Donald Trump Jr. And Kimberly Guilfoyle Have Lived An Incredibly Lavish Life

Donald Trump Jr. and Kimberly Guilfoyle started dating back in 2018 and for a while, it looked like they were set to go the distance. Though Guilfoyle was already incredibly successful by the time she crossed paths with Donald Trump Jr., the two embarked on a relationship that gave "lavish" a whole new meaning.

Guilfoyle was welcomed into the family business, becoming an important fundraising official for Donald Trump's 2020 election campaign against Joe Biden. Guilfoyle's efforts were worthwhile, helping her once potential father-in-law win back the presidency in the 2024 election. With their combined fortunes, Guilfoyle and her beau lived it up in style throughout their relationship. They enjoyed everything from over-the-top vacations to VIP access at events, the best designer clothes, and much more.

Perhaps because of their shared joy for the finer things in life, fans were surprised when news spread of Kimberly Guilfoyle and Don Jr.'s split in December 2024. Donald Jr. wasted no time and quickly moved on, but Guilfoyle did get a consolation prize: a nomination for a U.S. ambassadorship. Let's take a walk down memory lane and recount just how wildly luxurious their time together really was — they certainly made the most of it! 

Just as Eric and Lara Trump live lavish lives, Donald Trump Jr. is able to live extravagantly, thanks to his considerable bank account. Donald Jr. is worth some $350 million, according to Celebrity Net Worth. He reportedly earned much of it while serving as executive vice president at his dad's company, the Trump Organization. He and his siblings Ivanka and Eric own a small percentage of the Trump International Hotel in Washington, D.C. Besides real estate and politics (Donald Jr. was a key member of his dad's two presidential campaigns), he's also a public speaker and a New York Times best-selling author.

Let's not forget that he's also in for a very healthy inheritance when the time comes. Though it's thought that Donald Trump's substantial fortune may have been impacted by his lengthy legal troubles, he's still got a lot of money in the bank. One day in the not-too-distant future, it's likely that a good chunk of his estate will fall to his sons and daughters.

Donald Trump Jr. and Kimberly Guilfoyle didn't have to suck it up in coach, thanks to their White House connections. They preferred to fly private, but living life lavishly sometimes comes at a cost.

Trump and Guilfoyle hopped on a private flight home to New York from South Dakota in the summer of 2020, after Guilfoyle contracted COVID-19. What a privilege, especially when Guilfoyle's junior campaign staffers were reportedly forced to quarantine in South Dakota due to their close proximity to her.

Guilfoyle also made use of private planes to get to and from fundraisers and rallies during the 2020 presidential campaign. According to The New York Times, there were so many requests for private flights by her fundraising team that "the campaign had to work out a plan for approving such trips, which must be listed as in-kind contributions or reimbursed by the campaign." Although Guilfoyle's flights didn't go against any laws, it was also reported by the Times that a couple of her aides took a private flight for a fundraising event without seeking approval. 

Luckily for Guilfoyle, she had Air Force One as an alternative when a private jet wasn't available.

In 2019, most of the Trump family got together to celebrate Kimberly Guilfoyle's 50th birthday. The milestone day was celebrated with a fancy dinner and custom birthday cake at New York City's Omar at Vaucluse (where many celebrities dine). And that was apparently just an appetizer for what was to come. The birthday festivities reportedly continued down at Donald Trump's Mar-a-Lago resort in Palm Beach, Florida. There, Kimberly was serenaded by former Pussycat Dolls singer Kaya Jones. A source told People that the Mar-a-Lago party was "designed to give Kimberly a great day at the club."

For Donald Trump Jr.'s birthday the year prior, the couple dined at the Trump National Golf Club in Jupiter, Florida. As Trump shared on Instagram, the then-couple enjoyed a chocolate mousse dessert and chocolate-covered strawberries. These two surely know how to celebrate a birthday.

Getting to go backstage at big-name concerts can be hard to come by for us regular folk, but there's nothing regular about Donald Trump Jr. and Kimberly Guilfoyle. In 2018, the then-couple not only enjoyed front row access at a Poison concert at Long Island's Jones Beach Theater, but they also met the rock band's lead singer, Bret Michaels. In an Instagram post, Trump dubbed Michaels a "good friend." He continued, writing, "You can't find a cooler group of guys who love their fans and do so much for our vets. Great show last night on Long Island."

On another occasion, Trump and Guilfoyle got a chance to meet Kid Rock. This time, however, it wasn't backstage access. The country-rock singer was performing at a 2020 campaign event hosted by Trump and Guilfoyle in support of Donald Trump Sr.

Kimberly Guilfoyle has had a stunning transformation, having already lived quite well before linking up with Donald Trump Jr. During her days as a Fox News host, she owned a $3.5-million apartment in Manhattan. The luxurious pad featured a dreamy walk-in closet perfect for the fashionista.

"Every girl knows you can never have enough closet space. And in New York City, wow it's like you need a magic wand to figure it out. I tried to make sure to maximize every inch of space," Guilfoyle told Us Weekly during an interview in which she walked the outlet through the space. Yes, her closet deserved its own feature. 

With floor-to-ceiling shelves for designer accessories, including jewelry, purses, and an estimated 500 pairs shoes, Guilfoyle's closet is a dream for most of us. Not to mention, the items inside her closet were designed by big names like Valentino and Alexander McQueen.

When they weren't hard at work, Kimberly Guilfoyle and Donald Trump Jr. knew how to have fun. That was especially true when they were guaranteed the best seats in the house.

During the 2020 Super Bowl, Guilfoyle and Trump were spectators in their own private box. At the halftime show, when Jennifer Lopez and Shakira took over the stage for their awe-worthy performance, Guilfoyle was clearly enjoying herself, as she was seen dancing along to some of the famous tunes as her boyfriend reportedly said, "Come on, baby!" They were joined by other Trump family members, including Trump's brother, Eric, and his wife, Lara. 

Guilfoyle took to Instagram with a photo of herself and Trump by the window overlooking the football field below. In the caption, she wrote that she was "born and raised in San Francisco" and was rooting for the 49ers, but unfortunately not even those who lead the most lavish lives can get everything they want, as the Kansas City Chiefs took home the win.

Donald Trump Jr. and Kimberly Guilfoyle certainly knew how to enjoy a lavish vacation. In 2018, the outdoorsy duo spent time in Montana fly fishing and enjoying life on a secluded river. Trump enjoyed their Montana getaway so much that he shared a glimpse of their vacation on Instagram, detailing their time on the Stillwater River. Besides fishing, they also did some target practice.

Don Jr. and Guilfoyle didn't shack up at chain hotels when they traveled together, of course. In fact, they loved staying at pricey spots — the more expensive, the better. Their approximately $64,000 trip to Paris included staying at a hotel with a cost of $1,000 per night, according to U.S. Secret Service records obtained by HuffPost. About $23,000 was spent on hotel rooms alone during the two-day trip, and roughly $31,000 was spent on air travel. Trump and Guilfoyle also visited Monaco during their stay, although the documents didn't detail the costs of that trip.

Expensive hotel stays are on brand for the Trump family. During Donald Trump Sr.'s state visit to London, he brought along his adult children, including Donald Trump Jr., and more than $1 million was reportedly spent on their stay at the InterContinental hotel in Mayfair, according to The Guardian. Yes, you read that right. The walls of the hotel must be made of gold.

Being the celebrities they are, Donald Trump Jr. and Kimberly Guilfoyle are treated as such, especially when they made public appearances together. Typically, the red carpet is rolled out with a nice paycheck to boot. During a keynote presentation at the University of Florida in 2019, the then-couple received $50,000 for their appearance, according to The Gainesville Sun. That's an entire year's salary for many people. The money reportedly came from student activity fees, which is part of the tuition. 

This five-figure speech was far from the only one Donald Trump Jr. has been paid to do. According to NBC News, he was paid anywhere up to $100,000 for a string of public speeches he made in 2017 at foreign events and at schools, both private and public, while his father was in office. These were not considered ethic violations, as he did not work in the White House. 

In addition to being paid for public appearances, Kimberly Guilfoyle received a pretty penny for solo speeches. While it's not like she desperately needs the cash that comes from speaking at public events, every little (or lot) surely helps.

A committee member told CNN that Guilfoyle was reportedly paid $60,000 for a short speech introducing Donald Trump at a 2021 rally in Washington just days before he was set to hand over the White House to the new president, Joe Biden. While Guilfoyle pocketed the funds, there was a backlash when insiders later revealed the fee came from money donated to the Trump campaign. "These weren't rich people," representative Zoe Lofgren of California told CNN (via Yahoo! News). "They were conned by the president. It was a big lie and it was also a big rip-off." 

Guilfoyle's speech has also come under fire for seemingly encouraging the Capitol Hill riots, as she told crowds, "We will continue to stand for President Trump, stand with him and for this country. We will not allow the liberals and the Democrats to steal our dream or steal our elections." Despite the furor afterward, Guilfoyle has never mentioned the payment. 

Rich people love to buy houses. We see it in the news all the time. Dropping millions of dollars on a home is nothing when the balance of your bank account ends in a long string of zeroes, and the Trump family's homes are nothing if not luxe.

Back in 2021, Kimberly Guilfoyle and Donald Trump Jr. bought a sprawling property in Jupiter, Florida, a stone's throw away from Donald Trump's Mar-a-Lago estate. Worth around $15 million, the gorgeous waterfront property boasts an impressive 11,300 square feet of living space and was allegedly where Guilfoyle healed her broken heart after the two parted ways, according to the Daily Mail. Although, there was arguably enough room for both of them to be there.

The property has 11 bedrooms, so if they wanted to avoid each other, it would've been easy enough to do. The couple were reportedly drawn to the sheer size of the home, which sits on a piece of land considerably larger than the average property in the area. At the time of this writing, the former flames have yet to put the house on the market. If they do, they would undoubtedly see a sizable return on investment, as they paid just $9.7 million for it, substantially less than the current estimated value.

After a few years of dating, Donald Trump Jr. and Kimberly Guilfoyle's relationship got even more serious. Don Jr. popped the question in 2020, though the news wasn't made public until nearly 2022, the Daily Mail reported. It seemed like the fairytale was just beginning, thanks in part to the enormous rock on Guilfoyle's finger.

The stunning sparkler was a huge diamond that suited Guilfoyle's aesthetic down to the ground and, as you might expect, it wasn't cheap. Though the couple never talked about the price of the piece publicly, a diamond expert weighed in on Kimberly Guilfoyle's ring in an exclusive interview with The List.

Olivia Landau, founder and CEO of The Clear Cut, told us, "It looks like an emerald cut, perhaps around 5 carats. It looks like there may be trapezoid side stones." According to the pro, a rock of that size can cost anywhere in the region of $65,000 to $250,000. The Trump men rarely go for cheap options, so it's not a stretch to assume this ring was on the higher end of the spectrum. Whether Guilfoyle opted to give it back post-split is unknown. 

Some couples break up and opt to avoid each other for the rest of their days, but Donald Trump Jr. and Kimberly Guilfoyle may find that a little tricky. Their romance may have ended, but when Donald Trump won the 2024 election, he nominated his son's former love a job in the Department of State as the ambassador to Greece. The news of Guilfoyle's swanky nomination broke shortly after Trump's election victory in December 2024. Taking to Truth Social, the new president stated, "For many years, Kimberly has been a close friend and ally. 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." 

For her part, Guilfoyle said she was honored to be put forward for such a prestigious position, which has to be approved by the Senate before being made official. This new appointment would mean a lot of traveling for Guilfoyle and it comes with the use of a stunning mansion in Athens, Greece, called Jefferson House. The building is set among plush greenery in an upscale part of the city. 

Looking back at photos of Kimberly Guilfoyle and Donald Trump Jr. taken at the start of their relationship in 2018, it's hard to imagine that they wouldn't end up together. However, in late 2024 rumors began to circulate that they had called things off. Don Jr. confirmed the news in a December statement released to Page Six. "Kimberly and I will never stop caring for each other and will always keep a special bond," he explained. "I could not be more proud of her and the important role she'll continue to play in my father's administration."

Despite the niceties, Guilfoyle and Don Jr.'s breakup was likely messier than it seemed, as their shared lifestyle was altered after their split. For one, Guilfoyle faces a new life in a foreign country without their sprawling Florida mansion and the perks that come with being an official part of the Trump family. While fancy vacations together and joint speaking engagements may be a thing of the past, Donald Jr. doesn't appear to be suffering much after the split, having already moved on with a new love, Bettina Anderson. Anderson began to enjoy the Trumps' hospitality quickly, spending New Year's Eve with her beau and his family at the Mar-a-Lago estate. 

A source told People that Trump had been seeing Anderson for months, but "for the most part, Kim has looked the other way because she loves the power and lifestyle." Anderson comes from a very wealthy background herself, so Guilfoyle may find herself on the losing end of this situation. 

Although Donald Trump Jr.'s net worth is significantly higher than his ex's, Guilfoyle's is nothing to sneeze at. Thanks to her professional pursuits over the years, Kimberly Guilfoyle is worth an estimated $25 million, according to Celebrity Net Worth. She had a career as a prosecutor before making her way up to deputy district attorney in Los Angeles. It takes a lot of determination and tenacity to go as far as Guilfoyle has. Let's not forget that she was also a successful television personality, co-hosting shows like "The Five" and "Outnumbered" as well as other Fox News programs. Guilfoyle was also previously married to politico Gavin Newsom, although it's not clear if she received a settlement when they parted ways. 

Guilfoyle's career doesn't seem to be slowing down after her split from Donald Trump Jr., either, thanks to her appointment in the Trump administration. According to Chron, U.S. ambassadors' salaries can earn as much as the vice president of the United States, — a salary of $235,100. That's one heck of a paycheck, and it will undoubtedly earn Guilfoyle some nice interest on her already excessive bank account.