shared that kind of relationship with Trump, having known him and his family for over a decade since they first met at charity events after she moved to New York in 2004 to pursue a television career.
“I believe I have a very good relationship with the president,” Guilfoyle said. “It’s straightforward, authentic, and genuine, built on trust and integrity, which is crucial for success in that role.”
David Zinczenko and Kimberly Guilfoyle attend the Galvanized Media Holiday Party and Dave Zinczenko’s birthday celebration at private residence on December 12, 2017
Guilfoyle was seen at a New York City gala in 2017 after announcing that she was in talks with the Trump administration about the role of White House press secretary.
In 2018, just three months after Trump Jr.’s wife Vanessa filed for divorce, rumors began to circulate about his relationship with Guilfoyle. That same year, the Fox News host left her position amid sexual harassment allegations, leading to a multimillion-dollar settlement for her former assistant.
Following this, Guilfoyle became involved with the pro-Trump super PAC America First Action.
Don Jr. and Guilfoyle started dating in April 2018, reportedly making their public debut as a couple at a send-off party for Richard Grenell, the Trump administration’s ambassador to Germany.
They made their relationship Instagram official in June when Trump Jr. shared a photo of them smiling alongside Bret Michaels from the band Poison. During the same month, he expressed gratitude to his “significant other” in his speech at the Montana Republican Convention, stating, “We’re going to take her fishing tomorrow, then shooting. This is a miniature test to see if she really likes it or if she’s just pretending, but either way, we’re going to have a good time — or at least I will.”
Their romance continued to flourish in the public eye, with reports of the couple using pet names for each other during a week spent in Southampton, New York. Guilfoyle affectionately referred to Trump Jr. as “Junior Mint,” which Page Six speculated might relate to his finances, while he called her “Pooh Bear.”
Don Jr. and Guilfoyle began dating in April 2018. Pictured: Donald Trump, Jr. and Kimberly Guilfoyle attend the DC premiere of the film, ‘Death of a Nation,’ at E Street Cinema on August 1, 2018 in Washington
Guilfoyle and Donald Trump Jr. are seen at a Ted Cruz Rally at the Lone Star Convention Center on October 3, 2018 in Conroe, Texas
Trump Jr. and Kimberly Guilfoyle at a campaign rally in support Montana Senate candidate Matt Rosendale in Bozeman, MT on September 25, 2018
Take a look back at the relationship of Don Jr. and Kimberly Guilfoyle
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 at 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 has years of experience on TV. She’s helped guide, train, and has been very influential in Don’s increasingly secure, formidable, and opinionated television personality.”
“They are like the prom king and queen of MAGA land,” a senior Trump advisor remarked.
Another former Fox News colleague noted, “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 personally asked her to lead the fundraising effort for Trump Victory.
“A lot of the professional fundraisers thought she was just being given a title and were very skeptical, but she’s been an animal,” Spicer said. “She is tenacious when it comes to raising money.”
Trump Jr. and Guilfoyle appeared on November 7, 2019 on ABC’s ‘The View,’ as the show celebrated its 5,000th episode
Guilfoyle spoke alongside her beau during a rally with President Donald Trump at the Williamsport Regional Airport in Montoursville, on May 20, 2019
Donald Trump, Jr hugs his girlfriend, Kimberly Guilfoyle, before speaking at the University of Florida in October 2019
Senior adviser Jared Kushner, Ivanka Trump and Kimberly Guilfoyle, watch as President Donald Trump speaks at his re-election kickoff rally at the Amway Center, on June 18, 2019
Don Jr’s fiancee Kimberly Guilfoyle gives fiery speech at convention
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.
The couple packed on the PDA in August 2020 during the Sportsmen for Trump Launch in Coplay
Trump Jr. (R) watches his girlfriend Kimberly Guilfoyle as she pre-records her address to the Republican National Convention at the Mellon Auditorium on August 24, 2020 in Washington
Donald Trump Jr., Kimberly Guilfoyle and Eric Trump exit Air Force One at the Palm Beach International Airport on the way to Mar-a-Lago Club on January 20, 2020 in West Palm Beach
Trump, Jr. and Kimberly Guilfoyle stand on stage as they address the Conservative Political Action Conference being held in the Hyatt Regency on February 26, 2021 in Orlando
The pair sold their 9,200sq ft Bridgehampton home (pictured) 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.
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 (pictured)
Kimberly Guilfoyle, Jared Kushner, Eric Trump, and Laura Trump listened as former US President Donald Trump spoke during an event at his Mar-a-Lago home on November 15, 2022, in Palm Beach.
2024
Don Jr. and Guilfoyle celebrated their six-year anniversary in April, with Don Jr. expressing his affection 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 spoke during the third night of the Republican National Convention in July. However, just five months later, their whirlwind engagement was called off.
Guilfoyle was reportedly “blindsided” by photos of her fiancé enjoying an intimate brunch with another woman in September, leading to their split in December, as revealed exclusively by DailyMail.com.
According to a 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.”
While Kimberly, 55, hasn’t been seen with Don Jr., 46, for weeks, he has been spending increasing 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 added: “The truth is Don and Bettina are still very much together. He’s crazy about her.”
DailyMail.com first reported on his romance with the 38-year-old blonde when they were spotted together canoodling over brunch in Palm Beach towards the end of the summer.
As a consolation prize, President-elect Trump appointed Guilfoyle as the ambassador to Greece. “For many years, Kimberly has been a close friend and ally,” Trump, 78, posted on Truth Social.
Guilfoyle and Donald Trump Jr., son of former US President Donald Trump, attend the first day of the Republican National Convention at the Fiserv Forum on July 15, 2024 in Milwaukee
Family members: Michael Boulos, Tiffany Trump, Kimberly Guilfoyle, Donald Trump Jr., Kai Trump, Donald Trump III, Eric Trump) and supporters of Donald Trump stand on stage during Trump’s Election Night Watch Party at the Palm Beach County Convention Center November 5, 2024
She appeared with other members of the Trump family in their box at the Republican National Convention in Milwaukee, Wisconsin, in July
These exclusive DailyMail.com photos are the most compelling evidence to date that Donald Trump Jr. has moved on with new Palm Beach ‘it girl’ Bettina Anderson
A photo obtained exclusively by DailyMail.com shows Don Jr. having brunch with Palm Beach socialite Bettina Anderson, 37, in mid August – with fiancée Kimberly Guilfoyle nowhere in sight
“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 stated on 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.”
