Caitlyn Jenner on Donald Trump, her family and life after Bruce

A few days before the release of The Secrets of My Life, Caitlyn Jenner's memoir of her journey to transgender womanhood, she and her ex-wife Kris Jenner appeared together on an episode of Keeping Up With the Kardashians.

The series is in its 11th year, but until 2015, Caitlyn was very much in the background, depicted as Bruce and as she writes in the memoir, as “a well–meaning but slightly doddering patriarch who has no life of his own and is subsumed by the women who surround him”.

Now Caitlyn is centre-stage, giving her ex-wife a primer on gender identity while Kris maintains the rictus of someone who, for once, wishes the cameras weren’t rolling. When Kris asks Caitlyn if she will undergo gender confirmation surgery, Caitlyn flicks her hair and sucks in her cheeks. “Don’t even go down this road,” she says archly. “Because I’m not going to talk about it.”

What Jenner means, I think, is that she won't talk about it at the Kardashian kitchen table, on Kardashian time, generating Kardashian ratings and revenue. For two seasons she had a perfectly good reality show of her own – I Am Cait – for that, and now there's the publicity tour for the book.

The night after our meeting, she will be interviewed by Tucker Carlson, who replaced Bill O’Reilly on Fox News and two weeks earlier informed a transgender guest on his show that a lot of trans women are “faking” it to gain access to women in public bathrooms, which, says Jenner, “wasn’t very nice”.

Still, she will go on the show because it is her mission to convert the unconverted. “I want people who have never met anyone who is trans to have a good experience,” she says. “I don’t want to sit there and yell you used the wrong name, or the wrong gender marker.”

For the likes of Carlson, she says, “I’ve got my information to counter anything he comes up with, but I’m going to do it in a fun, joking way.”

Jenner attracts no attention in the quiet corner of a hotel bar in mid-town Manhattan. She is in jeans and a sweater, made up but not overly so, friendly, good-humoured and with a guilelessness it’s hard not to warm to.

She is a source of huge irritation to parts of the transgender community, who couldn’t have wished for a more clueless spokeswoman but who, for that very reason, may be valuable in ways someone more on-message is not.

There is a certain charm to Jenner, analogous to Donald Trump’s charm before he had any power and rooted in the same effortless boasting and obliviousness to her own contradictions. She is the beneficiary of a decade-long reality show who never stops complaining about invasion of privacy; she is a trans-advocate who voted for a president who is already undermining transgender rights; when she slips up and refers to herself historically as “a guy” and “he”, she thinks, “how can I word it better?”, but also point-blank refuses to retire references to “Bruce” or castigate others who use it.

This so-called “dead-naming” is a source of particular angst to many in the trans community, for whom use of their old names is associated with efforts to shame them. But, says Jenner, “I had a life for 65 years. OK?” Besides which, “I liked Bruce. He was a good person. He did a lot in his life. Oh, ‘he didn’t even exist’. Yes he did exist! He worked his butt off. He won the [Olympic] Games. He raised amazing kids. He did a lot of very, very good things and it’s not like I just want to throw that away.”

It is two years since Jenner came out as Caitlyn on the cover of Vanity Fair and in conversation, one gets the feeling she is still high on exposure and the novelty of living as her “authentic self”. The book, which was written with Buzz Bissinger, a Pulitzer prize-winner and the journalist who did the original Vanity Fair interview, takes a more nuanced approach to Jenner’s relationship with the person she calls “little old Bruce”.

As a child, Jenner struggled as much with undiagnosed dyslexia as with gender dysphoria, something for which, in conservative Westchester County, New York, there was “no information, no name”. All she knew was that she was fascinated with her older sister Pam’s clothes and that when she looked in the mirror, she hated what she saw.

“Throughout a lifetime, everything goes through your head,” she says. “Am I just a cross-dresser? Is cross-dressing a sexual stimulation to me, so that I’m having sex with myself? Am I gay, is that what it is?” But none of these solutions felt right.

The answer, for Jenner, was to throw herself into athletics. “I was the fastest kid in school and the reason I trained so hard for so many years had a lot to do with who I was. It made me more determined than the next guy to go out there and compete.”

Athletic success, and the public acclaim that came with it, would surely “fix” her nameless unease, but it didn’t, not even winning an Olympic gold medal in the decathlon in 1976.

Marriage didn’t work, either. Jenner met her first wife, Chrystie, while they were students at Graceland University in Iowa. They were both sheltered, she writes; Chrystie the daughter of a minister, Jenner, despite her status as a jock, someone who had at that point only slept with one other woman.

They married in 1972 and had two children, although by the time Casey, the second, was born, the marriage had disintegrated. “I use the term ‘distraction’,” says Jenner, “as in ‘that was my next distraction, my children’. And I get all sorts of hell from my kids for that. My kids were not a distraction in my life – they were wonderful – but it was a distraction from myself, from who I was.”

In fact, for the next two decades, Jenner was so preoccupied with her own unhappiness, she was almost entirely absent from the lives of her first four children, to the extent that her daughter, Casey, didn’t invite Jenner to her wedding in 2007 – something she suffered terrible guilt about, she writes, but now seems to have fully recovered from.

One of the critiques of Jenner is that her wealth and celebrity is so wildly unrepresentative of the average transgender experience – as she is at pains to point out, transgender Americans face staggering rates of poverty and violence, with nine trans women murdered in the US this year alone and “all of them were trans women of colour” – that her example is worse than useless. To speak of “authenticity” in the context of Jenner’s transition has almost no meaning, when that transition has been so cushioned by privilege and compromised by profit motive.

The book, I think, puts paid to this line. Jenner was, simply, very unhappy for much of her adult life, through her second “distraction” – marriage to Linda Thompson, a model and actor she met at the Playboy mansion, and the birth of their two children, Brandon and Brody – right up to meeting Kris Kardashian.

There are some terribly poignant scenes in this period, during which she tries to broach her gender confusion both with Linda, at one point appearing before her in a wig and dress and being met with a hideous silence, and Pam, her sister, who was more sympathetic but still panicked into silence. When Jenner and Linda went to therapy together, she heard the term “gender dysphoria” for the first time and began to understand what she was grappling with. The marriage, unsurprisingly, ended.

It would be another 30 years before Jenner was able to transition and one gets the impression her politics were a big part of the problem. During her appearance at the Republican national convention last year, Jenner joked that she “got more trouble for coming out as a Republican than I did for being trans”. It made me wonder whether, just as closeted Republicans are often virulently homophobic, her conservatism had been part of her camouflage?

“Part of my camouflage?” she says. “Hmm. That’s interesting. Was it part of me hiding away from who I was? I think it had a lot to do with growing up in the 50s and 60s, and having a World War II father who landed on Omaha beach, believed in this country, and I loved all its freedoms. I don’t like big government. The only thing that’s going to get this country out of debt is the American people. Get the government the heck out of here!”

Does she regret voting for Trump?

“No,” says Jenner, so quickly I suspect “regret” is a word she has been counselled to reject in any context. “I don’t regret voting for Trump. As far as my community goes, I realise my loyalties do not lie with Donald Trump or the Republican party. But I lean on that side. OK? Why? Because I believe in limited government, lower taxes, less regulation. Now, do I agree with the Republicans on every issue? Absolutely not. And I know – I’m not stupid – I know that they’re not as good when it comes to LGBT issues. OK? The Democrats do better there. OK?”

That would seem to be a fundamental issue, I suggest.

“But I’m not a one-issue voter. So I would rather fight the Republicans to do a better job when it comes to all LGBT issues, than fight the Democrats to lower taxes and give us less regulations out there for business.”

Trump recently rescinded federal protections for transgender students, allowing them to use bathrooms in accordance with their gender identity. “I was so disappointed,” says Jenner. “I have verbally criticised him and his administration. I did talk to him at the inauguration briefly, and I talked to him once on the campaign trail about trans issues and he seemed to be really pretty good. And then when he did the [bathroom]thing it was like, whoa.”

The reason Jenner didn’t see this coming, she says, is because in 2012, Trump allowed a trans woman to compete in Miss Universe. Now all that trust has evaporated. “Trump wanted me to play golf with him and I thought you know what? It would be a good idea to go down to Mar-a-Lago, I’ll spend four hours on the golf course with him, I’ll talk about issues, things that are affecting our community. Plus to have a 67-year-old trans girl beat his butt at golf, that’s always good, too! Humble the guy a little bit.” Jenner looks thoughtful. “But then, I thought, there’s no way I can be seen with the guy.”

When Kris Kardashian met Bruce Jenner in 1990, he – Jenner tends towards use of the male pronoun when referring to her pretransition life – was pretty washed up. His days as a TV sports commentator were over and he hadn't had a booking for a public appearance in eight years.

They met on a blind date and married within a year, whereupon Kris fired his agents, stuck his name on a line of gym equipment and thoroughly rebooted his career. They had two children, Kendall and Kylie, whom they raised alongside the four children from Kris's previous relationship, Kourtney, Kim, Khloé and Robert, the future stars of Keeping Up With the Kardashians.

The most startling revelation of the book is that when they met, Jenner had been on hormone replacement therapy for four and a half years and had a bust size of 36B. Before meeting Kris, she had been determined to transition before turning 40 and the main controversy over the book has been Kris’s suggestion – made on her TV show – that Jenner married her on false pretences. Jenner says this isn’t so and that she told Kris from the outset she had gender issues.

“Did I downplay it some? Of course I did. Because I was coming up off six years of hell, and of course I wanted to get back into the game. I’m sure I downplayed it, because I didn’t think 25 years later I would transition.”

Kris knew you had been taking hormones?

“Yeah.”

I’m surprised that wasn’t a bigger heads up to her that you were trans.

“A lot of women have that can-do attitude and think I can fix this guy. And I wanted to be fixed, to be honest with you. I wanted to get back into work. We paired up and were a great team. It was 23 years of my life. We raised wonderful children. She was an extraordinary good business person.

“I owe her a debt of gratitude for getting me out of this hole and getting me back working. It was a very mutual decision to split. I didn’t leave to go transition.”

No one reading Jenner's book could doubt the authenticity of her journey. The only cynical response I had was in the timing of the transition. Jenner had no narrative arc in Keeping Up With The Kardashians. She was a thoroughly marginalised and somewhat pathetic figure, and when she left the house, transitioning brought her the kind of attention she couldn't have dreamed of in a million years while still at the Kardashian mansion.

“Attention in terms of what?”

Getting your own reality show –

“Oh, I don’t care about that stuff! I just don’t care about another show. It didn’t even cross my mind. My intentions were number one, to calm my soul. To deal with this issue and be myself. This woman had lived inside me for 65 years, it’s time for her to live! Let’s give her a shot and see what she could do. Bruce has done everything! Had all his children, won the Games. This woman – it’s her turn! And that platform I have: can I make a difference in the world?”

There wasn’t a tiny part of you that wanted to upstage your ex-wife?

“Upstage her? No. I just wanted to be me. Kris is a good person – we’ve had our differences, especially now – but she saved my life in so many ways, she turned my life around.”

“She made you lots of money, let’s face it,” I say and for the only time in the interview, Jenner looks annoyed.

“Yeah but I don’t care about money. I’m not a money person.”

After the marriage ended, Jenner told her business manager, “OK, I’m playing in the fourth quarter of life and for the last 25 years, I haven’t done anything for myself. I will enjoy this money.” She bought a “few little toys” – a nice “3,500 sq ft house on top of a hill in Malibu with a great view, not some mansion of a monstrosity like all my kids live in. It’s a humble little place. I bought an airplane, just a small one, because I’ve always been into aviation and Kris didn’t like that, so I’d been out of it for 15 years. I bought a couple of little race cars.” She shrugs. As she says, she’s not a money person.

Did Jenner regret not having transitioned at the age of 39, giving herself 25 more years of life as she was meant to live it?

“No. I have no regrets.”

“You wouldn’t have had the Kardashians,” I say.

“Well, that’s not part of it, your soul, and being happy,” she snaps. “This is the deal: it’s very simple. It wasn’t time. The issue wasn’t where it is today. I had just a few minor things done to make me feel better about myself, and I thought I’m going to do this before my 40s – I’m not going to be an old chick. I don’t want to be an old chick.

“And I got to 39 and I couldn’t do it. For six years I had isolated myself in a house, didn’t date, didn’t go out. And I’m thinking, boy, maybe I should get back into the game. I’m just sitting here in this house, rotting away. I just don’t have the guts to do it. I married Kris with great intentions.”

The Kardashian kids have been supportive of Jenner’s transition, particularly Kim, although they were upset when Jenner excluded them from her first TV interview with Diane Sawyer two years ago. Jenner thought including the Kardashians would make the whole thing look like a “big joke”, so used the adult children from her first two families instead.

Since then, there has been no stopping her. She has become assertive on the issue of women’s rights, realising that, “in so many cases, women underestimate their power. They’ve been brainwashed growing up, being the girl, they’re supposed to be in the background and all that stuff. I don’t see that. I didn’t come to womanhood that way, by sitting in the back. OK?” As a result, she says, “I like to encourage women to be more powerful and stand up for yourself.”

I suggest that Jenner’s assertiveness as a woman is partly rooted in having lived her life to the age of 65 as a beneficiary of male privilege.

“Yeah!” she says cheerfully. “I would agree with that. I know the other side. I’ve been there all my life. But I want to use that to my advantage.” This is so honest, I’m somewhat taken aback. She goes on, “Some of the criticism that my community has had is that I’m white, I’ve got money, I’m privileged and all that kind of stuff. I get that. OK?

“Can’t do much about being white. Kind of born that way. Privileged? Yeah. I’ve worked hard all my life. I’ve tried to be as smart as I can and yeah, I’ve been successful from that standpoint. And I’m not going to apologise for that.” She chuckles. “Not even close.”

To Jenner, “privilege” means having worked hard, and we hit some confusion around definitions of gay and straight, too. When I ask about her ambivalent response to gay marriage – Jenner is fully on board, now, but caused a lot of trouble on Ellen a few years ago by saying, reluctantly, “If that word ‘marriage’ is really, really that important to you, I can go with it,” – one gets the impression this is a difficult area for her.

“Um. Yes. I’ve always been with other women. I think I say in the book that if I were to go through gender confirmation, I don’t know what my future would be.” I ask if the word lesbian – which I sense is problematic for Jenner – is appropriate and she seems to think I’m asking her whether, before her transition, she was attracted to men and says, rather quickly, “sexually, I was heterosexual. Was that a high priority – in what the public perceived to be this male, Olympic stud? Not even close.”

I mention all this because for the second half of our interview, it feels to me as if I’m interacting with an ego that, to use the language Jenner herself eschews, has been thoroughly socialised as male, to the extent that – and I apologise for this – after the interview, I inadvertently refer to her with the male pronoun, having to that point, and as is correct, referred to her exclusively as “she”.

This does not undermine her journey, or the journey of any other trans person. But after hanging out with Jenner, it is impossible to avoid the sense that she is still deeply vested in the spoils that came to her as a result of the outward signifiers of her pretransition life.

Anyway, she says, she is not interested in sex. “I’m more excited about fighting battles for our community than I am about going out on a date.” Poor old community. It’s impossible to tell if Jenner does more harm than good, but if we are all, at this point, permitted to be the sole determinants of our own identities, then Jenner has the right to define herself precisely as she pleases.

“It was hard giving old Bruce up, in a lot of ways,” she says. “He still lives inside me. I still do a lot of the things old Bruce used to do. I still fly airplanes and go race cars once in a while. I can have the best of both worlds.”

She bestows on me her most dazzling smile. “I can live my life authentically, and still do all the fun stuff!”

Guardian Service. The Secrets Of My Life by Caitlyn Jenner is published by Trapeze