CHAPTER FOURTEEN 

When Bob Kardashian died in 2003 from esophageal cancer, his only son, sixteen at the time, was living with him and Bob’s new wife, Ellen. His father’s death hit him hard, which is perhaps why he would establish such a strong bond with his sister Khloé, who was also profoundly affected by Robert’s passing.

According to Kris, Robert’s dream had been for his son to attend his alma mater, the University of Southern California. Bruce had reportedly promised Robert on his deathbed that he would take care of his children. To keep that promise, he embarked with Kris on what they called the “Get Rob into USC” campaign. Rob’s high school marks were not stellar and did not guarantee acceptance. But when Bruce met personally with the dean of admissions, a letter of acceptance soon followed, and Rob was admitted into the school’s Marshall School of Business.

Rob wouldn’t graduate from USC until 2009, a full two years after his family exploded to stratospheric success and his sisters struck gold in their various enterprises. On his Keeping Up with the Kardashians appearances, Rob never really made much of an impression during the early years, except in episodes where his sisters got involved in his flailing love life while he was dating the actor and singer Adrienne Bailon, whom he ended up cheating on. A recurrent theme in those years was Rob’s desire to launch a menswear line or open up a men’s version of his sisters’ D-A-S-H boutiques. After graduating from USC, he had started his own skin-care company, Perfect Skin, but it never really seemed to go anywhere. Eventually he settled on the idea of launching a line of high-end socks, but for a long time it never got off the ground because, as we see him repeatedly stew, nobody is interested in helping him out. It’s all about his sisters.

The high point perhaps of Rob’s career came in 2011, when he appeared on season 7 of the hugely popular TV show Dancing with the Stars, on which his sister Kim had flamed out in spectacular fashion three years earlier. Unlike her, he displayed a surprising grace, paired with Cheryl Burke, and ended up in the finals, coming in in second place against the eventual winners, J. R. Martinez and Karina Smirnoff. He also did some modeling for the agency Nous Model Management.

In 2011, Khloé and her husband, Lamar, were given their own spinoff and, as it turns out, Khloé and Lamar finally offered Rob his turn in the spotlight. He ended up moving in with his sister and brother-in-law during the first season, and we quickly discover that Rob and Lamar have bonded in a significant way.

“Having Lamar as a brother now, it definitely makes me realize how much I miss not growing up with a brother,” Rob says in an early confessional. The bromance plays a significant part during the spinoff’s first season, and it is soon evident that the bond with Lamar is an important emotional anchor for Rob.

By season 2, Rob has moved out but he still ends up featured prominently, as we discover that he has obsessive-compulsive disorder and that Khloé is very concerned about it. “I really am worried about Rob,” she says. “I definitely think he has a bigger problem than what he’s willing to admit that he has.” She believes that he developed the disorder around the time that his father died and notes that the siblings have commented on his tendencies for years. Among these is an obsession with the number seven, which is the number he counts to as he obsessively cleans the phone, every area of the bathroom, and other areas with which he comes into frequent contact.

“I’m just super-organized and clean and it’s just about me feeling comfortable,” he says. “It doesn’t really affect my life.” He rationalizes that he is merely “super-anal” but explains that everybody in the family is like that. “We just don’t talk about it.” But after Khloé and other family members call him out on this behavior, it becomes apparent that the problem runs deeper than just a compulsion to clean.

“My brother has always had, you know, levels of OCD,” Khloé says. “I think he has a bigger problem than he’s willing to admit and I believe he needs to speak to someone, but I know that’s not going to happen, because in Rob’s head there’s nothing wrong with him.”

After a worrisome incident while driving, however, Khloé finally convinces him to seek help. We see him call a psychotherapist to find out what’s triggering his issues. “I think I have some type of, I don’t know, OCD or something,” he tells the shrink.

After he explains what’s going on, the therapist tells him that it sounds like “pretty classic OCD.” He believes the problem is fairly mild but tells Rob that it “can escalate if you’re stressed out” and recommends treatment.

It’s unclear whether Rob ever followed up on the suggestion, but within a few months, it was clear that his problems had indeed escalated. In December 2011, the New York Daily News had reported that Rob was launching a line of dress socks with “funky, colorful, cool designs.” But months later, there was still no sign of the venture. While his sisters seemed to launch a new scent or clothing line every month, Rob’s socks were nowhere to be seen. He had made it clear that he wasn’t planning to launch the enterprise as part of the Kardashian brand but that he wanted to keep them separate.

By the time season 7 of Keeping Up with the Kardashians aired, however, we discover that he is bitter about the fact that his mom and sisters are not doing enough to help him launch his sock line. His frustration comes to a head in an episode aired in August, when Oprah Winfrey is scheduled to interview the family. In the van on the way to the interview, he tells his sisters, “I don’t have anything coming in. I mean, I have the sock thing.” He mentions that he wants to open up a menswear shop with Lamar but nobody will support him. Kim dismisses his whining. “Rob, you’ve proved you’re flaky, so they’re not going to work with you,” she says. “I literally have no income,” he replies.

When the queen of talk shows arrives, Rob is asked to wait while Oprah interviews Kim solo and then his other sisters. He is told by a producer that they will interview him at “the end.” Finally, Oprah asks him if he ever feels like he is “living in their shadow.” He admits it’s “tough” but assures her that he couldn’t be happier for their success. “My dad was an entrepreneur and that’s something I want to be,” he says. “Everything they’re doing is, right, because of my mom—but also more importantly because of my dad, because he was the one who taught everybody.” Khloé pipes in, annoyed, protesting that “we work hard.”

In her confessional, Khloé says she thinks it’s hard for Rob to be compared to his sisters but says he doesn’t realize how much work she and her sisters have put into their businesses. “I don’t think Rob remembers the struggles that we had and how long it took for things to get going,” she says.

Afterward, Kim is at Kourtney and Scott’s house, where she reveals to her sisters that she has an opportunity to do her own lingerie line in the Philippines. She assures them it won’t conflict with their Sears Kardashian Kollection or other family ventures. When the girls express concern, Kim gets annoyed. “What’s wrong with me doing that? What’s wrong with me doing something on my own?”

Visibly upset, Khloé tells her that they have a long-term plan to promote things as a family. “Why are you going to taint our water by diluting it?” she asks.

Kim wonders why her sisters feel threatened by the idea of her doing something without them. She assures them it won’t affect any project she does with them. She notes that Kris will often agree to stick the other girls in with Kim’s endorsements because “she’s not paying attention half the time.” Kourtney believes it’s more rewarding if they’re all together to experience it.

Afterward, the tension from the exchange is still simmering. “I know my dad would be disgusted if he ever knew that business deals came between my sisters and I,” Khloé says. “I feel like we have a lot to say and we need a mediator and we need someone who can, like, volleyball it and make it fine.” Talking to Kourtney after their blowup with Kim, Khloé believes that the only way to deal with the “issues” is to arrange a therapy session with Kris, the three sisters, and Rob.

“We just need someone to help us get through everything,” Khloé says. “[Kim’s baby] is coming. The baby can’t be brought into all this negative energy.”

Khloé calls Kim and tells her “it’s time for an intervention.” When Kim asks her what she’s referring to, she says, “All you guys are majorly obnoxious and Robert might be OCD among other problems . . . so I think we should have a family intervention.”

Kim isn’t buying the idea. “I think that sounds like the most ridiculous idea, and I’m so not into it.” Khloé tells her that Kris agreed to go, which leaves Kim skeptical because “she’s so not into therapy.” Finally, after calling Kris, Kim reluctantly agrees to attend a family-therapy session. Like countless other episodes of Keeping Up with the Kardashians, the premise is clearly staged—one of those ideas that Kris or a producer undoubtedly conceived to ramp up the drama for the cameras. Indeed, the argument about Kim’s solo lingerie line may very well have been an infomercial to pave the way for Kim to launch a line of products separate from the family.

But when it comes time for the therapy session, it sets the stage for some rare genuine insights into the family and, more important, offers a seemingly candid glimpse of the angst and emotional dysfunction plaguing the family’s only son. While the girls are having their hair and makeup done to prepare for an interview on Jimmy Kimmel later in the day, Kourtney tells Kim that Rob wants to open up a menswear store in London.

“Is that okay with you?” Rob snaps.

When his sister asks why he’s always fighting, he continues in the same vein. “I’m asking Princess Kim. Princess Kimberly.” Kris wonders why he’s so angry all the time. “Because Kim is literally the most selfish person here and doesn’t give a fuck if I have a career!” he shouts. “All she cares about is herself. I told you this for years. Kim is selfish, obviously. She doesn’t ever want to include me in anything.”

Kim rises. “My job is to help you out? You’re not a charity case. Get a job.”

Rob fires back. “The point is you would rather hook yourself in and take me out of it because you want all the attention. ‘I want to do Oprah by myself.’ I get it; you want to separate yourself. You’re your own person.”

Kim ignores him, looking very uncomfortable.

“You can just look at her, right there—a picture is worth a thousand words. Right there, selfish,” Rob says.

“You sound like a fucking idiot,” Kim retorts.

Kris intervenes, asking everybody to take a deep breath. “I really don’t believe in therapy but seeing them fight like this, it’s probably a really good idea that we’re here,” she says in her confessional.

Soon the therapist arrives, a Los Angeles psychotherapist named Nicki J. Monti, who has appeared on a number of TV shows to help people deal with personal issues, including Millionaire Matchmaker and Love Handles: Couples in Crisis.

Kim immediately tells her that she is not crazy about therapy. “It’s just not for me,” she says. “I get it. I’m a very logical person, so if I’m acting crazy, I know all the reasons why.” Afterward, she says in her confessional, “I feel, like, after having this huge fight right before we walk into our therapy, I’m not in the mood for this and I don’t really want to talk to a stranger about my family problems.”

They tell the doctor what went on before she arrived. “Robert has a lot of deep-rooted issues,” says Khloé, “because Robert doesn’t talk to a lot of people. He shares certain things with Kourtney, certain things with Kim, and certain things with me.”

Rob says he’s not antisocial, just very private. “The only people in my life that matter is my family,” he says. “I don’t have many friends.”

“I think we as women don’t even give him time to talk,” Khloé explains.

When it’s Kris’s turn, she says she wants to come away with a “line that we learn not to cross.” She feels that they all take each other for granted. “Appreciation I think would be really cool.” Kourtney notes that appreciation goes both ways, prompting Dr. Monti to ask whether she feels that her mom favors Kim. “I think all three of us could say that,” Khloé says.

The doctor asks Kim whether she agrees.

“I feel that my mom and I have a close relationship, and I can understand her more, so I think she’s more comfortable communicating with me,” she replies.

Kris tells Khloé that she thinks she takes things too personally, protesting that she doesn’t mean any harm but that she’s very busy and it often takes a long time to get back to her kids and tell them they’ve done a good job with something.

“I don’t know why our mom finds it such a shock to learn that we think [she] favors Kim,” Khloé says afterward. “It’s just facts. And I’m obviously hurt. And to tell us that she’s just too busy—we’re not just our mom’s clients, we’re her children.”

Eventually attention turns back to Rob.

“Are they right that you’re kind of like a simmering volcano waiting to erupt?” Dr. Monti asks him. He says he speaks his mind if it’s something he’s passionate about. Kim pipes up, reminding him he does it with a “screaming voice.” Only if he’s speaking the truth about something, he insists. Kourtney tells him he reminds her of the way she used to be when she had “this anger inside.” Sometimes it’s impossible for the others to know what’s going to set him off.

“My whole thing,” he explains, “is that my anger stems from the working environment, because they all kind of put this cloud on me like I’m a loser.”

KIM: But then you blow up later.

ROB: I blow up later because when there’s a business opportunity all my mom cares about is the three girls, and whenever I say I want to open up a men’s store . . .

KIM: But mom never helped us with that.

When Dr. Monti asks him how he feels, Rob says he’s frustrated.

“You look sad,” she observes. “Am I misreading you?”

At this, he breaks down sobbing, then rises and walks away.

“Robert don’t leave,” Kris says.

Dr. Monti repeats the plea. “Please don’t leave. Stay and talk about this. Things don’t get better when you walk out.”

Kim remains silent while Khloé goes after her brother.

“It’s just sad to see him cry, because he never does,” Kourtney observes.

From the back of the room, we hear Khloé say, “It’s okay; you’re allowed to cry. I can help you. You just have to tell me what you need help with.”

The therapist joins them to find Rob still sobbing and tells him he obviously doesn’t feel “safe.” When she asks him what he wants to have happen, he says, “I just want my family happy. All I care about is saying yes to my mom, making her happy, doing whatever my sisters want to make them happy, and I feel like when it comes to the easiest things, they won’t help me.”

Meanwhile, Kim appears unmoved by her brother’s anguish.

“Nobody ever gave me anything,” she says. “When I wanted something, I worked and I made it happen. When Kourtney wants something, she makes it happen. When Khloé wants something, she makes it happen.”

When Rob continues to blame Kris for favoring the girls over him, Kim rises to her mother’s defense, saying that Kris is doing the best she can. “I feel bad for her that all of us are really mean to her (crying). I think she’s doing the best that she can, which is why I have her back because I don’t think it’s her fault. I just don’t think she knows how to raise a son that well. That was, like, Dad’s thing, and now that Dad’s not here, it’s, like no one’s fault, you know, so I don’t think any of us know what we’re doing. With our career, I think Mom and I were just lucky and made it happen. . . . I feel bad that everybody is so mean to Mom. She does what she can with the girls. That’s her thing . . . girls.”

The topic then turns to Robert’s death. Dr. Monti asks Kim what it was like at the end. “I think I handled it very well,” Kim says. “I worked in his office. I was the last one working there.”

Khloé reminds her that she worked there, too. This prompts a tense exchange between the two, with Kim suggesting that Khloé is lying.

After watching episodes of the show for weeks, the therapy session felt like the first genuine raw human emotion that I had witnessed among the family. It also left the impression that Kim was somewhat insensitive to her brother’s pain, which is at odds with the picture painted of her by others who know her. Contrary to what I had expected when I set out to chronicle the family, I found very few people who knew her who were willing to speak badly of Kim. The word most often used to describe her, in fact, was nice. My longtime friend Hardy Hill—best known as a contestant on season 2 of Big Brother—was also a longtime ambassador for Miami’s Opium Group of nightclubs. He recalls the first time he met Kim, when she was hired to work an event by the South Beach nightclub Privé around 2007, and she arrived with Kourtney and Khloé.

“I didn’t realize that they were all sisters immediately because I didn’t realize that Kim had sisters at the time,” Hardy recalls. “She was just new on the scene. She was very nice, very down to earth.” He called all three sisters very “sweet.” They were very kind to anybody who approached, he recalled. “They were not standoffish at all.” The same can’t be said for all celebrities, he notes. When he hosted Kourtney and Scott for a New Year’s Eve party years later, he said he found Kourtney once again “lovely” but that Scott was “a dick. Very unapproachable, very arrogant, very cocky and aloof and, to be honest with you, a not-all-around-good guy.”

Although I had started this book assuming Kim was a diva or a spoiled princess like her old friend Paris Hilton, I was soon disabused of the idea by just about everybody I met who had come into contact with her. Her pleasant demeanor is also an assessment echoed in a 2015 Rolling Stone article, “Kim Kardashian: American Woman.”

After Kim notes that many fans find the family’s success “aspirational,” the magazine observes, “That someone might not find the Kardashians aspirational is simply something she would not consider. She’s not conflicted about the point of life: It’s to be happy and make money, and she’s doing both. Kardashian is a nice person—there’s no way to spend time with her and not come away with that impression.”

So when we see Kim being mean to her brother, it’s likely more an example of complicated sibling dynamics than a reflection of her true personality. In 2014, she would tell talk show host Andy Cohen, “My brother and I are so close, he’s one of my best friends. I’m definitely a tough-love kind of person. If I don’t like something that’s going on in my life, I change it, and I don’t sit and complain about it for a year.”

Whatever the case, things only seemed to go downhill from there. At the end of 2012, Rob finally managed to launch his sock line, Arthur George—combining his and his father’s middle names. The high-end department store Neiman Marcus struck a deal to sell the line exclusively for $30 a pair, although the line never seemed to enjoy the success of his sisters’ more affordable clothing lines and has seen only fair-to-middling sales over the years.

The year 2013 saw Rob, once a buff male model, gain significant weight, which would become a recurring theme on Keeping Up with the Kardashians. In one episode, Rob receives the results of a blood test that has Kris openly chastising him about his weight gain.

“Your liver is shutting down,” she tells the twenty-six-year-old. “This is life-threatening at this point. You can only sustain this level of being unhealthy for so long.”

If it’s possible to pinpoint the nadir of Rob’s struggles, it would have to be the breakdown of Khloé’s marriage to Lamar Odom in 2012 and 2013, reportedly over his heavy use of alcohol and drugs and his cheating on her with other women. Although Lamar, whose father was a heroin addict, had reportedly binged on crack, Rob was, by most accounts, content with smoking pot and listening to rap music when the two hung out. According to a buddy of Rob’s named Craig Long, Lamar’s departure from the scene is the reason Rob “went wild high on drugs.” Long told me he believes Rob was lost without Lamar.

“They became best friends. They were brothers. When Lamar’s marriage to Khloé fell apart, Rob lost the only man he was close to since his dad died. He felt alone, somewhat abandoned. He got heavy into drugs and let himself completely go. I know Lamar for years, and him, too—he’s always been up and down. But the marriage to Khloé was long over before anybody really knew. That’s why Lamar also went into a tailspin, abusing drugs and alcohol like you can’t imagine. It got messy.”

When Kim married Kanye in May 2014, Rob was a conspicuous no-show at the wedding, despite the fact that he had flown to Italy with the rest of the family to attend. After rumors of a blowup with his sister surfaced, Kim set the record straight. “He sent me a long email the morning of, that he was going to leave,” she explained. “There was no fight.”

A few months later, it appeared as if they were anything but best friends after he notoriously posted a photo to Instagram of Rosamund Pike’s blood-soaked psychopathic character from the movie Gone Girl and labeled it: “This is my sister Kim, the bitch from Gone Girl.”

Eventually reports began to circulate that Rob was struggling with severe depression or had entered rehab. Soon he stopped appearing in episodes of the show altogether, reportedly because of anxiety over his severe weight gain. He even disappeared for an extended time from social media, which, as with the other siblings, is an important source of income for him. In a 2015 episode of Keeping Up with the Kardashians—in which he is shown only in flashbacks—Khloé takes note of Rob’s retreat from public life.

“If you’re out and photographed and people rag on you and talk about you, it only gets you into this deeper, darker hole and you just don’t want to be seen anymore,” she explains. Later, Kris expresses her own anguish. “As a mom, it breaks my heart to see him go through what he’s going through. He’s kind of stuck in a really bad place and I just want to help him get out of it.”

In the episode, we see her talk on the phone to somebody to whom she hints that Rob has a serious problem. “I just think that as a family we have to do something immediately,” she says.

It emerges that she has contacted a “life coach,” who has an entire team to deal with people in crisis. She wants to bring him in to work with Rob, she tells Kim. “I feel that if I don’t do something drastic, then he’s going to die,” she says ominously. We see the family meet with the coach, but without Khloé, who Kris explains has been excluded because she’s a little too protective of her brother and might not think it’s a good idea.

“He was always someone who was very athletic growing up, and he’s gained over a hundred pounds in the last year,” she tells the life coach, before breaking down in tears. “He doesn’t want to participate. He doesn’t go out of the house. He’s missed Christmas, he’s missed Kim’s wedding.”

Kim interrupts. “He obviously has some kind of depression.” When Kris explains that he keeps procrastinating about getting anything done, Kim puts in, “He is the king of excuses.” Kourtney explains that everybody has been overcompensating for him since Robert died when he was sixteen. “I don’t know if it’s because he has it so easy, but then also at the same time with what he’s going through, I don’t want him to feel even more alone.”

Kim adds, “I’m the only one that’s really tough with him, so he probably avoids me the most.”

The coach suggests bringing somebody to the house to make sure he’s stabilized, “bring meds in and make sure he’s comfortable.” Sounding as though they are considering committing him, or the equivalent, Kris says, “It’s like you’re just waiting for this horrible thing to happen and there’s nothing you can do about it.”

When Khloé eventually discovers what has been happening, she accuses her family of “ambushing” both Rob and herself. Rob has been living with her, so she believes she knows what he is going through better than Kris or her sisters. She notes that they haven’t bothered to visit him for days. “Do you even know his daily routine?” she asks, noting that there are other things they can do before taking such a “drastic” step. She predicts the intervention will simply leave her brother agitated.

Kris protests that she calls him on a daily basis and gets “rejection on a daily basis. We’re all trying in our own way,” she tells Khloé, who finally agrees to allow the intervention at her house.

When the time comes, Khloé reveals that Rob has announced he is locking himself in his room and doesn’t need any help. “He said this isn’t the right way.” Kim is visibly annoyed. “You just need to say, ‘You’re kicked out of the house, you’re cut off, your bank accounts and your credit cards are closed. You do not have a dime,’ ” she tells her younger sister.

KHLOÉ: I can’t kick him out of my house.

KIM: Yeah, you can. That’s what you have to do.

Later, when Kris invites Rob to stay with her, Kim gets annoyed again: “Now, what we have to do is everyone back off. Everyone licks Rob’s ass and does whatever he says and at some point you just have to give it up. . . .We all make his life so easy. ‘Okay, we’ll drive you around with the chauffeur so no one has to look at you. We have a chef on standby, a trainer; we have someone to run out and buy you socks and underwear.’ This is pathetic. We are not going to cater to him anymore, but it has to be all of us.”

The episode ends with no resolution, and Rob has continued to stay for the most part out of the public eye. It’s fairly obvious to me that this isn’t the usual Kardashian family drama designed for publicity or TV ratings. Yet it’s easy to trot out clichés to explain Rob’s emotional spiral as the price of fame. In the Miami Beach complex where I live, one of my neighbors happens to be Eva Ritvo, a psychiatrist and TV personality in her own right who has treated many celebrity clients. I asked her to give me a sense of Rob’s issues, notwithstanding the fact that she has never met him.

“The Kardashian family is female-centric,” she explained.

Although both Robert Kardashian and Bruce Jenner were powerful figures, it appears that Kris is more powerful when it comes to family dynamics. Kris has run a multimillion-dollar operation successfully for the last decade. Although some criticized her for monetizing her family members, she has certainly been successful in her mission. Her daughters and grandchildren will not have to worry about money, and how many women can say they achieved that? Rob seems to be the family member having the most difficult time with the unusual family lifestyle. He has struggled with weight, depression, and substance abuse. The constant scrutiny of the public eye is a strain, and it is remarkable how well the girls seem to handle the stress. They have leveraged their fame to date and marry high-status men and to create professional success via modeling, book writing, and retail businesses. Rob too has tried to monetize his success with a sock company but seems to have succumbed to the stress, as evidenced by overeating and turning to drugs to alter his mood. Many celebrities fall victim to drugs and alcohol as a way to cope with the chronic cortisol released by the stress of being in the public eye. Depression, obesity, and substance abuse are all medical conditions that should be treated by mental health professionals. With access to the best of everything, I hope that Rob can tap into the proper resources and overcome the obstacles he has faced. Family support is often vital to combating mental health issues, and it would be important that the family stay close and aid him in his recovery. Monica Lewinsky beautifully describes the role of her family in helping her overcome the shame of cyberbullying. Rob’s family must similarly bond together to assist their seemingly weakest family member. As my dear mentor, Robert Michels, once said, “A family is held hostage to its sickest member.” We often hear, “A mother is only as happy as her least happiest child,” and in Kris’s case, I imagine that this rings true.

As it would turn out, Rob’s emotional turmoil wasn’t the only family crisis Kris was dealing with.