Caitlyn Jenner does not turn on her video for our Zoom interview, which surprises me. Jenner does not strike me as the kind to shrink from the limelight, any limelight — any opportunity, really, to be seen. She’s the 73-year-old former Olympian, the gold medal-winning decathlete Time magazine once described as “the world’s greatest athlete”, who rose to an entirely other kind of fame in the late Noughties and early 2010s as second husband to Kris Jenner of the Kardashian empire. Caitlyn Jenner — who at that time still lived as a man, as “Bruce”, a fact she embraces and references a lot, never mind that invoking your past, your pre-transition name and gender, is considered deeply unacceptable by the trans community, an offence called “dead-naming” — was part of the regular cast of blockbusting reality TV show Keeping Up with the Kardashians.
Jenner existed as an Eeyore-ish foil to the endless dramas perpetuated by Kris and by Kourtney, Kim, Khloé and Rob (Kris’s children by her ex-husband, the lawyer Robert Kardashian), and the two daughters the couple have together (the gawky pre-teens who would become the supermodel Kendall Jenner and the beauty entrepreneur Kylie Jenner).
If Jenner, as Bruce, was something of a background artist to the roiling scandals and love affairs, the celebrity marriages, epic break-ups, infidelities, pregnancies and infertility struggles that played out in the show, all that changed in 2015, when Jenner stole the Kardashian scene definitively. In April of that year, Jenner came out on television as a trans woman to the interviewer Diane Sawyer, saying she’d experienced gender dysphoria for her whole life and that “for all intents and purposes, I’m a woman”.
That interview was followed by a Vanity Fair cover shoot and interview (cover line: “Call me Caitlyn”), and About Bruce, a two-part Keeping Up with the Kardashians special, during which she prepared the children — all of whom were by now adults — for her transition. So it was that Jenner wound up with the biggest storyline of the entire show, which would run for six more years and cover the tumultuous demise of Kim Kardashian’s marriage to the musician and controversialist Kanye West, among other things. Even so: Caitlyn’s plotline overshadowed them all.
Yet here she is, shrinking away from my little gaze on Zoom. Maybe I’m not a big enough audience. Or maybe the prospect of my analysing her face and body — both extensively, expensively made over by cosmetic surgery procedures (she completed sex reassignment in January 2017) — is too exhausting for her.
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We start with gentle chitchat about the weather. She’s in Malibu where “on the beach, it’s 75F and clear, which is… We get a lot of fog here, so it’s a good thing.”
I’m in London, I say.
“Ah. London is London,” Jenner says.
Can’t argue with that.
She and I are to talk about her involvement with House of Kardashian, a three-part documentary about the family, for which Jenner has been extensively interviewed and, I have to say, it’s phenomenal. In-depth, slow, exquisitely edited; a classy gig with Succession-imitating intro music and acres of candid, deeply revealing footage: Bruce the extraordinary athlete and buff hunk in the Seventies; Kris the doting mother and lawyer’s trophy wife in the Eighties.
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It’s the opposite of the jarringly hectic, shamelessly shallow reality show that made its subjects famous: an engrossing, fascinating portrait of a family about whom you may swear you could not care less, of whose very existence you frankly despair, but whose cultural impact and economic might are undeniable (their combined fortune is estimated at more than $2 billion, $25 million of which — some £20-plus million — is Jenner’s).
My favourite segment covers the death of Nicole Brown Simpson and subsequent trial of her husband, OJ Simpson, for her murder. Simpson is represented by his old friend Robert Kardashian — by that point, Kris’s ex-husband. Kris, who had been close to Nicole in life, is clearly distraught in the footage. It’s a side of her you’d never otherwise see: actually candid, as opposed to TikTok-friendly faux-candid; vulnerable, grieving, furious, flanked by the pretty, anonymous children who in time will make Kris her fortune.
At the same time, precisely because of this kind of content, House of Kardashian is deeply exposing for the family, none of whom participated in it. None, that is, apart from Jenner, whose insider perspective makes the film a much weightier, more convincing proposition than it might have been otherwise.
Why’d she do it?
“Well,” she says, “I am pleased to be involved. They had the production company call Sophia [Sophia Hutchins, socialite, TV personality, founder and CEO of sunscreen company Lumasol], who is kind of my manager and runs my life. She said, ‘They’re doing this series on the family.’ I said, ‘Oh, that’s nice.’ ‘And they want you to be on the show.’ At first, I was kind of wondering, I don’t know if I should do that.”
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What were your concerns?
“My concerns, always… I’m very, very proud of all my children. My kids are just amazing. Not just the ones you see on the show. I’ve got ten children — six genetic [two by each of the wives to whom Jenner was married before Kris: Burt and Cassandra by Chrystie Crownover, and Brandon and Brody by Linda Thompson], four stepkids. I have 22 grandchildren; 23 is on the way. I always want to make sure that they’re represented the right way. I mean, it’s very difficult when you’re in public life and in the media, especially the Kardashians… Sometimes it’s just very disappointing to see how they’re represented. And when they approached me about doing this show, once I thought about it, I thought, ‘You know what? I want to get involved. I want to do my best to be very positive and really represent the family and the kids in a positive way.’ ”
Did she consult the family before saying yes?
“No. I pretty much made that decision on my own. I just thought that was the best way to do it.”
Has she spoken to them about it since? The opening ten minutes of House of Kardashian alone show Jenner pause then laugh when asked about the experience of working with her ex-wife; another interviewee calls the Kardashian women “agents of the patriarchy”; a third says, “The Kardashian brand is about making you feel shit”; yet another alludes to claims that the 2007 leaking of a sex tape made by Kris’s second daughter, Kim, and her boyfriend at the time, the singer Ray J, might have been less a malicious act by an unknown hacker and more a considered move by Kris Jenner, with Kim’s knowledge and permission, designed to both cash in on its distribution and amplify the Kardashian brand ahead of the launch of the reality show (an accusation Kim and Kris have denied in an Oprah interview).
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So presumably Jenner’s checked in?
“No. Not really. I really haven’t talked with them about it. I’m kind of doing this on my own. I’ve been in the media for a long time. I know how the game is played.”
Well from my watching of it, I say, it describes the birth of nothing short of an empire.
“Uh… Just a minute,” Jenner says. She muffles the mike on her laptop, but not so completely that I don’t overhear her ask a faceless, nameless representative — perhaps Sophia Hutchins? — in an edgy tone, “Can you tell me what she’s seen?” before the sound is fully switched off.
She returns after a few seconds.
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“It is, like, probably, no other family in history has done something like this.”
To be fair, Kris Jenner could be as flattered as she is appalled by House of Kardashian. As ruthless and manipulative as the doc, at points, suggests her to be, it also shows her as formidable. Self-made, driven, smart, extremely hard-working, a uniquely talented and wily manager, one capable of recognising an opportunity — literally any opportunity — at 200 feet; charming, attractive, great company.
When Kris came on the scene in 1990, Jenner was living a solitary life, having gone through “six years of really not even wanting to work. Kris, when we met, was basically a housewife in Beverly Hills.” Friends set them up on a blind date. “We hit it off right at the beginning, and we were married after five and a half months.”
Was it love at first sight?
“I was infatuated with her, because she was very different from me. But yes, I’d have to say, it was love at first sight.”
Kris picked Jenner up, shook her out, turned her around, professionally as well as romantically. She fired Jenner’s manager — “took over my business” — reinvigorating the speaking career with which Jenner had dabbled since retiring from athletics, then breaking her into the lucrative world of television infomercials — those inexplicably mesmerising adverts used to flog anything from lawn strimmers to at-home exercise concepts. Kris would, in time, join Jenner in the infomercials, creating a sort of beta model of a charming, funny, messy, compelling, heavily monetised TV family unit. And so the seed of a plan for a billion-dollar-generating reality TV enterprise was planted.
Were you aware of what you were part of, how huge it would become, in those very early stages?
“I had no idea what the future held for us. I don’t think even she did.”
I hadn’t realised before watching House of Kardashian that when Jenner met Kris, she was already in the early stages of transition.
Jenner cannot remember a time when she didn’t feel gender dysphoric. “You’re kind of born that way,” she tells me. “It’s not something that, when you’re 20 years old, you go, ‘Wait a second…’ ”
CAITLYN JENNER WAS BORN WILLIAM BRUCE JENNER in 1949 and raised in Westchester, New York. Her father, William, was a tree surgeon (whom Jenner has described as “maddeningly handsome”) who took part in the Normandy landings; her mother, Esther, was a housewife whose clothes Jenner took to stealing and secretly wearing when she was ten, blaming her sister Pam if her mother noticed. As a teenager, Jenner has said, she found herself “jealous” of women who could just exist as women. Much later still, when she and Kris were married, she’d experience “envy” watching Kris apply make-up.
That all sounds painful, I say.
“You learn to live with it. And I did — I think I did a good job of living with it. Living a great life. Before I met Kris, I had six years from, like, 1984 to 1990, when I was really struggling with my identity and who I was. I certainly had done a few little things to try to cope with life.”
What kind of little things?
“I was on hormones. I’d done things.” She has said she had 36B breasts by the late Eighties, which she was binding beneath baggy suits and shirts; that she’d had laser treatment on her beard to inhibit its growth. “But then I got to 1989 — 39 years old — and I couldn’t do it [fully transition]. I just couldn’t do it.”
Why?
“The only thing I can say is, it wasn’t time. Society, me — it wasn’t time. So I said, ‘I’ve got to get back into life,’ because I was living by myself in a little dinky house and barely coming out. ‘I’ve got to move on and I’ve got to get back into life.’ And about five months later, I was set up with Kris on a blind date.”
Did Kris bring you back into life?
“Oh yeah. Definitely. She was by far the best thing that happened to me.”
There is a touch of the “recollections may vary” around what Kris knew about Caitlyn Jenner’s gender dysphoria when the couple met — and indeed, over the course of their more than 20-year marriage (they separated in 2013 and divorced in 2015). Jenner claims in her 2017 memoir, The Secrets of My Life, that she told Kris all about it before they first had sex; Kris insists she did not. “I knew you struggled with wanting to dress like a female,” Kris tells Jenner in the About Bruce special, “but that’s all I knew.”
“I’m the one you lied to for the longest,” she claims. “I never saw this coming in a gazillion years.”
Oh, but Jenner then goes on to tell me, “Being gender dysphoric had nothing to do with the divorce. Nothing. There were a million other things that were going on.”
I’d assumed Jenner must have been struggling behind the scenes of Keeping Up with the Kardashians, by the schism between her (increasingly) public and private/secret selves. Not at all, Jenner says. “It was a good time! Not only did I have Kris, but I also picked up four kids in the process. I am the best at being a dad, a parent. I love that. I love kids. I love carpool. I love helping them grow up. And all of a sudden, I went from four kids to eight kids. We decided that we should some kids together, so boom, there come Kendall and Kylie and I got a full house.”
And that was a better, happier life for you than transitioning would have provided?
“Yeah. I had a lot of fun raising those kids.”
And being married to Kris?
“The marriage? It was very good.”
Is she not a bit… terrifying?
Jenner scoffs. She’s been extremely — studiedly, even — charming to this point; but there’s a cool edge to her voice now.
“No. Not at all.”
When the full force of reality TV first struck, Jenner says she was the most prepared of all the family. She segues into a Trumpian level of boastfulness on the subject. “I had been famous since 1976. I went out, beat the whole world, won the Olympic gold and was titled ‘the greatest athlete in the world’. I had seen fame at an extraordinarily big level. None of my kids, and Kris’s kids, or Kris, had. So honestly, I tried to talk to my kids a lot about fame and what it’s all about.”
What did you tell them? (Having gone boasty Trump, Jenner switches to royalty in acts of service mode.) “Don’t let it go to your head. Don’t get full of yourself. Stay humble. Be generous with other people and their time. If somebody asks for an autograph, do your damnedest — and I know sometimes they can get pretty tough — to try to oblige that. Have a smile on your face. You’ve got to realise that the public is your business. The reason you’re living a very good lifestyle is because of people and you’ve got to keep those people on your side. You know what, it’s been funny — the media has a harder time with my children than the people do.”
Does she feel protective of her children when the media attacks them?
“Yes.”
What happens? A red mist descends, you rage, try to hit someone?
“No, no. My kids today, they’ve been in the media for a long time. They know how to play the game. I always used to say, I have two lives. I’ve got my life at home. It’s kind of like everybody else. I get up, I do the dishes, I feed the family, get everybody dressed, carpool them out…”
This, I note, is Caitlyn Jenner’s second reference to “carpooling” — the middle-class, wholesome, community-spirited American tradition by which groups of parents share the shepherding of their kids to school — and she’ll make a third before our time is up. It sounds practised, as if it might be on a flash card somewhere. It makes me think of a politician trying to ensure cut-through on pre-decided messaging. Jenner’s message, in this case, seems to be one of active, doting, effective, instructive parenthood.
When I tell her how very beautiful her children are, ask if she just stares at them sometimes, she says, “I don’t know about staring at them. I’m probably giving them some advice. When you’re a parent, you’re always a parent.” And she’ll tell me it was she who counselled her children on the merits of building businesses as opposed to just being famous (two of them, Kim and Kylie, now have billion-dollar brands to their names). “I remember telling them, you can only build so much equity in yourself by doing a show… You can build up so much more equity in a business that will last you the rest of your life than you will as a celebrity.”
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She’ll wonder over Kim’s longevity: “She has been relevant in the media world for the past 20 years. And how many actors, actresses, people in the entertainment business, have been relevant for that long?” And, of course, she invokes the children — the protection of their reputations — as her official motivation for getting involved with House of Kardashian.
I try to push her off her Parent of the Year messaging a little. We discuss her decision to transition in 2015, aged 65. “I got tired of fighting it. I was just tired, and I’m thinking, ‘I’m going to die this way?’ My whole life before was lying about this.”
I ask about her chequered relationship with the broader trans community. Initially ecstatic to have such high-level, high-profile representation in Jenner, the trans world has grown wary of her over the intervening years. The ways in which she’s considered problematic include, but are not limited to: her tendency to dead-name herself; to reference “little old Bruce”; her privilege and wealth, which have facilitated extremely high-end surgery and myriad forms of support and protection denied most trans people; her outspoken conviction that trans girls should not compete in girls’ sports at school (“It just isn’t fair,” she’s said); and her out-and-out Republicanism.
At one point, Jenner was an open supporter of Donald Trump: in 2021, she launched a bid to become governor of California and during the campaign told journalists, “Obviously, I would support him,” in any Trump attempt to reclaim the White House in 2024. “I do not like what’s happening in this country right now,” she added.
So… You have a complicated relationship with the trans community, is that fair?
“I think I’m different from trans people. Yeah.”
Is it painful that they’re not more accepting of you?
“No, it’s not painful at all. Everybody’s story is different, and that’s fine, and everybody does it their own way.”
I say — honestly — that I find Jenner’s Republicanism, her outspokenness, her refusal to conform to the restrictions of identity politics, refreshing. As a classic, boring, left-leaning Trump loather, I think Jenner’s expectation-bucking convictions just make her more authentic.
“I try to be — as you put it — as ‘authentic’ as I possibly can, but I just try to do it my way. And you kind of just leave it at that. Hope for the best.”
I ask if she has any more political ambitions (she got about 1 per cent of the vote in those 2021 Californian gubernatorial elections).
“Not really. I’m just enjoying my life.”
Does she still call herself a Republican?
“Of course. I’ll always be a Republican.”
And what’s the status of your relationship with Donald Trump? I’d read conflicting reports about it, though I know they’d once been on golf at Mar-a-Lago terms. But now? Is that all gone?
“Is it ‘gone’, you said?”
Yes.
“Can we stick to the show on this, please?” snaps another voice entirely, a clipped, brusque one. (Sophia Hutchins, is that you?) “I’m not sure where this is going.”
It’s not “going” anywhere, I want to snap back: it’s a question, not a bus. Plus, I don’t think I’m exactly licking the filthy depths of tabloid intrusion asking a person who has been involved with politics if they’re still involved with politics… But fine. I ask a question that isn’t about the show at all, but is apparently more acceptable than anything Trump-related.
Is she single?
“Very single!”
How do you feel about that?
“I’m fine. I’m not even close to looking for a relationship. I’ll never have a relationship in the future. I just don’t see that in my life. I am not looking for that.”
She’s not at all lonely, she says. She has dogs (“Bertha and Baxter. Bertha: yellow lab, female. And Baxter: half black lab, half border collie. They’re probably on my bed in the other room”) and “a very large family. Every night of the week I could go to somebody’s house and have dinner.”
Anyway, she is, she says, “a relatively simple person. It doesn’t take a lot to entertain me.” Although she likes planes. “I fly airplanes. Play a lot of golf… I raced cars for 20-odd years. Racing cars is not the greatest way to make money or a career or business. You do it because it’s fun.”
She still works out? “I do. Obviously it changes from the old days. I’m not trying to win Olympic gold medals; I just enjoy good health. I don’t go crazy working out, but I get my exercise in all the time.” She also says that, though she’s no longer “obsessed” with work, she’s got one or two projects coming up.
No plans to retire?
“No.”
Caitlyn Jenner is, she says, in the “fun” stage of her life. “Wake up in the morning and be happy, have things to do — family things to do, other things to do, enjoy life.” Then again, she goes on, “There’s always another chapter. This is what makes life exciting.”
House of Kardashian premieres on Sunday on Sky Documentaries and Now
