The Shady Side Of Kathy Hilton

We know Kathy Hilton more for her famous daughter, Paris Hilton, than the hotel chain, but Kathy has a really interesting story of her own. She hailed from the vivacious Kathleen Richards, mother also to Kyle Richards and Kim Richards, who had a remarkable reputation, and if we had any doubt that she was larger than life, just note that her nickname was "Big Kathy."

In the notable book "House of Hilton" by Jerry Oppenheimer, the author explains how Big Kathy urged her three daughters to marry for money and do whatever was needed to make this happen. Syliva Richards, who married Big Kathy's former husband, said that the matriarch had a man teach Kathy how to please men sexually, since this was forefront in Big Kathy's advice for landing a rich man. Big Kathy certainly achieved her goal, since all three of her daughters became famous in their own ways. Kathy, of course, married into the Hilton family, while Kyle and Kim were long-time familiar faces of "The Real Housewives" franchise. Kathy also graced the screens of Bravo. But this level of success came with a degree of cut-throat boldness.

Sylvia told Oppenheimer that Big Kathy didn't care. "She believed that rules didn't pertain to her," Syliva said of her husband's former wife. "And this is the way she brought up the girls. There were no rules for them, either. And that's the way Kathy brought up Paris." Well, clearly the drive for success worked, but not without developing a shady side.

If we've observed anything about the Hilton family, it's that they don't have a reputation for passing on the lion's share of the inheritance to their children. Founder Conrad Hilton famously left nearly all of his fortune to the Conrad N. Hilton Foundation when he died in 1979, according to Reuters.

Son Barron Hilton didn't get any kind of special treatment (or inheritance!) from Conrad. As Forbes notes, Barron started his career as an elevator operator in one of his dad's hotels but he eventually took over the empire and subsequently took home $800 million in 2007 after selling the Hilton Hotels to Blackstone, a private equity firm. Despite getting the short end of the stick from his own dad, Barron did the same thing and "pledged" 97% of his fortune to, you guessed it, the Conrad N. Hilton Foundation, despite having eight children of his own.

So, for son Richard Hilton, he faced the same tough love that seemed to be passed along in the Hilton family. Instead of focusing the attention on Richard, son Steven Hilton became the president of the foundation, per Reuters. But some of the decision to overlook Richard was because the family saw Kathy Hilton as too much of a wild card and far too eager to share in the Hilton family. In "House of Hilton," Jerry Oppenheimer quoted Barron saying of Richard: "If he can't control his wife, how can he run my hotels?" So, Kathy was a part of Richard's demotion within the family brand.

Richard and Kathy Hilton had four children: Paris, Nicky, Barron, and Conrad, per The U.S. Sun. By all accounts, they looked like a happy family, but in-laws and relatives later spoke about the fact that Kathy used hired help and relatives too frequently, shuffling off child care on others.

Barron Hilton's brother, Eric Hilton, was first married to Patricia Skipworth Hilton and this woman had a lot to say about Kathy's mothering in the book "House of Hilton." Patricia said, "Here comes Kathy with Paris, who was nine months old and a great big, fat, pretty baby." Kathy asked Patricia if she wanted to hold Paris and the next thing she knew, Kathy was long gone. "She took off until that evening," Patricia said of Kathy. "I wanted to kill her! She didn't leave any instructions on what time Paris had to be fed. There weren't any diapers. She just left me in the lurch."

Richard's mother, Marilyn Hilton, ran into Patricia in the midst of this and said, "Well, I guess you're it for the day. Kathy does this all the time. She just wants to go out, and she knew you'd take care of the kid." Needless to say, some Hilton relatives weren't too impressed with Kathy's lackadaisical attitude towards babysitting.

Kathy Hilton had aspirations to be famous. Her longtime friend Nikki Haskell told Vanity Fair, "Of course Kathy wanted to be a star. Who didn't?" This was logical since her mother, Big Kathy, hammered it into her daughters that wealth and success were the ultimate goals in life. For Kathy, stardom didn't come the way she expected it would. Jerry Oppenheimer wrote in "House of Hilton" that Kathy transposed these ambitions onto her children, especially Paris Hilton. Patricia Skipworth Hilton said that Kathy called Paris "'Star' from day one."

Both Kathy and her mother, Big Kathy, were obsessed with Paris and determined that she would be famous. Big Kathy used to call her granddaughter "my Marilyn Monroe" and told young Paris that she would be even more famous than the cultural icon. The duo tried to make Paris a child model, so the young woman certainly had a script written out for her life before she got a chance to agree.

Author Oppenheimer said that the experience of writing "House of Hilton" changed his view of Paris, in light of how she was mothered. "I came away with sympathy for Paris," he said, according to Vanity Fair. "When she was a kid she thought about becoming a veterinarian. But she had no chance to do anything but what she has done." In fact, the outlet notes that Paris lost interest in becoming a veterinarian when she discovered that she could satisfy the desire for animal contact by buying them, instead.

Conrad Hilton was famous for his work ethic and his shrewd entrepreneurial spirit. In the first hotel he ever bought, he slept in the office along with his business partner so that every bed on the premises could be used for a profit, per the Archbridge Institute. He hated wasted space and chose smaller front desks so that he could put up shops in the front lobbies of his hotels. This spirit was carried down, even when the Hilton chain became an empire, and part of this austerity meant that Hilton family members were never given special treatment in the hotels. However, as Jerry Oppenheimer writes in "House of Hilton," there was one person who tried to override this tradition as often as possible: Kathy Hilton.

A manager at the time told Oppenheimer that Richard Hilton first demanded a special suite and then called for various comforts. "We like a nice California red wine and something white," Richard allegedly began, "and my wife likes seafood." Then, unsurprisingly, they asked for childcare. "And then he demanded a babysitter," the manager said. "I had to convince the hotel's elderly German seamstress to do the sitting."

At other hotels, the same thing happened. One hotel employee said that "the spotlight always had to be on Kathy." Allegedly, if she didn't get her way, she would say, "Do you know who we are? Do you know who I am?" Hotel staff had a habit of running the other way when they saw her coming.

Kathy Hilton often had a reputation for being overly demanding and entitled, especially towards staff and since they were always in hotels, much of her bad behavior was retold by the Hilton employees. Peggy Yakovlev, a former Hilton hotel staff member, told Jerry Oppenheimer for "House of Hilton" that Kathy and hubby Richard Hilton set a bad tone for their kids. "Kathy and Rick and the girls looked down their noses at the help and were very judgmental," she said. "Paris and Nicky were running loose in the hotel, were always trouble, and the mother always seemed to be coaching them."

Yakovlev said that "Kathy was absolutely pushy, arrogant, condescending, and presumptuous, and Paris picked that up from her." Yikes! The sentiment was echoed by Patricia Skipworth Hilton, who told Oppenheimer: "Kathy Hilton's very selfish and very spoiled and very self-centered, and that absolutely carries through to Paris." There were endless reports from hotel staff about the struggles of dealing with this one particular group of Hiltons, and based on their accounts, the apples didn't fall far from the tree. 

The most widely known factoid about the Hilton family is Paris Hilton's time at the Provo Canyon boarding school in Utah, where she was sent in 1996, per Hello! The experience was traumatizing for Paris and it altered her relationship with her parents, especially her mother, Kathy Hilton. On an episode of "Paris in Love," the star said, "At Provo, I was stripped of all of my human rights, cut off from the outside world, so I wasn't able to speak to my parents for months."

The silence seemed to be an ongoing theme. Later, when Paris released her 2020 documentary "This is Paris," Kathy didn't know what was coming. When asked by Bustle if Kathy knew much about the project, she said, "No, but she's always doing something, so it's hard for me to keep up." The next question was the big one. Did Kathy know about Paris' experience at Provo? "No," Kathy answered. "I don't think at that point that she even knew the question [about her schooling] would be asked."

After Kathy found out, she said, "I kept thinking to myself, 'Why wouldn't she say something? Why would she not say something?' I also got into such a depression. I didn't want to talk to Paris about it too much until I had talked to a therapist." The mother and daughter continued to do therapy together, much of which Paris chronicled on her reality show.

When the Hiltons moved to New York, Paris Hilton and sister Nicky Hilton were famous for their partying, and the press was all over it. Interestingly, some media outlets brought the family name into their highly-publicized clubbing, claiming that Paris and Nicky were behaving badly because of a lack of parental guidance. Not only that, but some felt that the socialites were tarnishing the Hilton name, too.

"It's disgraceful the way most of them act these days," an insider said to the New York Post in 2000. "If they had any respect for their families they would keep their noses clean." Family reputation aside, Kathy Hilton had a hard time keeping tabs on her daughters, especially Paris. She told Bruce Bozzi on the podcast "Lunch With Bruce" that she got really worried about the growing fame surrounding her daughter. "When I saw all of this happening, it scared me, especially in New York," Kathy said. "I didn't realize what would happen," Kathy said of the endless attention surrounding her daughter.

Kathy had no idea where Paris was at times. "I used to call the city desk at the New York Post," Kathy said. "I would call the city desk and say at one in the morning, 'Excuse me, hi, it's Kathy Hilton. Uh, do you by any chance know Paris, where she is right now?'" Kathy said she had no other recourse to find her daughter at times.

Kathy Hilton graced the screens of the "The Real Housewives of Beverly Hills" in season 11, per ET, to the shock of her daughters, Paris and Nicky Hilton. To clarify, Paris and Nicky didn't know that Kathy was on the series until after she started filming, as the two sisters discussed on Paris' podcast, "This is Paris." "First of all, my mom was so shady about the whole thing," Nicky said. "Pretty much every year this rumors surfaces: 'Kathy Hilton is joining 'The Real Housewives of Beverly Hills.' And we're like, 'No she's not.' This year was no different."

So Nicky spoke directly to Kathy. "I [asked] her, 'Mom, are you going to be on the show?' She's like, 'No,'" she said, adding that it wasn't until later that her mom confessed that she'd been asked to join the cast. Kathy admitted that she was thinking about joining but reassured her daughters that it looked like a long shot. "Cut to Paris and I in Soho walking down the street and our friend FaceTimes us being like, 'I see your mom is on the 'Real Housewives' ... PEOPLE magazine just confirmed it," Nicky said.

For Kathy's part, she told ET that she didn't know why her daughters were so worried. "I know that I'm not going to go and be cursing and starting fights with people," she said. "I don't know if Paris has seen the show, because she's been traveling, but she did send me some memes. They're very much proud," she added.

Kathy Hilton has had a highly publicized feud with sister Kyle Richards. It's publicized because much of their interactions are literally documented on "The Real Housewives of Beverly Hills," along with their sister Kim Richards. Oddly enough, it was Bravo that mended their relationship. "My sister Kyle and I had our ups and downs so it was nothing that I wanted to watch," Kathy told People. "But Kyle convinced me to do it. And I was flattered. I thought it would be an opportunity for us to spend time together. I really missed her."

In July 2021, Kathy got the chance to talk to Bustle about her decision to join her sisters on the reality show. "Kyle and I had issues for a long time, [but] we started getting in a better place," she explained. "It was always maybe, never yes, [then] I finally thought you know what, what do I have to lose?" Kathy knew that she could handle the reality show because of her personality. "I know I'm not a fighter unless I get pushed," Kathy told Bustle, "and I'm not going to cuss or make a ridiculous fool out of myself."

Thankfully, though, Kathy and Kyle have been able to mend their bridges and this gift is not lost on Kathy. "It takes time, but it feels so good to be where we are now," she told People. "And I've really appreciated this time." Sounds like a very happy development.

Money seems to be the ongoing motivation for Kathy Hilton, and by some accounts, she was pretty shrewd (even cutthroat) about how to get it — especially since the Hilton family is famous for withholding much of the inheritance for the heirs. A former friend of Kathy told Vanity Fair that this created a conundrum for Kathy. She had a sterling last name and cultural cache but she didn't have the money to back it up, so this was "why they cultivate friends that have jets and yachts," the friend explained, speaking also of Richard Hilton. "They like to hitch rides," the insider added. If any more proof was needed, when the friend divorced her wealthy husband, Kathy sided with the money, even if she had to befriend the new wife.

The desire for wealth also created some awkward social situations. Jerry Oppenheimer wrote in "House of Hilton" that the entire family was pleased with the intense attention that Paris Hilton was receiving, even if it included her sex tape. "They are proud of everything she has done – even the video."

When Kathy's mother "Big Kathy" died, they hosted a wake at their home and the same friend who spoke to Vanity Fair also recounted, "Paris had just turned 21, and the Hiltons had a running loop of footage from Paris's 21st-birthday party up on their big-screen TV. Rick was running around going, 'Look at Paris!' It was a promotion." Though, from what we know of Big Kathy, she probably wouldn't have minded.

Paris Hilton was engaged to Greek shipping heir Paris Latsis in 2005, according to Vanity Fair. The engagement lasted five months but came with a 24-carat engagement ring that was so valuable that Paris felt the need to get copies made so that she could wear replicas while jet-skiing, for example, in case it falls off.

When they broke up, a different side of Kathy and Richard Hilton came forward. As Jerry Oppenheimer wrote in "House of Hilton," they were hopeful for such an alliance as it would secure the family's fortune. Instead, the wealthy Greek family ignored Paris' parents when thy came to visit them in Greece. To make matters worse, the Latsises felt that Paris wasn't good enough for their son and the rumors were that it was his family who urged him to call off the wedding.

Kathy wasn't one to take this lying down. Later, in the Hamptons, people overheard her saying that Paris Latsis was "lazy and spoiled" and he lacked the gumption that her Paris had to succeed on her own. Sounds like it really wasn't a match. Paris Hilton ended up auctioning off her massive engagement ring, Fashion magazine notes, to support victims of Hurricane Katrina. That seems like a pretty classy move, in our opinion. Maybe the Latsises regret their verdict after all.