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Divorces are hard on everybody, from the spouses breaking up to the kids who can feel caught in the crossfire.
Kourtney, Kim and Khloe Kardashian had been there before, their parents, Robert Kardashian and the future Kris Jenner first separating in 1989, when their brother Rob Kardashian was barely 2, and divorcing in 1991.
Though the exes remained friendly until Robert's death from cancer in 2003, a pregnant Kourtney told Oprah Winfrey in 2012 that her parents' divorce had put her off of marriage, making her reluctant to tie the knot with Scott Disick. Then again, after she and Scott broke up in 2015 after having three kids together, Kourtney also credited her mom and dad's enduring friendship for providing the template for her and Scott's amiable co-parenting arrangement.
"I know with my parents, as soon as everyone got along, life was so much easier. It felt like everyone was happy," Kourtney said on Keeping Up With the Kardashians last year.
But the end of Kris' second marriage was something different altogether.
Kris had married Olympic gold medalist Caitlyn Jenner, a father of four from two previous marriages, in April 1991, and they proceeded to have two kids together, Kendall and Kylie Jenner. Reality TV came along in 2007, when Keeping Up With the Kardashians premiered on E!, featuring Caitlyn—as she described in her 2017 memoir The Secrets of My Life—playing the "well-meaning but confused and helpless father and husband."
On the show, "I get love but very little respect," she continued. "I'm fine with that, because it is largely accurate."
But though the quirks of their marriage—Caitlyn hanging out while the family action ebbed and flowed around her, occasionally weighing in if her opinion was ever sought out—were on full, often humorous display, there was no inkling of the bombshell that awaited (though as some family members would later attest, they weren't entirely in the dark).
In an interview with ABC News' Diane Sawyer that aired in April 2015, the former athlete, who'd been on the cover of a Wheaties box and became one of the most recognizable faces of the 1970s and '80s as Bruce Jenner, confirmed, "Yes, for all intents and purposes I am a woman."
Fighting back tears, she said, "I've been thinking about this day forever and what I should do with my life, how do I tell my story. It's been really tough. But here I am, I'm still here. That's the good news."
Kendall and Kylie said in a statement when the interview aired. "We love our dad very much, he has the biggest heart and all we want is for him to be happy. If he's happy, we're happy."
Caitlyn watched the interview with Kris and all five Kardashian and Jenner daughters at the family home in Calabasas.
Less than two months later, the world was introduced to Caitlyn Jenner on the cover of Vanity Fair, and she's been openly living life as her true self ever since.
Which, though they were so proud (not to mention relieved that the revelation had been made so they didn't have to keep the secret any longer), this all couldn't help but be a really trying, sometimes traumatic, turn of events for her sprawling family. And not just at first.
"I have high hopes that Caitlyn is a better person than Bruce," eldest son Burt Jenner, from Jenner's first marriage to Chrystie Crownover, optimistically told Vanity Fair in 2015 (which also marked Caitlyn's official transition to using female pronouns) for its history-making cover story. "I'm very much looking forward to that."
Caitlyn, who's celebrating her 71st birthday on Oct. 28, for the most part thought she couldn't be anything but better from then on. "I think [Burt's] right, because Bruce always had to tell a lie, he was always living that lie, every day, he always had a secret from morning till night. Caitlyn doesn't have any secrets," she said.
In The Secrets of My Life, she recalled breaking the news of her transition to all 10 kids, starting with Brandon Jenner, from Jenner's second marriage, to Linda Thompson. "If I could have just stopped with Brandon, I'd be home free," Caitlyn wrote. Like Brandon, eldest kids Burt and daughter Casey from marriage No. 1 had been "told of my issues" when they were young, so they took the news in stride.
Son Brody Jenner, also with Thompson, wasn't told anything about his dad's inner life until his late twenties, so he was "shocked and stunned," Caitlyn recalled, but Brody also thought it explained a lot about his dad's emotional distance when he was growing up. (Not that Brandon didn't notice his father's absence, writing in his recent book To Me, He Was Just Dad: Stories of Growing Up with Famous Fathers that between the ages of 8 and 25 he only saw his father maybe six times. "And though I understand that she avoided the question because the answer would have laid bare too many struggles, it made my relationship with her challenging," he wrote. The question being simply, "How are you doing?")
Kim was totally supportive, Caitlyn wrote, as was Kourtney, while "Khloe [had] the hardest time with it." Jenner recalled that telling Kendall, then 19, and Kylie, who was only 17 at the time, was the most difficult step for her, though they too were ultimately supportive.
"'So, do we still call you Dad?'" Caitlyn remembered Kendall asking. To which she replied, "'Yes, I'll be your dad always.' They have called me that ever since."
In 2015 Kim credited husband Kanye West for helping her deal with the initial shock by pointing out that a person can have all the luck, love and blessings in the world, but if they're living a lie, none of it means anything. And while Caitlyn told Sawyer that Kim had "by far been the most accepting and the easiest to talk to about it," Kim admitted that Caitlyn's transition was still a "hard adjustment" and the family was in therapy together. (She was also a little miffed that Caitlyn was spelling her name with a "C.")
But that didn't change the fact that, while the six kids Caitlyn raised during her third marriage fully supported her, they had also suffered a loss. And they naturally were very protective of mom Kris, who did not appreciate Caitlyn saying, regarding the demise of their union, that "20 percent was gender and 80 percent was the way I was treated."
"We're just not a family who goes and bashes the other one publicly," Khloé said in an episode of KUWTK that gave a glimpse of the internal family backlash to the Vanity Fair story. "If we have an issue with someone, we'll go and address it to their face."
Confronting Caitlyn on the episode, Kim told her, "You said, 'Kris mistreated me.' It sounded like she beat the s--t out of you. You got the fame, but you're losing your family. It's your time, but you don't have to bash us on your way up."
Though Khloe at first said that she wouldn't go, she ultimately did join Kim, Kourtney, Kendall, Kylie, Burt, Casey, Brandon and Brody in supporting Caitlyn at the 2015 ESPYs that July, where she was honored with the Arthur Ashe Courage Award. And both Caitlyn and Kris were on hand to cheer Kendall on when she walked in the Victoria's Secret Fashion Show that November.
In fact, wounds were healing and things were looking up, Kim shared with E! News at the time, explaining, "I think for anyone that goes through this, it's not the most common thing, so I don't think a lot of people can really understand it. It's been an adjustment and it takes time and that's OK. That's normal."
Kris and Caitlyn were in "such a great place," Kim continued, "and our family is, like, totally coming back together. But I do respect that adjustment process and having to just adjust to a different lifestyle. It's our new normal and everyone is doing such a great job, we communicate really well. I think the whole family does and we're really vocal, so I think that really helps."
Thanksgiving that year was indeed a whole-family affair, Caitlyn reuniting with Kris (and her then-new boyfriend Corey Gamble) and multiple generations of Kardashians.
But while they reasonably let it be known to the outside world that how the family was coping was their business, it became apparent as the months went by that Caitlyn was becoming increasingly removed from some of her kids. (To this day she overwhelmingly refers to both her biological and stepchildren as "my kids.")
And they had their reasons.
In 2016, Kendall—who had recalled, when she was a kid, finding makeup and nail polish among her dad's things and thinking he was having an affair—revealed to Vogue that, of course, her father's transition was difficult for her to process. It "was really hard for me, because I was like, 'But you taught me everything tomboy!'" she said, but since then their relationship had returned to "super normal" and "not weird at all."
Still, she admitted wistfully, "Sometimes I look at a picture of my dad when she was a guy, and it makes me a little sad—I get emotional." But, she added, "You have to get past it—you've got a new person to love. It's kind of a blessing in disguise—if that's not the wrong way to say it."
Sitting down with Khloe in early 2017, in a conversation that was featured on KUWTK that April, Caitlyn said, "I just really feel like over the last year and a half we certainly have grown apart. Day after day after month after month, nobody calls, nobody checks in. Just, 'Hey, how are you doing?' I haven't gotten that phone call from anybody.
"You can't help but sit there and think, 'OK, is it because I transitioned? They don't like me anymore?' I want to know what I did wrong, what I didn't do wrong, what I did right, and move forward."
Khloe admitted that she wasn't on the usual Kardashian family timetable of processing one thing and then quickly moving onto the next thing that inevitably begged processing, often for the whole world to observe.
Caitlyn's physical transition got underway in 2013 (she confirmed in her book that she had gender-reassignment surgery in January 2017), and at the end of the year Khloe filed for divorce from Lamar Odom after four years of marriage, her heart not really wanting to but her head telling her she had no other choice. "I just wasn't at a place in my life where I really could invest in new relationships or even something that's this heavy," Khloe explained to Caitlyn.
And back in 2015, she continued, "it was very hard for me to experience a lot of new things so quickly, and still feeling like I have to protect my mom and certain things that were happening where I felt like they might not have been the most positive. But then I was also like, this isn't even my fight to fight anymore. I have my own s--t to deal with, so why don't you guys figure that stuff out. But I don't think Caitlyn is a bad person at all."
Khloe added that, after growing up knowing her stepfather as a certain person all her life, not having that same person around anymore came as "a huge blow, because I'm like, 'OK, my second dad, this guy that I've grown up with, that raised me, was taken away from me,' but no one really let me have that."
In her book, which came out not long after that episode aired, Caitlyn acknowledged that she was still sorting out her relationship with her kids.
"I thought transition would draw us closer," she admitted. "Initially it did. But over the past several months there has been a void, a distance, with many of them." Sure, they were all adults with full lives, and a lot of families experience the fact that, when one person is craving more time with another, it might not be the right time for that person, and vice versa at another time.
"But I worry that my transitioning has been harder for them to cope with than they have let on, because in public their support for me has been stirring," she wrote. "But perhaps there is private embarrassment. Perhaps it is weird to call me 'Dad' when I don't look like Dad."
Out promoting the book, Jenner said on Australia's Today show in May 2017 that she hadn't talked to Kim (or Kimberly, as she usually calls the second-eldest Kardashian daughter) in "a long time. I've kind of let everything calm down. So I kind of stay, you know, I keep my distance. I'm out there trying to make a difference in the world. There's a lot of drama in the Kardashian family. This is my book about my opinions on things that had happened with me and my family.
"Any time I express my opinion, you know, with my family, there's always challenges in doing that."
Kim, frankly, was unhappy about the book, mainly for Kris' sake, but also just... in general.
"My heart breaks for my mom," she told Ellen DeGeneres that April, "because I feel like she's been through so much...[Caitlyn's] promoting this book and she's saying all these things and, you know, I just don't think it's necessary. I just feel like it's unfair; things aren't truthful."
Especially with regard to their marriage, "I don't expect her to be honest about my mom now, but it's just so hurtful. Like, I just wish her all the success in the world, but not at our expense."
"I just feel like I don't respect the character that she's showing now...I just feel like there's no need for a book. Tell your story, but just don't bash other people."
Kim also said at the time, however, that it had only been a couple of weeks since she had last talked to Caitlyn.
"I'll always, always love her," she shared. "That was my stepdad for so many years. She taught me about character and so much growing up, and I just feel like I don't respect the character that she's showing now. But, like I said, I'll still always have a major love for her, for who she was in my life. I'm really sentimental; I think my mom's that way. And I'll never say...you know, it's still Kendall and Kylie's dad, so I want to be respectful, but I just feel like there's no need for a book. You know, tell your story—but just don't bash other people. I just think, like, it's not tasteful."
A source told E! News that August, however, that Kendall's relationship with her father had grown "very strained," particularly in light of Jenner's tell-all. "The more time that has passed," the source said, "the more she feels Caitlyn has let her down with the things she has said and with her actions."
At the same time, "Kylie really made an effort not to take sides and to be supportive of Caitlyn. She really wants to have a relationship with her dad, but Caitlyn has hurt Kris tremendously and it's made it very difficult." The source added, "Both girls really struggle with not being close to Caitlyn. It's left a big void in their lives to not have the father they grew up with. She was a part of their lives every single day."
Appearing on The Talk that summer, Caitlyn admitted, "I miss everybody. My house is open. My relationship with some of the kids is better and, with others, it's maybe a little more strained. But I think as time goes on, that'll change."
Each member of the family has only grown exponentially busier in recent years as more children have been born and businesses have expanded. But, happily, relations do seem to be on a more even keel.
Looking back on what they all went through, Khloe said last year (on what's now called the All's Fair With Laura Wasser podcast) that Kris was "like, Superwoman. That's also something that's a takeaway for us, in someone that we get to really look up to on that level, with just how to co-parent, how to deal with divorce and yes, I remember during the initial couple months of it, it's traumatic and her emotions are really high and that's expected...there was love there."
Moreover, Khloe added, "I saw Caitlyn recently. When I see Caitlyn, it's fine. I think we've really come a long way. It was a struggle, I think, for all of us. But as first, the transition, not because she was transitioning, I think from just how it was all handled. But I also think when your emotions die down, you're able to really look at everything and be like, 'We're all humans and we're all trying to figure this out.'"
In hindsight, she could only imagine how hard the experience was for Caitlyn.
"We all have our own s--t," Khloe said, "and I could only imagine how difficult that had to be to tell your children something like that. But at the time, information was withheld from us, and we had to find out through either media channels or other things. I think all our feelings were hurt," but now "I think we're all in a really good place and I think we all just want everybody to just be happy with whoever they are."
Kim(berly) and Caitlyn shared a hug at the Vanity Fair Oscar party in February—and Caitlyn posted a photo of them from that night in wishing Kim a happy 40th birthday on Oct. 21.
"It has been an honor to have spent the last 30 years with you," she wrote. "To watch you grow as a person, a mother, a wife, and business woman, has been the most amazing experience. PS You're catching up to me!"
When Caitlyn found out (through media channels or other things) that Keeping Up With the Kardashians was going to sign off in 2021 after 14 years on E!, truly the end of an era, she told Australia's The Morning Show last month, "Was I surprised? No, but that show...it's probably the greatest reality show in history." Over the course of 500-plus episodes, "these girls have done just an amazing job to keep the show going, come up with material."
And of course, she was so proud of all the kids.
"But kind of everybody is in a different place now and I think it's time to move on," Jenner said. "What a run."