There are plenty of people who diss the Kardashian-Jenner family members as “being famous for being famous.” Others have slammed them for their privileged lives. For instance, The Real Housewives of New York City alum Bethenny Frankel took a shot at Kylie Jenner in October 2020 for sharing a “first day of school” photo of her then-two-year-old daughter, Stormi Webster, rocking a backpack worth thousands of dollars. Later that same month, people took issue with Kim Kardashian celebrating her 40th birthday by not only flying people out to a private island amid a pandemic, but also by documenting the trip on social media with a very long caption mentioning the “simple luxury it was to be able to travel and be together with family and friends in a safe environment.”
Yes, this infamous reality TV clan has tons of money, but money doesn’t always buy happiness — a hard truth that the KarJenners know all too well. Given the sheer number of people in this family, it makes mathematical sense that they’ve been through some hard times, often in the public eye. Unfortunately, there are many tragic details that have plagued the Kardashian family for decades.
Robert Kardashian Sr. died eight weeks after his cancer diagnosis
In 2003, The New York Times reported that Robert Kardashian Sr. had passed away. The late entrepreneur, who was perhaps best known as one of the lawyers on O.J. Simpson’s defense team in the ’90s, was 59 when he died — just eight weeks after getting diagnosed with esophageal cancer, according to his ex-wife, Kris Jenner. He was survived by his third wife, Ellen Pierson, and his four kids with Kris: Kourtney, Kim, Khloé, and Rob Kardashian.
Kris later told E! anchor Giuliana Rancic, “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.” Meanwhile, Khloé shared her theory on how the O.J. Simpson trial may have factored into her father’s passing during a 2016 episode of her Kocktails With Khloé talk show. “He never spoke about it,” she began (via In Touch). “My dad also died of throat cancer which does not run in my family. My dad doesn’t smoke, doesn’t drink. I think holding in secrets [and] stress kills you! I feel like you manifest things, you have to think — I’m into symbolic situations.”
As seen above, Kim’s husband, Kanye West, gifted her a hologram of her late father for her birthday in 2020.
The Kardashian family was divided over the O.J. Simpson trial
Anyone who’s watched The People v. O. J. Simpson: American Crime Story knows that former couple Robert Kardashian Sr. and Kris Jenner fell on opposite sides when O.J. Simpson was on trial for the deaths of Ron Goldman and Nicole Brown Simpson. On David Letterman’s My Guest Needs No Introduction, Kim Kardashian revealed that her mom, who had been close friends with Nicole, “was extremely vocal on her feelings.” Meanwhile, Kim’s late father was on O.J.’s defense team.
Kris “believed that her friend was murdered” by the former athlete-actor, with Kim calling the experience “really traumatizing” for her momager. “We’d go to my dad’s house and it was a whole other situation there,” Kim continued. “And it would be like Johnnie Cochran, Bob Shapiro, my dad, like the whole team.” As a result, Kim and her siblings “really didn’t know what to believe or whose side to take.”
“It kind of tore our family apart, I’d say, for the whole time of the trial,” Kim admitted. Indeed, in a 1994 interview with Inside Edition, Kris said, “Not only have we lost Nicole, we’ve lost O.J., too.”
Kim Kardashian was robbed at gunpoint in Paris
In October 2016, Kanye West stopped performing in the middle of a concert, telling the crowd (via People), “I’m sorry. Family emergency, I have to stop the show.” What he’d learned was that wife Kim Kardashian had been robbed, tied up, and held at gunpoint in her Parisian hotel room. The following January, ET translated the police report from Le Journal du Dimanche, a French newspaper, which stated that Kim had told the authorities, “I was wearing a bathrobe, naked underneath. They pushed me on the bed and strapped me with plastic cables, taping my hands, mouth and legs. They carried me into the bathroom, more specifically, the bathtub.”
At the time, Kim estimated that $5 million worth of jewelry was stolen. During her 2020 interview on David Letterman’s My Next Guest Needs No Introduction, Kim publicly shared more details about the incident. Fearing that she was “going to get raped” after being tied up, she’d told herself to “just deal.” When the man pulled out a gun, Kim thought of her sister, Kourtney Kardashian, telling herself, “She’s gonna come home, and I’m gonna to be dead in the room. She’s gonna be traumatized for the rest of her life if she sees me.”
Thankfully, Kim survived the ordeal, and the perpetrators were eventually arrested (via ET). Even so, she’s understandably struggled with anxiety after the incident.
Kris Jenner regretted cheating on Robert Kardashian
Kris Jenner has publicly discussed cheating on her first husband, Robert Kardashian Sr., with a soccer player named Todd Waterman a few times, often noting the negative impact the affair had on their family. “I had a wonderful, beautiful life with Robert,” she told Harper’s Bazaar in 2016. “He was just an amazing man.” While appearing on Diane von Fürstenberg’s podcast, InCharge with DVF, in 2020, Kris revealed, “I had an affair and my biggest regret was the fact that it broke up my family.”
Indeed, when Kris released her book, Kris Jenner … And All Things Kardashian, she further dished on the affair, which upset daughter Kourtney Kardashian during a 2012 Keeping Up With the Kardashians episode. Per the Daily Mail, Kourtney told her mom, “I don’t understand how you can do that to your family.” At another point, Kris asked Kourtney, “Are you going to punish me for the rest of my life because of something I did 25 years ago?”
Meanwhile, Khloé Kardashian explained on Kocktails With Khloé that this experience is exactly why she could never cheat on a partner, recalling (via People), “I saw how it destroyed my dad … I also saw the regret from my mom.”
Caitlyn Jenner trashed ex Kris Jenner in her book
In 2017, former Olympian Caitlyn Jenner angered the Kardashians due to claims made about ex-wife Kris Jenner in her book, The Secrets of My Life – namely, alleging that Kris knew more about her true gender identity than she had publicly let on when Caitlyn transitioned.
“[Kris] insists that she was taken by surprise by my ultimate transition to Caitlyn, which obviously means in her mind that she did not know enough,” Caitlyn wrote. “On Keeping Up With The Kardashians she shed copious tears in coming to grips with it. Given what she saw, the whole reaction seemed a little puzzling then and seems puzzling now.” Noting that their marriage “became acrimonious misery” in her book, Caitlyn also admitted to intentionally excluding the Kardashian side of the family from her Diane Sawyer interview, in which she came out as a transgender woman, “because of research showing that anytime a Kardashian is on television, many in the public tend to think it is a publicity stunt to make money.”
Speaking about the book in a KUWTK episode, Kris claimed, “Everything she says is all made up.” Meanwhile, Kim Kardashian remarked, “Caitlyn has every right to feel however she feels, but why bring my mom into it one more time? I just feel so bad for my mom.”
Lamar Odom admitted to cheating on Khloe Kardashian
It’s not exactly a secret that Khloé Kardashian’s marriage with former NBA star Lamar Odom was full of drama. To recap: Lamar rapped about cheating on her in 2013, saying, “Khloé’s out of town. I guess I still be on the DL,” and during an episode of Keeping Up With the Kardashians, Khloé later admitted she’d “lied to everyone” about spending her birthday with her husband when she was actually alone while he was with another woman, per the Daily Mail. At the time, Khloé confessed, “Everything I did I had to hide or conceal or cover up.”
Lamar later told Us Weekly that he’d also been “hiding” his drug use from Khloé during this time, but she eventually found out. Noting that Khloé didn’t “accept” his behavior, but “tolerated” his antics, the former Laker player said, “If there is one thing I regret when I was married, it was having multiple affairs with different women.”
But even after Khloé and Lamar split in December 2013, their relationship was tumultuous. Two years later, Lamar suffered 12 strokes, six heart attacks, and slipped into a coma at a Las Vegas-area brothel. Khloé initially called off the divorce, with Lamar telling Us Weekly that she “played a major role” in helping him recover and get his memory back after the incident. By October 2016, the on-and-off couple were officially divorced.
Tristan Thompson cheated on Khloe Kardashian while she was pregnant
When Khloé Kardashian announced that she and NBA star Tristan Thompson were expecting a child together, it seemed as though she’d finally found her happily ever after. But it all appeared to come crashing down in April 2018, when TMZ shared footage of Tristan heading into a hotel with another woman, while Khloé was preparing to give birth to their daughter, True. Despite more cheating allegations coming out that same day, Tristan was in the delivery room with Khloé just hours later, along with the rest of her family, who understandably had tension with Tristan, per People.
The new parents managed to quietly stay together throughout the scandal, but Tristan reportedly slipped up again less than a year later, this time with Kylie Jenner’s then-BFF, Jordyn Woods. Jordyn later claimed it was just a peck on the lips when she appeared on Red Table Talk. Regardless, Khloé and Tristan split up after the incident came to light in February 2019.
However, by August 2020, Us Weekly reported that they’d gotten back together, citing a source that claimed the reality starlet was “hopeful” about their future. That October, E! shared clips of the on-and-off couple getting cozy at Kim Kardashian’s birthday celebration. They basically confirmed their reconciliation with coordinating Halloween costumes later that month.
Caitlyn Jenner wasn't there for her own kids
Caitlyn Jenner shares six children with three women: Burt Jenner and Cassandra Marino with Chrystie Crownover, Brody and Brandon Jenner with Linda Thompson, and, of course, Kendall and Kylie Jenner with Kris Jenner. However, in more recent years, the former Olympian has admitted to some regrets about her parenting history, especially with her four eldest.
“I was too busy struggling with my own issues and my own self. I very much regret … that I wasn’t there more for my young kids,” she said on the Literally! With Rob Lowe podcast, further noting on Woman’s Hour, “I can’t use that as an excuse … no matter what your problems are, you gotta be there for your kids. And I really wasn’t.”
Concurring with Caitlyn’s confession, Brandon claimed in To Me, He Was Just Dad, “I didn’t see my father more than half a dozen times between ages eight and twenty-five.” Similarly, on The Hills reboot, Brody revealed (via Us Weekly), “Bruce was just never really around … So, yeah, it really wasn’t any relationship.” For her part, Cassandra told People, “My relationship with Caitlyn is much better than with Bruce, but we still have a lot of work to do. We didn’t talk for years, and now we see each other every couple of weeks and talk on the phone.” Meanwhile, Burt told Vanity Fair, “I have high hopes that Caitlyn is a better person than Bruce.”
Both of Scott Disick's parents died within months
Scott Disick, who shares three children with ex-girlfriend Kourtney Kardashian, sadly lost both of his parents in the span of a few short months. After his mother, Bonnie Disick, died following an undisclosed illness (via Us Weekly) in November 2013, E! confirmed the following January that his dad, Jeffrey Disick, had also passed away. His cause of death was never officially revealed, but Scott previously mentioned that his father had suffered “from diabetes and need[ed] a heart replacement” during a Keeping Up With the Kardashians episode, per Hollywood Life.
Although viewers saw Scott struggling with the aftermath of the losses, he didn’t open up about it until a 2020 episode, where he explained, “You know, I don’t think I was really ready to talk about my family. But now, I think the more I talk about my parents, the more my kids will feel connected to them and remember them.”
That May, Scott’s attorney confirmed to E! that the reality star went to a rehab center “in an effort to finally come to terms and deal with the pain that [he] has been silently suffering for many years due to” his parents’ sudden deaths. Unfortunately, Scott’s privacy was violated when someone leaked a photo of him at a group meeting. As a result, he checked out of the facility.
Was Scott Disick caught with another woman while dating Kourtney Kardashian?
In 2015, the Daily Mail shared photos of Scott Disick in Monte Carlo with Chloe Bartoli, his ex-girlfriend. While he reportedly “put his arm around” her, she allegedly “fed him food off her plate.” Meanwhile, a source cited by Us Weekly claimed, “Scott and Chloe flirt all the time. Kourtney [Kardashian] does not want her around Scott.”
While a source close to Chloe told E! that “nothing happened between her and Scott,” the damage was done. Soon after the photos leaked, an insider shared with the outlet, “Kourtney dumped him after she saw the pics [in Monte Carlo] and he hasn’t been home after a month-long party binge.” Keeping Up With the Kardashians documented the aftermath that September, which included Kourtney crying as she said, “I worked so hard to keep this family together.”
This was understandably a difficult and public ordeal for the entire family (and everyone who ships Kourtney and Scott as a couple). Nevertheless, in time, Kourtney and Scott became amicable co-parents to their kids.
Caitlyn Jenner was involved in fatal car crash
In February 2015, two months prior to Caitlyn Jenner’s transition, the reality TV alum was involved in a fatal multi-car crash. According to CNN, the former Olympian’s car rear-ended a Lexus driven by a woman named Kimberly Howe. The collision sent her vehicle into oncoming traffic, which was then “struck head-on by another vehicle, killing her.” The I Am Cait alum wasn’t injured, but five children and two adults were hospitalized following the incident.
“My heartfelt and deepest sympathies go out to the family and loved ones, and to all of those who were involved or injured in this terrible accident,” Caitlyn stated at the time (via E! News). “It is a devastating tragedy and I cannot pretend to imagine what this family is going through at this time. I am praying for them. I will continue to cooperate in every way possible.”
R Online reports that Caitlyn didn’t appear to be on the phone, but was reportedly smoking a cigarette moments before the accident. The father of six, who had engaged her brakes prior to impact, told the court that paparazzi played a role in the accident, according to USA Today. Prosecutors didn’t charge the star with any crimes, but ABC News reports that Caitlyn would pay $800,000 to settle a wrongful death civil lawsuit stemming from the crash in 2018.
Kim Kardashian almost bled to death while giving birth
Kim Kardashian shares four kids with husband Kanye West, but it certainly wasn’t easy for her to become a mom. In 2019, the TV personality opened up about her fertility struggles, which included a miscarriage scare during her first pregnancy due to heavy bleeding, on Instagram. “When I was pregnant with my daughter North, I had a condition called preeclampsia or toxemia, which is basically when the mom’s organs start to shut down,” she shared, revealing that “the only way to get rid of that is to deliver the baby.”
Kim was induced into “emergency labor,” but that wasn’t the end of her troubles: “After I delivered, my placenta never came out, so that’s called placenta accreta. So, my placenta grew inside my uterus.” Kim previously told Elle this condition is “what women usually die from in childbirth,” explaining, “You hemorrhage and bleed to death and they can’t stop it.”
Unfortunately, Kim suffered from the same conditions during her second pregnancy with son Saint, too. Following these complicated pregnancies, she and West welcomed daughter Chicago and son Psalm via gestational carrier.
Kanye West bashed the KarJenners amid his mental health struggles
Kanye West has long been open about his diagnosis with bipolar disorder, and once referred to his mental illness as his “superpower” when tapping into his creativity, per Forbes. However, a series of events in the summer of 2020 caused growing concern for his well-being among the KarJenner clan.
After announcing his ill-fated run for president, Kanye shared a series of now-deleted tweets about the family, particularly wife Kim Kardashian and mother-in-law Kris Jenner. “Kim was trying to fly to Wyoming with a doctor to lock me up like on the movie Get Out because I cried about saving my daughters life yesterday,” referring to his revelation that he initially wanted Kim to get an abortion when she was pregnant with daughter North West, per People. He made a similar claim against Kris, whom he’d nicknamed “Kris Jong-Un,” writing that she was “not allowed around [his] children,” the outlet reports, also writing in another tweet that he’d been “trying to get divorced” from Kim since November 2018.
Addressing her rapper husband’s alarming social media activity, Kim released a statement. “As many of you know, Kanye has bipolar disorder. Anyone who has this or has a loved one in their life who does, knows how incredibly complicated and painful it is to understand,” she said in part (via TMZ). Seemingly, Kanye, Kim, and the family have worked through those struggles privately.
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