We all know parents aren’t supposed to have a favorite kid, and if they do then they definitely shouldn’t announce it to the world. Well, apparently no-one told Caitlyn Jenner. Because the famous reality TV star recently revealed to the media which of her children she’s closest to. And when you consider that Caitlyn has six biological and four step-kids, you realize she has plenty of options. So which of them could be the chosen one?
Caitlyn Jenner is one of the most recognizable transgender women in America and perhaps the world. She was formerly Bruce Jenner – and was well known both for her sporting achievements and having married into the Kardashian family. You may be aware of their little-known show Keeping Up with the Kardashians? She announced her transition and her new name in April, 2015, and the global audience watched her brood react to the news.
Pre-transition, Caitlyn had six children with three different women. You’ve almost certainly heard of Kendall and Kylie Jenner, her daughters with Kris Jenner (formerly Kardashian.) But before that there were Cassandra Marino and Burt Jenner, whose mother is Chrystie Crownover, and sons Brandon and Brody Jenner, the children of Linda Thompson. It’s quite the family tree.
And that tree grew even more branches when Caitlyn married Kris and became a parent figure to her four kids. Perhaps you’ve heard of them: Kourtney, Kim, Khloe and Rob? Their biological father Robert Kardashian, a lawyer and a celebrity in his own right, had split from Kris before he passed away from cancer back in 2003.
Movingly, Caitlyn reportedly promised Robert Kardashian that she would always take care of Kris’ children. So there’s a pretty strong bond. Avid watchers of reality television, though, will know that Caitlyn’s relationships with the Kardashians have had their ups and downs. And that’s putting it mildly. But what about her biological kids?
Well those have sometimes been turbulent relationships too, especially taking into account the gender transition. In 2017 Caitlyn told Diane Sawyer, “Some [of my children] I have remained very close to. A couple of them … I’m a little more distant.” So clearly the story of who’s her favorite child is a complex one.
Despite everything, Caitlyn has a good relationship with most of the Kardashians… apart from Khloe. Things between them have been bad for a while. During one May 2016 episode of Keeping Up with the Kardashians Khloe told her mom about Caitlyn, “I don’t have a relationship with her. I’m done.”
Unfortunately things didn’t get much better from there. Because in November 2019 Caitlyn went on the reality show I’m A Celebrity… Get Me Out Of Here! and talked about her children. Her son Brandon, she said, was fully supportive of her transition. But Khloe, “for some reason was [annoyed] about something through this whole process.”
Caitlyn went on, “It’s been five or six years and I really haven’t talked to her since.” When asked, “Do you think she’s more thinking about herself rather than you?” she answered, “I don’t know, we were really close. I raised her since she was five-years-old, I really don’t know what her issues are.”
Things did seem to improve though. In 2019 Khloe said on the podcast Divorce Sucks! that, “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 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.’”
The Kardashian side of the family has had many arguments with Caitlyn – very painful-sounding ones that made it seem like she would be excommunicated forever. And yet surprisingly she hung on. Even more surprisingly the relationship appeared to be fixed in private, rather than in front of the cameras. Well that’s refreshing!
In October 2019 Caitlyn celebrated her 70th birthday, and fans saw some unexpected messages on her social media feeds. Kourtney wished her a happy birthday, and Kim wrote a message that sweetly said, “I love you forever.” Both women were present at Caitlyn’s birthday party as well.
Then there’s Caitlyn’s relationship with Rob. In 2017 Caitlyn co-hosted The View and talked about a recent controversy involving him. She said he was “stupid” for leaking photos of his girlfriend, and added, “I haven’t really had a serious conversation with [Rob] in years.” She had never met his child, either.
However in 2020 Caitlyn spoke about her stepfamily again, when it was announced Keeping Up With the Kardashians was to end. She told the show Entertainment Tonight, “I talked to all the kids. I talked to Kim yesterday, I talked to them, and they have done such a magnificent job in taking that show and building their own careers outside of the show.”
And of Rob specifically she said, “Rob was an integral part [of] the show. He’s kind of stayed out of the limelight for the last few years, which is fine, it’s his own prerogative… I have seen him a lot, and the times I’ve seen him, he’s been doing much better. I’m happy for him.” That was good news. But how were her relationships with her biological kids?
Well, Caitlyn confessed that she was frequently an absent parent to her four eldest kids. Part of this was because she was struggling with her gender identity, and experiencing the mental health issues that come with that. But in a 2017 ABC News interview she acknowledged, “There’s no excuse for not being a good parent, no matter how many problems that you have.”
Coming out to her biological children was difficult for Caitlyn, but not as difficult as it might have been. Because some of them already had an inkling of what was going on. And when Caitlyn broke the news, lots of emotional floodgates opened. Brody Jenner, her son with Linda Thompson, had only seen her a handful of times through childhood, you see.
The former Olympian talked about the issues in her 2015 coming-out interview with Vanity Fair. She remembered that after she had come out to her son Burt, he told her, “To be honest with you, I think Caitlyn is a lot better person than Bruce.” She believed he was right, because “Bruce always had to tell a lie.”
And the four older Jenner kids spoke to Diane Sawyer about Caitlyn and her parenting in 2015. Brandon Jenner said, “I feel like I’m getting an upgraded version of my dad, of a parent.” And firstborn daughter Cassandra remembered that when Caitlyn came out, “I just held his hand and I cried with him and I just told him how proud of him I was and how inspired I was.”
But of all the Jenner kids, the ones that were by far the most in the public eye were Kendall and Kylie. And they ended up releasing a joint statement to ABC News about the gender transition. It read, “We love our dad very much as he is an amazing father. We couldn’t ask for a better dad. He has the biggest heart and all we want for him is to be happy. If he’s happy, we’re happy.”
Of course, things have changed a lot since 2015. Both Kendall and Kylie have grown up, and while doing so they were in the spotlight constantly. These days Kendall is a much in-demand model, and Kylie runs the make-up company Kylie Cosmetics. And they’re both massive social media stars, as you’d expect.
Just like the rest of the Kardashian-Jenner clan, the relationship between the sisters has been all over the place. Kendall admitted in the past that she was once jealous of Kylie, who was the more social one growing up. However, when Kylie became a mother in 2018, the two of them grew closer together.
And the two of them seem to maintain a good relationship with Caitlyn. Speaking on the podcast The Skinny Confidential Him & Her in January 2021, the older woman said that she admired Kendall and Kylie’s work ethic. Why? Well, Caitlyn said herself that she’d “never been much career motivated.” Perhaps the Olympian thing was just a passing fancy, then.
Both girls have spoken about Caitlyn’s impact on their lives, however. In June 2020 Kendall told People magazine, “When my dad came out as transgender, our relationship grew. She could finally be honest with me. We could talk about deep emotions she was feeling through that time. Growing up my dad was not usually one to talk about her feelings so that was a big step for us.”
Kendall emotionally went on, “Because of my dad’s bravery, I’ve learned to love what I love and not be ashamed of it. She’s been my role model since before I can even remember, from sports growing up to now with her wisdom. She’s so brave and I aspire to be as brave as her one day.”
And yet it appears that Kylie is the favorite child of all. When speaking to The Skinny Confidential Him & Her podcast in 2021, Caitlyn let it slip. She said that although Kendall and she had “a lot in common,” and she “[got] along very well with the two of them,” ultimately she and Kylie were “closer most of the time.”
Caitlyn went on, “Kendall’s off kind of doing her thing, and Kylie, like, I had dinner last night at Kylie’s house. We try to do that once a week, once every two weeks. I go over there and she always has these great meals – prepared, she doesn’t do them… But they’re so good! It’s better than a restaurant.”
Sometimes Caitlyn’s good friend Sophia Hutchins would join them for these dinners. Caitlyn said that the three of them would, “have a glass of wine and talk about stuff and this and that. And so from that standpoint, we’re a lot closer.” She added to The Skinny Confidential Him & Her podcast, “Kendall’s not that – she’s always very kind of a little bit more secretive.”
Caitlyn went on to explain that although she and Kendall were “still very close,” her older daughter “was kind of harder to figure out, where Kylie’s more of an open book.” And then the reality TV star added on, “Kylie is just the exception to the rule. I mean, she’s just – all the stars came together.”
Not all Keeping Up With the Kardashians devotees responded well to that interview. In fact, plenty were unimpressed with Caitlyn for seeming to favor one daughter over the other. On the Reddit forum for fans of the reality show, a whole thread sprung up to defend Kendall against the apparent slight.
The original poster (OP) wrote, “Caitlyn basically publicly said ‘I have a favorite and Kylie is God’s gift to this Earth and Kendall is, meh’. Any kid who has to deal with this kind of blatant favoritism for their other sibling would be angry. I would be angry, and most people with feelings would be angry and hurt too.”
Lots of people agreed in the comments. Another person wrote, “Honestly, though, Kendall is in the same boat as Caitlyn’s other kids. You can tell Brody still harbors major resentment towards Caitlyn because she’s a [bad] dad. I thought with her transition and becoming more authentic with who she is, it would bring more peace to her life and family, but I think she’s more selfish.”
Another commenter weighed in with, “Good post OP. Reminded me of that episode where Kendall is spending the day doing sporty things with Caitlyn, and all Caitlyn can do is lament about how Kylie didn’t come, and calling Kylie. Kendall was bothered as she was there and present with her dad, yet her dad was just focused on Kylie and Kylie’s lack of presence.”
The website Screen Rant hopped onto the story as well. And its article concluded, “While it is okay that Caitlyn has a closer relationship with Kylie, it is insensitive of her to speak so openly and publicly about the comparisons between the two relationships. It would not be surprising if Kendall began to distance herself even more from the family now.”
If Caitlyn was aware of the criticism she got for that interview, she hasn’t responded to it. She did however pop up in one of Kylie’s videos come February 2021 and again demonstrate that close bond she referred to. In the vid, Kylie did Caitlyn’s makeup for her, the first time she’d ever done so publicly.
The two of them talked while Kylie applied the makeup. And Kylie said to Caitlyn, “I wanted to ask you. I know, like, sometimes people get really confused when Kendall and I still call you ‘dad.’ I know we had a talk a few years ago, and you were okay with us still calling you ‘dad.’ How do you feel about that now?”
Caitlyn answered, “I feel it was one of the best decisions I made, and sometimes this community can be pretty tough, especially when it comes to pronouns and everybody’s got an opinion. I really felt from the beginning that I’ve gotta do it my way that works for me and I think everybody out there has to do it their way.”
Then Caitlyn complimented both of the sisters by telling Kylie, “You always say, ‘my dad, she,’ and that’s tough to kind of change the pronouns of it right in the middle…You guys are so good…Every time I hear it, I go, ‘my girls are on it.’” So that was a sweet family moment there.
And there doesn’t actually seem to be any animosity between Kendall and Caitlyn. In February 2021 she was spotted going out to dinner in Malibu with her father and Sophia Hutchins. According to the Daily Mail newspaper, “Before parting ways in separate vehicles… Kendall could be seen giving the former Olympian a big hug.”
To be fair to Caitlyn, she did say on the podcast that who her favorite child was, depended on the day. She explained, “I had six biological, four step. It’s a lot of children. [And] 18 grandchildren. It’s kind of just which one’s on my good side!” So maybe one of the others will get a turn before too long.