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15 Times The Hilton Family Was Crazy AF

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15 Times The Hilton Family Was Crazy AF

The Hilton family is known around the world for having the world’s first international hotel chain. What we all also know is just how scandalous this high profile family really is. Between affairs, a sex tape, drugs and plenty of parties, this family has had their share of crazy af moments.

If a man named Augustus Halvorsen Hilton hadn’t come to America from Norway, we might not have had the Hilton Hotel chain and the massive empire that went with it. It wasn’t Augustus’ fate to go out with the intentions of buying a bank, coming back, instead with a hotel; it was his son’s, Conrad Hilton. After a series of endeavors, Conrad Hilton Sr. formed the Hilton Hotels Corporation in 1946, and just two years later, he founded the Hilton International Company, the world’s first international hotel chain. He made a killing renting hotel rooms out to workers in eight hours shifts. By using his quick turnover method, he could have up to three bookings a room each day!

Although Conrad Hilton Sr. remained prosperous for the remainder of his life, he didn’t want to simply hand over his vast wealth to his surviving family. He wanted them to work hard for it as he had. In his will, he had asked that most of his money be given to a charity. Of course, deeming this act unfit, his son, Barron began a ten-year-long battle in court to get the will overturned.

These secrets, along with dozens more, haunt the Hilton family on a daily basis and one family member’s crazy antics usually causes strife for the rest of the family. You might just think that Paris is the most scandalous of the clan, but you’ll be surprised to learn that there are people in the Hilton family with even more skeletons in their closets than Paris.

15. There Was Almost No Fortune

Just imagine the Hilton family if the entire Hilton fortune had just been handed over to charity. Conrad Hilton Sr. has written these steep terms in his will, as his dying wish. He didn’t feel like his family deserved the money he had worked so hard all his life for. Believing that this was an unjust act, one of Conrad’s sons, Barron, challenged the will and wished to have it overturned. He went to court and fought for ten long years before he got what he wanted. The will was overturned and the Hilton family fortune, well most of it, remained within the family. Could you just imagine a time where the Hiltons weren’t filthy rich? In an ironic turn of events, Barron also tried to donate the majority of the family fortune to charity after some of Paris’ crazy antics really ticked him off.

14. When Paris Made A Tape

Now, this is something that just about everyone knows about. It was the biggest celebrity news in 2004 and it has still been referenced every year since. So what happened? Well, in 2001, Paris had sex with her then-boyfriend, Rick Salomon. Although she was well aware that he was recording their time together, she says that the video was never intended for public release. In fact, she sued him not just for defamation of character but for releasing the tape in the first place; she won $400,000 for his actions. As for the movie in question, Paris has surprisingly never seen a dime from the film, which has since been sold to Vivid Entertainment. Some people assume that because the sex tape was released right before the first airing of Paris’ TV show, The Simple Life, the whole thing was set up just for publicity. Paris certainly isn’t proud of this moment, but it has won her several AVN awards both in 2005 and 2008.

13. Mary Hilton Had An Affair With A Football Coach

Conrad Hilton Sr. had a very busy life, but his love for hard work, success, and more money eventually lost him the love of his first wife, Mary Adelaide Barron. Mary and Conrad got married in 1925 and together they had three children, all boys. Because of her husband’s work, Mary often felt lonely and sought out something to pass the time. She found a man, a football coach, that she had strong feelings for, and the two started an affair. In 1934, Mary decided to disengage herself from the Hilton family and she left Conrad for her new man. Although it left him crushed, he soon found solace in a Hungarian beauty queen.

12. Conrad’s Love Of Drugs

Conrad Hilton III has been battling with drug addiction since he was a teenager, a problem that has only increased since he’s gotten older. Some of the more extreme events surrounding Conrad Jr.’s drug problem includes several violent, aggressive, and downright horrific outbursts, not only while on a flight back in 2014, but also while engaging with police in May 2017 after he was caught breaking into his ex’s house, again. Another event was when he was sentenced to prison for two months after violating the terms of his parole because he failed to pass a drug test on more than one occasion. Regardless of what his family tries to do for him, he just keeps getting more and more out of control.

11. Zsa Zsa Was Given A Shocking Surprise

When Zsa Zsa Gabor was spotted by Conrad, he knew he had to have her. Zsa Zsa had a previous reputation for being a gold digger and she knew that if she could hook a man like Hilton, she could have anything she could ever dream of. Knowing her story, and not wanting to be taken advantage of, Conrad Sr. gave Zsa Zsa a choice of a ring with a modest stone or one with a stone the size of a massive rock. Knowing that by seeming humble, she would ultimately win the bigger catch, Zsa Zsa chose the smaller of the two rings and the beauty queen and the hotel tycoon were wed. Zsa Zsa thought she had life in the bag, but instead, she was in for a nasty shock. Instead of getting everything she had ever wanted, she got a boring room down the hallway, a very measly allowance, and strict rules for just about everything. Not exactly what she had expected from a man made of millions.

10. Nicky Hilton Stole His Dad’s Wife

When Conrad Sr. had brought beautiful Zsa Zsa Gabor into his life, his eldest son, Nicky quickly took notice. He thought that she was absolutely stunning and he couldn’t keep his eyes off of her. He didn’t care that she had just married his father. In fact, after seeing his father kiss his new bride, Nicky had asked how he could manage to get her to kiss him like that. He eventually got a chance to find out since he and his father’s wife started having an affair before she and Conrad Sr. divorced after only being married for two years. Zsa Zsa has said that the affair between her and Nicky started before she had divorced his father and didn’t end until well after his betrothal to Elizabeth Taylor.

9. When Paris Dropped Drugs In Front Of A Cop

In 2010, Paris and her then-boyfriend, Cy Waits were driving around Las Vegas in a black Escalade. Unfortunately for them, their vehicle reeked of marijuana and they were pulled over by local law enforcement. Now, if Paris had just kept still during this situation, she would have just been dealing with the issue of the weed. Instead, she reached out to grab her chapstick from her purse inside the car when a tiny bag of cocaine fell out of her bag right front of the cop. Needless to say, she and Cy were charged for possession. Even though she was caught red handed, she didn’t seem all that concerned with the ordeal in her mugshot.

8. Conrad Sort Of Denied Being Francesca’s Father

Technically, he shouted at her that he didn’t even know if he was the father or not, and honestly, he had all the reason to wonder. Constance Francesca Hilton is the only child of Conrad Hilton Sr. and Zsa Zsa Gabor. In her autobiography, One Lifetime Is Not Enough, Gabor says that Conrad had raped her during their marriage and the result of the confrontation was Francesca. Since Zsa Zsa was known to bed other men than just her husband, Conrad had doubt that Francesca was even his. He made sure his “supposed” child was aware of his feelings when he left her only a scrap of the fortune he had inherited.

7. Nicky Hilton Caused Elizabeth Taylor To Miscarry

Nicky was the eldest son of Conrad Sr. and he was also the most troubled. After having an affair with his step-mother, Nicky Hilton went on to become the first husband of Elizabeth Taylor in the most lavish wedding of 1950. However, it was not life in paradise for the two young lovers. Due to the partying and drug induced lifestyle he was leading, he would often get abusive towards Taylor, who, in turn, dished it right back. The fighting within the relationship got so bad that one day, while Elizabeth was pregnant with their child, Nicky threw a fit a kicked his wife straight in the stomach and she miscarried.

6. The Time Nicky Hilton Got Married At The Las Vegas Chapel

In 2004, Nicky, as in Paris Hilton’s sister, made a split decision and married Todd Meister in the wee hours of the morning at the Las Vegas Wedding Chapel. Although Nicky’s spokesperson, Elliot Mintz, claims that the two had long been planning a wedding that was destined for that fall anyways, and they thought that by doing something spur of the moment, like in Vegas, they would be able to make it a more intimate affair. So, at 2:30 in the morning on August 15th, Nicky Hilton and Todd Meister said: “I do.” Unfortunately, due to working in two separate cities, along with the fact that they married in Vegas on a whim, the two both amicably called it quits and had the marriage annulled. It didn’t even last three months.

5. Barron Cost His Parents $4.6 Mil For A Fine

Back in 2008, Barron was charged with a DUI for hitting a gas station attendant with his car. The man, Fernando Telez, was seriously injured and took action against the young Hilton. He said that since his back had been broken in the accident, he hadn’t been able to find any work, a situation that awarded him a good amount in damages. In addition to Hilton’s insurance company having to pay up $4.6 million for fines associated with the drunk driving incident, he had to cough up another $225,000 in punitive damages. This kid not only ruined someone’s life, but he cost his parents a boatload of money. We wonder what his insurance rates looked like after that costly mistake.

4. Lindsay Lohan Had Paris’ Little Bro Beaten Up

2013 saw an interesting event unfold when a member of Lindsay Lohan’s entourage beat up Paris’ little brother, Barron. In December of that year, Lindsay and some of her friends, one of which was the assailant, Ray LeMoine, rented a mansion in Miami for a few days. Apparently, Lindsay had overheard the young Hilton talking trash about her to some of his friends, upon hearing this, she ran upstairs and supposedly ordered Ray to go beat him up. LeMoine claims that he only got physical AFTER he had asked Barron to leave the mansion. Barron was taken to a nearby hospital in Miami and treated for his injuries while Ray LeMoine was arrested for assault. After the confrontation, Barron told police that Lindsay had gotten in his face screaming “You talk s*** about me to my boyfriend, this is what you get.”

3. When Drugs Were Found On Their Property

It may have never been pinned on them, but in 2014, 400 kilos worth of cocaine was seized from a small airplane that had been using a Hilton airstrip to traffic drugs in Costa Rica. Along with the drugs, $1.5 million in cash was found at the Rancho Horizonte farm in Canas. One prosecutor in the case said that the farm was connected to several United States shareholders and that supposedly, the Hilton name was included in the title. However, the Hilton family played dumb and the authorities left them alone. Since certain members of the Hilton family, we’re looking at you Conrad and Paris, have had huge problems with drugs, especially cocaine, in the past, the accusation that the Hilton is wrapped up into this isn’t all that far-fetched.

2. Paris Hilton Became A DJ

It may come as a surprise, especially after hearing of her crazy antics throughout the years, but Paris Hilton has successfully gone from Party Queen to International DJ. Her debut at the Sao Paulo Pop Music Festival in 2012 didn’t go as she had hoped, in fact, the fans at the festival booed her when she came out on stage. Despite the initial crowd opinion, Paris was determined to make a name for herself within the music industry. In 2013, she did a great job at establishing her name by getting a residency in Ibiza and being backed by Birdman himself. Although she denied being a DJ in 2014, claiming that she was simply a business woman, she has taken her career as a DJ to new heights with each passing year.

1. Conrad Won’t Leave His Ex Alone

Conrad Hilton III dated a girl named Hunter Salomon, yes, the daughter of Paris’ sex tape partner Rick Salomon, and it was the worst mistake of this young girl’s life. Even though she dated him years ago, Conrad hasn’t let a day go by without expressing his obsessive feelings of love. In 2015, she filed a restraining order against him that he soon violated when he tried to break into her parent’s house where she lived. More recently, as in May of 2017, Conrad III was caught once again violating the terms of the restraining order and once again breaking into Hunter’s parent’s house. This time he took things to the extreme when he also stole her dad’s car and went out for a joyride. If the girl takes out a restraining order against you, you need to let her go man.

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