Kris Jenner Opened Up About Robert Kardashian – And Revealed Her Biggest Regret Of Their Marriage

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Kris Jenner divorced Robert Kardashian back in 1991. Since then, her life has changed beyond recognition, following her family’s journey into the spotlight. And she’s at the helm of all their success. But while the momager might appear to have it all, she’s still haunted by something that happened during her first marriage.

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Kardashian and Jenner first met at California’s Del Mar racetrack in the spring of 1973. Back then, he was reportedly among Hollywood’s most eligible bachelors. She, though, was just 17 years old at the time and dating professional golfer Cesar Sanudo, a man over ten years older than her. His job, however, meant that he was away much of the time.

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Despite the teen’s relationship with Sanudo, Kardashian was reportedly smitten with the girl he thought resembled actor Natalie Wood. And it appears Jenner couldn’t resist the smooth-talking lawyer’s charms. Because one night, when her boyfriend was out of town, she invited him over to the golfer’s house.

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But Jenner had no idea Sanudo planned to surprise her that night. As a result, the golf pro arrived home, only to find his girlfriend shacked up with another man – in his house. As you might imagine, he was not impressed. In a 2018 episode of Keeping Up With The Kardashians Jenner revealed, “It wasn’t pretty, I’m not proud of it.”

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It’s safe to say, then, that the couple’s relationship got off to a dramatic start. But it appears that life wasn’t about to get any smoother for either one. That’s because, according to Jerry Oppenheimer’s book, The Kardashians: An American Drama, the lawyer later dumped Jenner for Priscilla Presley.

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While romance bloomed between Kardashian and Presley, Jenner was thousands of miles away. She was actually in New York, where she worked for American Airlines as a flight attendant. However, she reportedly pined over her ex, telling friends all about him and admitting that she still hoped to marry the lawyer one day.

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Luckily, things took a turn in Jenner’s favor when Kardashian and Presley called time on their relationship after only 12 months. The latter reportedly vowed that she wouldn’t marry again until her ex-husband, Elvis, died. With that in mind, her relationship with the lawyer simply ran its course.

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Following Kardashian’s split from Presley, he soon rekindled his romance with Jenner. This time around, though, he was allegedly eager to make the flight attendant his wife and quickly proposed to his girlfriend. However, the future momager wasn’t ready for that type of commitment and reportedly turned him down flat.

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But it appears that Kardashian was incredibly persistent in his mission to make Jenner his wife. And when he asked her to marry him for a second time she finally said yes. The couple tied the knot in 1978 and the following year they welcomed their first child together – a daughter named Kourtney.

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Altogether, the Kardashian’s marriage would produce four children. They welcomed their second daughter, Kim, in 1980. Khloé followed in 1984, while their youngest child and only son, Rob, was born in 1987. The couple raised their kids in an exclusive part of Beverly Hills complete with tennis court, swimming pool and Jacuzzi.

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The couple were known for throwing lavish parties at their luxurious home and often rubbed shoulders with Hollywood’s elite. The Kardashians counted stars including Lionel Richie and Sugar Ray Leonard as friends. However, they were particularly close to O.J. Simpson and his wife, Nicole Brown Simpson.

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Kardashian and O.J. met in their college days in the late 1960s while attending the University of Southern California. They then resumed their friendship sometime later, when they reunited over tennis at the home of a mutual acquaintance. After that, the pair grew extremely close, even going into business together.

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When Kardashian and Jenner married in 1978, O.J. served as his best man. Meanwhile, after the NFL star tied the knot with Nicole in 1985, the two couples were known to hang out frequently. The families even vacationed together, and the Kardashian kids knew the Simpsons as “Uncle O.J.” and “Auntie Nicole.”

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However, the good times were not to last. In 1991 the Kardashians divorced. The split would have a huge impact on their family, particularly affecting their two oldest daughters, Kourtney and Kim, who were around 12 and 11 years of age at the time. The Simpsons followed suit a year later, splitting in 1992.

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In 2014, during an appearance on The Talk, Jenner opened up about her divorce from Kardashian and the effect it had on their family. She said, “It was not fun. It was so scary. I was so young, and I had four kids… There was a period of a couple of years in there where it was really ugly and hard, and you didn’t want the kids to take sides.”

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And the Kardashian family was put under further strain in 1994 when O.J. was put on trial for the murder of his ex-wife Nicole. Found dead at her Los Angeles home on June 12, 1994, she’d suffered multiple stab wounds. Her friend Ron Goldman, a 25-year-old waiter, also lost his life in the frenzied attack.

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Kardashian decided to join his friend’s defense team at his trial, despite not having served as a lawyer for 15 years. But while he believed Simpson innocent of the murders, Jenner often appeared in court alongside Nicole’s family. Furthermore, in her memoir Kris Jenner… And All Things Kardashian, the momager revealed that she “never believed O.J., not for one second.”

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O.J. was acquitted of killing Nicole and Goldman at his criminal trial in 1995. However, in 1997 he was found liable for their murders in a civil judgment. For Kardashian’s part, he later admitted to questioning his friend’s innocence. In a 1996 interview with Barbara Walters, he said, “I have doubts. The blood evidence is the biggest thorn in my side; that causes me the greatest problems. So I struggle with the blood evidence.”

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With the drama of O.J.’s trials behind them, Kardashian and Jenner were later able to reconcile. The momager told The Talk, “We ended up being best friends.” In fact, the lawyer remained an important part of her family even after she’d found love again. She married Olympian Bruce Jenner – who became known as Caitlyn Jenner in 2015 – just four weeks after her divorce came through.

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With Caitlyn, Jenner had two more children – welcoming daughter Kendall in 1995 and her sister Kylie two years later, in 1997. In a touching tribute, the momager gave their oldest child the middle name Nicole, in honor of her fallen friend. The couple eventually separated in 2013, before divorcing in 2015.

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Meanwhile, following Kardashian’s divorce from Jenner, he was engaged, for a time, to Denice Shakarian Halicki. He later married Jan Ashley in 1998, but the couple annulled their vows after just 30 days. In the three years prior to his death, the lawyer dated Ellen Pierson. They married in 2003, just six weeks before he died.

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Kardashian learned he had esophageal cancer in July 2003 and passed away just two months later, on September 30. He was 59 at the time of his death. Jenner, reflecting on the loss of her first husband on a 2014 episode of Beyond Candid With Giuliana!, said, “It was so surreal. The knowledge he had cancer was one thing, but to think it would actually take his life, I never in a million years thought that would happen to him.”

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In the years after Kardashian’s death, Jenner and their family found themselves propelled into the spotlight. That’s thanks, in part, to the success of their E! reality TV show, Keeping Up With The Kardashians, which launched in 2007. However, the family has also made millions through their many product lines, endorsements and fashion collaborations.

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Kardashian didn’t live to see his family become world-famous. But his children and ex-wife strive to keep his memory alive and mention him often. Kim and her siblings frequently take to social media to mark special occasions, including the anniversary of their father’s passing and his birthday. And even Jenner herself also talks fondly of her first husband.

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In fact, Jenner spoke about her relationship with Kardashian at length in her 2011 memoir Kris Jenner… And All Things Kardashian. Within its pages, she revealed her number one regret about their marriage. And in doing so,  the momager made a candid admission about her own behavior during their union.

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That’s because the Kardashians’ marriage ended after Jenner cheated on her husband with soccer player Todd Waterman. In her autobiography, she described the romance as, “Wild crazy sex all the time.” She went on, “We had sex in cars, sex on the tennis court, sex in the pool house, sex in the garage when we got home, sex up and down the stairs, sex everywhere, all the time.”

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In the memoir, Jenner claimed that Kardashian eventually caught wind of her affair with Waterman. As a result, he hired private investigators to catch the pair in the act. He eventually found them together at a Beverly Hills restaurant and subsequently filed for divorce. In doing so, the lawyer also cut off his wife’s credit cards, forcing her to fend for herself financially.

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Jenner also opened up about her divorce from Kardashian in March 2020. The momager made an appearance on InCharge With DVF, Diane Von Furstenberg’s podcast. And during her conversation with the famous fashion designer, she described her fling with Waterman as her “biggest regret.”

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Speaking on the podcast, Jenner revealed, “I got married when I was very, very young. I met [Kardashian] when I was 18 years old. We dated for four years, got married at 22, sooner or later during my life, when I was in my 30s, I had an affair. And my biggest regret was the fact that it broke up my family.”

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It’s not the first time that Jenner expressed regret over her affair with Waterman. In a 2018 appearance on the OBJECTified podcast, she said she enjoyed the “happiest life you could’ve dreamed about” with Kardashian. Regardless, she was restless. The momager explained, “When you’re in something, sometimes people think the grass is always greener. And that was like what I think I went through at some point.”

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Jenner’s divorce from Kardashian forced her into financial independence. And at first, the lone parent struggled to adjust after living a life of luxury during her years of marriage. On InCharge With DVF, she explained, “I didn’t know what to do. I had four kids, I was single. I didn’t know where I was going to live.”

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Jenner continued, “I didn’t know what I was going to do. I didn’t know how I was going to make a living. It was the scariest time to be that young. I think I was 32 years old, and I had four children. My son was maybe a year old and it was scary. I was really, really scared. I remember picking myself up by my bootstraps one day.”

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However, Jenner claimed that it was her religion that eventually gave her the strength to step up and take responsibillity. She revealed, “I have deep faith in God. I just started praying that God would just strengthen me, give me that power, give me the ability to be in charge of my own life. It was my turn to really grow up.”

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Jenner reportedly tried out “several different jobs,” in a bid to support herself and her family. And while she was in the midst of figuring things out, she met Caitlyn. That meeting ended up changing the course of her life once more. Because not only did she marry the Olympian, but their union also gave her a taste for being a manager.

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During Jenner’s interview with InCharge With DVF, she revealed how she found her niche. It appears that the future momager played an integral part in helping Caitlyn establish a motivational speaking career. She said, “We started dating and that happened really quickly and all that I noticed – and I’m sure he would agree with me – was that he wasn’t really taking advantage of all the gifts that he had.”

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That’s where Jenner stepped in. She explained, “He wanted to be on the speaking tour and do all these different things. And I don’t know really where it all came from, but by trial and error and by really rolling up my sleeves and trying to figure it out, I was able to get his speaking career started again.”

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So it was through Jenner’s work with her second husband that she discovered her managerial talents. She would later use these skills to make her own family famous. It was, in fact, the momager who saw the entertainment value in the blended Kardashian-Jenner clan. Then, in 2007, she decided to pitch the idea for a family reality TV show to Ryan Seacrest.

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In 2015 Jenner told the New York Times Magazine that she felt like her family were perfect for such a format. She said, “Like, there’s the little girls, and there are the older girls, and then there’s my son… Everybody thinks that they could create a bunch of drama in their lives, but it’s something that I felt I didn’t even have to think about. It would be natural.”

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So while Jenner may always regret her divorce from Kardashian, it helped make her the woman she is today. Indeed, if she hadn’t had to provide for herself she may never have become the momager of what could be the world’s most famous family. Today she is at the head of a successful business empire, with a reported net worth of $37.5 million, as of 2018.

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And following Jenner’s split from Caitlyn, it appears that she’s found love once more. Since 2014 she’s been dating road manager Corey Gamble, a close friend of Justin Bieber. However, the momager recently claimed that she won’t wed again due to the experiences of her two previous marriages.

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