Sascha Bailey: I nearly became a woman

The art curator Sascha Bailey is wearing his “lucky suit”, a razor-sharp charcoal grey two-piece that the 29-year-old former model — the son of the fashion photographer David Bailey and the model Catherine Dyer — had on when he fled his former life in Japan at the end of 2022.

The suit was also his go-to attire for keynote events in the country’s digital art world, in whose dizzying expansion Bailey was a player. “I had done the opening for an exhibition the night before,” he tells me over Zoom as he draws on a cigarette — Bailey is the kind of tall, attractively sallow, angular person who makes smoking look aspirational and peroxide hair seem suddenly viable for the over-25s.

“I built one of the biggest shows in Asia,” he says, jolting me from my reverie. Indeed, he ran the international sales platform Blockchain Art Exchange, attracting an admiring press locally and abroad as a pioneer in the NFT (non-fungible tokens) art scene. However, behind the scenes his tumultuous society marriage to a woman ten years his senior was causing him anguish, and expat social isolation had set in — he speaks little Japanese and had moved to the country just before the pandemic. On the evening of Saturday, October 15, 2022, he decided that something had to give.

Bailey says he had little time to gather belongings from the large suburban Tokyo home he shared with his wife, the Japanese lawyer Mimi Nishikawa, and their three dogs before leaving them behind and heading to Haneda airport, where he bought a one-way ticket to Heathrow from a desk, like in the movies. “I had the foresight to pack my desktop computer in my bag. I also took my make-up and my dresses and nothing else.” Except, he adds, for his gel nails and the month’s supply of the hormone replacement therapy he had been prescribed at the open day of a specialist gender clinic in the coastal city of Nagoya.

The feminine trappings were part of Bailey’s plan to start a new life as “Sacha” without the “s” — “a statuesque blonde” with pneumatic, surgically enhanced curves. “I don’t do things by half measures,” he says now with a sad smile. Because at the time Bailey fervently believed himself to be a transgender woman, “born in the wrong body”, a belief he has since entirely relinquished, for complex reasons we will discuss.

Bailey is intelligent and personable, and our interview takes approximately 15 times the length of his “diagnosis”. The Nagoya clinic had signed him up for gender reassignment after one meeting, a surreal process he says took less than ten minutes from start to finish. “I went and saw the surgeon, a psychiatrist popped in and we spoke over one of those translation boxes, and I had the [oestrogen] patches prescribed and everything.”

Now back in the UK and identifying as male once more, he sounds remarkably calm when it comes to the ease with which his life nearly took a very different course. “You go, you have the money and if you want to do it they’ll put you forward. The diagnosis with the doctor felt like much more of a formality than a serious requirement.”

How did it come to this? Just like the old saw about bankruptcy, Bailey says the desire to manifest as someone else entirely came on gradually, then all at once. He says he experienced something akin to “dysphoria” in childhood and believes that he was in some way predisposed to it. “But whether that was gender-based I don’t know.”

He is at pains to describe a largely unremarkable childhood rather than the sort of stately, Stephen Poliakoffesque vision of new establishment bohemia that my imagination wants to assign him. I’m not alone, apparently. “I think people want me to have had this ultra-privileged upbringing,” he says.

But there was trauma, in the form of the sexual abuse he suffered at the hands of an unnamed “older male”. Perhaps as a consequence, he says, “I often found it hard growing up to identify with males and male characters. I used to love Ripley [Sigourney Weaver’s character] from Alien because she was strong and she didn’t represent the person who had hurt me — [as a female] she looked sufficiently different.”

• I was too young to transition — now I want to help other teenagers

Education-wise, he was unhappy for the two years he spent at boarding school. “I didn’t thrive in that environment because of not being able to spell and not being very good at sports either, which is not a very good mix for private boarding school,” he says. But that life improved once he was diagnosed with dyslexia and moved to a means-tested specialist day school in London, with weekends and holidays spent at the family’s country home in Devon.

He left school at 16, after which he was signed by the prestigious Storm agency and worked as a model, walking in fashion shows for labels including Dolce & Gabbana. “Unless you’re David Gandy you’re not making a career out of it,” he says now, laughing about the income disparity that works in favour of the women. “It’s like a summer camp for young, good-looking men. It really isn’t a serious job.”

Modelling took him to Japan for extended periods, seeding the idea of moving there, which became a reality after he met Nishikawa, now his ex-wife. But the pressure of business and her expectations was a perfect storm. He says that reckless spending at home led to financial problems at his company “to the point where I actually had to sell a Damien Hirst that was signed personally with my name on it” to pay his employees. (Before moving to Japan, Bailey collaborated on art shows with Hirst’s son, Connor.) “I had five years of essentially holding up this façade of a happy couple.”

His lowest point was a suicide attempt, after which he almost immediately began to ruminate and fantasise about transitioning into a Barbie-like glamazon. He wasn’t alone. Spending more and more time in internet forums, he used a report for his own online culture magazine, FOMA (“Fear of Missing Art”), to engage with members of the “transmaxxing” subculture, individuals who say they are transitioning (typically from male to female) for opportunistic, sometimes laughably venal, reasons. The online “transmaxxing manifesto” lists the supposed advantages of womanhood as including cheaper car insurance and the option of accessing women-only positions in the highly competitive Stem sector. There seems to be a considerable overlap between professed transmaxxers and the autistic community. “It’s a form of problem-solving,” Bailey says. “When you think about [transmaxxers] you have to take away all the feelings and the internal stuff because what they’re [actually] trying to do is make themselves right for the situation.”

Bailey stresses that he was never a transmaxxer. “I wouldn’t diagnose myself as autistic but it’s true that I have something of a sequential mind in that way.” He says that he thought of transitioning to womanhood as being a “project” that he could objectively get right. In particular, he says that the prolonged experience of being “attacked at home for not being enough” left him emasculated and desperate to pin his hopes on another way of being entirely. Nishikawa, he says, affirmed the idea without any thought, although it’s fair to say this was far from the only quirk of the marriage. “She tried to make me sign a contract where I agreed that I would give her most of my money while I was transitioning and she could be with anyone she wanted, but I had to stick around and pretend not to be trans for a long time … That was all very odd too … It felt like she saw this as an opportunity rather than something she was losing.” He has published this contract on the forum Medium.

I ask how he broke the news of all this to his family back home. The short answer seems to be: selectively. Nobody overtly questioned his decision to become a woman. He says that “my mum came to collect me from the airport” after the flight from Japan and he moved back home. He wanted to line up a second month’s prescription of HRT before embarking on the regimen. Ultimately it was NHS waiting times that gave him a cooling-off period: “I wasn’t going to start because the worst thing you can do is to stop and start.”

It was during this window that he met and befriended Lucy Brown, who would become his girlfriend. “She didn’t treat me with kid gloves but talked to me like a normal person about what I was doing and why I was doing it,” he says. On one occasion, he adds, Brown “repeated back my reasoning to me and I just started laughing. It all unravelled from that point”.

Now a photographer, Brown has previously worked as an assistant to the far-right leader Stephen Yaxley-Lennon, aka Tommy Robinson, from whom she has since disassociated herself. Or, as Bailey somewhat more gauzily puts it, “she was involved with some freedom of speech sort of stuff and she has done a pivot on a lot of stuff”.

I wonder whether men’s rights is where their political perspectives coalesce. In some sense, Bailey seems to see his own experience as emblematic of a broader societal collapse that has left men with few worthwhile role models. “A lot of people are voiceless, and instead of people ridiculing them they need to be listened to.”

He thinks “it says a great deal about our society” that young men are gravitating towards some people like Andrew Tate, “just because some small portion of what he’s saying is fundamentally true. When you’re in a desert everything looks like an oasis”.

I ask who out of the previously supportive Bailey clan — which includes an older brother, Fenton, and a sister, Paloma — has expressed relief. He laughs. “Everyone. I think everyone saw that it was maybe wrong for me but didn’t want to say something.” Now, he says, “everyone has kind of breathed a sigh of relief”.

He is aware that none of this will make him very popular with those who see gender-questioning individuals as requiring nothing but affirmation. In gender terms Bailey is a “desister” — the term for someone who experiences gender dysphoria and then ultimately decides not to transition. Writing in The Atlantic, Tey Meadow, an assistant professor of sociology and member of the executive committee of the Institute for the Study of Sexuality and Gender, asserts that “to focus on desisters is to focus on the rarest of cases, and to ignore the vastly more common experience of trans teens: that of being second-guessed”.

Of course Bailey was not a teenager when he stood at the gender crossroads, but he has been watching recent developments in the field of youth gender medicine with interest. “I do think the Cass report, the WPATH leak and the NHS banning hormones for kids — these three things at once have made it a bit undeniable that there is something else going on and we need to acknowledge it.”

• Nine key findings from the Cass report into gender transition

He says that most of his contemporaries from Devon who have moved to London now identify as “gender-queer or gender-fluid” and speculates that the special status this used to confer must be in danger of going into reverse. In fact he hopes his own generation will be the one to step back from the brink of culture war, in which mutual misery is assured. “I think they can listen to people on both sides of the argument without attacking them. For my part, I’ve never said that I’m speaking on behalf of trans people. I’m speaking for myself, and I’m speaking for people whom my story resonates with.” To well-adjusted transgender people who might be reading this, he says: “I’m not saying that you made a mistake. I don’t know you, frankly.”

He swerves talk of his father, who is 86 and suffering from vascular dementia, as having somehow masterminded the great mid-century liberalisation of sex, race and class that his work has come to represent. “He would have thought at the time, I’m going to put a girl in a leather jacket and take a picture through a chain-link fence.” But his father and his family is clearly very important to him and he’s especially horrified that, had he stayed on the path to gender reassignment, he might have forfeited the opportunity to have children of his own.

What does the next decade hold? He says he’s now “of no fixed abode”, and that he and Brown are “going to be moving into a place together in the next couple of months”.

All in all he thinks that his route to desistance was actually helpful — life-saving, even. “I’ve started from zero again so it’s kind of exciting. Honestly, I feel like I’ve been through nihilism and now I’m just happy to be alive.”