A Trump Critic’s Descent into Trans-ness

I admired the lesbian journalist Masha Gessen. Then she came out as nonbinary.

“Using words to cover up lies, however subtly, destroys language. Validating incomprehensible drivel with polite reaction also destroys language.”

–Masha Gessen (2017)

Masha Gessen is known for trenchant critiques of power that draw on her scholarly expertise and lived experience reporting on – and standing up to – Vladimir Putin. In 2020 she started demanding people refer to her with nonbinary pronouns. Since then she’s been defending pediatric gender medicine.

I went into this research with the question: How did a serious thinker come to identify as nonbinary? After reading some of Gessen’s essays from before she was trans, my question changed. It became, Why did I think she was a serious thinker? 

This post is about nonbinaryism. It’s also about the Trump era, and how liberal rage elevated voices and ideas that didn’t really merit our attention.

A Binary, Binational Youth

Masha Gessen was born in Moscow in 1967. She says she always felt like a boy, and her parents understood that she would undergo transsexual surgery as an adult.

Her family moved to the Boston area when she was 14. They’d obtained refugee status as Soviet Jews. 

Gessen didn’t graduate from college, as far as I can tell, though she “studied at” two art schools. She described her youth in 2017:

“I was living an imaginative and risky life—I dropped out of high school, ran away from home, lived in the East Village, worked as a bicycle messenger, dropped out of college, worked in the gay press, became the editor of a magazine at twenty-one, got arrested at ACT UP protests, experimented sexually and romantically, behaved abhorrently, was a good friend, or tried to be.”

In 1991 Gessen moved to Moscow. Decamping to Eastern Europe was a popular adventure for young Americans in those years after communism disintegrated. Matt Taibbi landed in Russia around the same time. Arthur Phillips wrote a bestselling novel about the phenomenon, Prague (2003), set in Budapest. 

Compared to her fellow Americans, Gessen had the advantage of fluent Russian and cultural ease. Compared to her fellow Russians, Gessen had the privilege of a US passport and friends and family back in Boston and New York.

She also had professional connections. Over her two decades abroad, American publishers and media outlets published her journalism. The New York Times reviewed her books.

Much of her work was about Russian politics; one book was about the rise of genetic testing and her own quandary after finding out that she was predisposed to develop breast cancer. With the aim of cancer prevention she decided on mastectomy and breast reconstruction in the 2000s, and then several years later had her ovaries removed. 

By 2012 Gessen was also established as a journalist in Moscow. As the editor of a science magazine she declined to have a reporter cover a Putin publicity stunt, which got her fired. She then took over Radio Liberty, a US-backed outlet in Moscow. This soon devolved into chaos as well, according to the Heritage Foundation (which may have held a grudge against her for being a gay activist):

“Gessen, who was a consultant to RL for reorganization, managed to land the coveted RL Russian service directorship and then led the service straight into its nosedive by eliminating experienced broadcasters and bringing in with her a team of like-minded elitist print journalists, with little or no experience in radio broadcasting.”

That year Gessen published a critical biography of Vladimir Putin, The Man Without a Face.

In 2013 she moved with her partner and children to the US, citing a fear that the Russian government would take custody of her adopted son as part of a crackdown on gays.

Both her firing and her emigration garnered extensive English-language media coverage.

Female to Meh

“Nonbinary” (also known as NB or enby) is often perceived as a joke – the province of frivolous teen girls who just want attention and aren’t really going to medicalize. Public faces of the trans movement tend to downplay NB. But within the movement, it’s front and center. Queer theorists and gender doctors are all over it, because NB is actually trans in its purest form. 

The idea of existing between sexes is as old as gender medicine. In 1966, Harry Benjamin wrote in The Transsexual Phenomenon:

“Between ‘male’ and ‘female,’ ‘sex’ is a continuum with many ‘in betweens.’”

In the early 1990s the term “transgender” gained currency to describe all sorts of people who defied sex stereotypes, from post-op transsexuals to men in drag to short-haired women. Leslie Feinberg is credited (perhaps wrongly) with coining the term. She was inspired by her own transition experience – after taking testosterone and undergoing a mastectomy, she’d decided to keep living as a woman. But now she stuck out even more than she had before as a “butch lesbian,” plus she still supported what we might call trans ideology. To capture that complexity, she needed a new word: transgender.

At the same time, paraphilic men were also embracing the term transgender. In 1999 the NYT profiled one, the MTF activist Riki Wilchins. It began with hand-wringing about pronouns:

“For the sake of convenience, let it be ’she,’ and 'Ms.,' since she is a post-operative, male-to-female transsexual. But that's with apologies to Ms. Wilchins, for in her world view, such binary, he-she, Mr.-Ms. gender pigeonholing oppresses.

“'I would describe myself as a Riki-to-Riki transsexual,' she said. ‘People say I transgress gender. I don't. I'm just being Riki. It's the gender system that transgresses all over me.'”

And it got more Riki-indulgent from there.

The term “nonbinary” arose sometime after that. It appeared occasionally in the media starting in the mid-2000s, and then it took off in 2012. Teens had discovered Benjamin’s old continuum.

The New Yorker profiled an FTM kid in 2013:

“His monologue was smart, whimsical, and laden with jargon. ‘I identify as a transman, a faggy queen, a homosexual, a queer, a nerdfighter, a writer, an artist, and a guy who needs a haircut,’ he said. He revealed that he was taking testosterone while ‘presenting in a femme way,’ adding, ‘It’s nice to finally be able to have my identity be legible to people.’”

Veteran gender psychologist Walter Bockting always thought gender medicine was about so much more than “a person’s ability to ‘pass’ as a member of the other sex.” In 2019 he worried that the use of puberty blockers had led to “a renaissance of this very binary thinking.” But:

“Fortunately, at the same time, we have a parallel development of youth identifying as non-binary or genderqueer, who describe their experience no longer as a transition from A to B (male to female or female to male), but instead as ‘I’ve always been C!’, referring to a different position on the gender spectrum.”

Bockting portrayed NB as a youth movement, erasing the original nonbinary people who’d adopted the label in middle age.

Masha Gessen’s Big Break

Donald Trump declared victory over Hillary Clinton in the early hours of November 9, 2016. American liberals went insane.

On November 10, 2016, Gessen published an essay in the New York Review of Books titled “Autocracy: Rules for Survival.” Calling Trump an autocrat based on his behavior as a candidate, she drew on the authority of her lived experience:

“I have lived in autocracies most of my life, and have spent much of my career writing about Vladimir Putin’s Russia. I have learned a few rules for surviving in an autocracy and salvaging your sanity and self-respect.”

She only shared some of her rules, leaving out “maintain citizenship and employment in a different country.”

The essay begins with scorn for Clinton, then-President Barack Obama, Senator Elizabeth Warren, and Senator Bernie Sanders, because they each gave “conciliatory” remarks along the lines of “let’s try to work with the incoming president.” 

What choice did a Democratic politician have? At such a combustible moment, wasn’t it important to support the peaceful transfer of power? Gessen:

“One of the falsehoods in the Clinton speech was the implied equivalency between civil resistance and insurgency. This is an autocrat’s favorite con, the explanation for the violent suppression of peaceful protests the world over.”

In other words, Clinton fell for a grift that Trump hadn’t even launched yet. Or she was grifting on Trump’s behalf? Unclear.

What follows is a slate of bold predictions and advice:

“Trump rally crowds have chanted ‘Lock her up!’ They, and he, meant every word. If Trump does not go after Hillary Clinton on his first day in office, if he instead focuses, as his acceptance speech indicated he might, on the unifying project of investing in infrastructure (which, not coincidentally, would provide an instant opportunity to reward his cronies and himself), it will be foolish to breathe a sigh of relief.”

Trump did not lock up Clinton and he did not invest in infrastructure.

“There is little doubt that Trump will appoint someone [to the Supreme Court] who will cause the Court to veer to the right; there is also the risk that it might be someone who will wreak havoc with the very culture of the high court.”

If only! Trump pretty much outsourced his three picks to the Federalist Society, whose selections were all preppies famous for their civility (except when they drink beer). The Court’s corrupt culture precedes Trump’s election and encompasses liberal justices.

“And since Trump plans to use the judicial system to carry out his political vendettas, his pick for attorney general will be no less important. Imagine former New York Mayor Rudy Giuliani or New Jersey Governor Chris Christie going after Hillary Clinton on orders from President Trump; quite aside from their approach to issues such as the Geneva Conventions, the use of police powers, criminal justice reforms, and other urgent concerns.”

Trump’s AGs were the pathetic Jeff Sessions and the standard-evil-Republican William Barr. They were bastards but they didn’t lock up Clinton or commit any war crimes that the US hadn’t committed before (I think Gessen was referencing Gitmo; otherwise we usually have the Department of Defense violate the Geneva Conventions, not DOJ).

“The power of the investigative press … will grow weaker. …

“Even in the unlikely event that some mainstream media outlets decide to declare themselves in opposition to the current government, or even simply to report its abuses and failings, the president will get to frame many issues.”

The Washington Post changed its motto to “Democracy Dies in Darkness,” tripled its digital subscribers by September 2017, printed books’ worth of leaks from the Trump admin, basically declared itself at war with the government, then blew all its newfound credibility on woke shit. In October 2023 WaPo announced it would lay off 240 people.

“It is no fun to be the only hysterical person in the room. Prepare yourself.”

Hysterics had plenty of camaraderie during the Trump years. 

“There will be more wars, abroad and at home.”

The war on vegetables?

“Don’t make compromises. In an autocracy, politics as the art of the possible is in fact utterly amoral.”

Gessen ends the piece by calling out Democrats’ past fecklessness (a fair point). The last lines: “That should not be normal. But resistance—stubborn, uncompromising, outraged—should be.”

The documentarian Michael Moore called for “resistance” the next day. His fellow blowhard Keith Olberman picked up the chant a few days later. 

The #Resistance might be credited to Gessen.

Best Year Ever

The day after Autocrat went up, Gessen appeared on Rachel Maddow. Maddow quoted the graf about Gessen having survived autocracy herself and called the essay “remarkable.” A few weeks later Chris Hayes had her on. He referred to her as a Russian journalist “who knows a thing or two about covering autocrats.” He addressed her: 

“Like you study American politics. You write about it. You’ve written the book on Putin.”

In the 12 months following the election, Gessen published at least 39 pieces of writing on Trump at various outlets including the NYT, New Yorker, and NYRB. She repeatedly drew on her knowledge of Russian politics. 

The reason you heard Trump compared to Putin so many times in 2017 is because Masha Gessen wrote a book about Putin.

Gessen was not a total hack during this period. She tamped down the wildest speculation about Trump colluding with Russia to steal the election, for example. But she was just one writer, with one drum to beat. Why did we hear so much from her?

Gessen hit the spot for libs. It wasn’t just her big bag of dictator fun facts and Hannah Arendt quotes. As a stern swarthy lesbian who never smiled or seemed to wear makeup, she served as a visual rebuke to the shimmery blonde princesses of Trump world — Dostoevsky staring down the ditzes.

That year Gessen joined the staff at the New Yorker and published a book about Russia’s slide into what she called totalitarianism, The Future Is History. It won the National Book Award. The famed political theorist Francis Fukuyama gave it a positive review in the NYT, though he politely noted: “One cannot really label Russia as totalitarian in the absence of a strongly mobilizing ideology.”

Extending the High

In December 2017, Gessen delivered a speech about her life at the New York Public Library. A version of it is posted at NYRB. It might be the first time she publicly referred to herself as transgender.

Gessen describes attending a dance for gay college students at age 15 and deciding “This is who I could be.” She says this was a “moment of choice” and dings gays who claim their sexual orientation is innate:

“The latter [view] was based on choicelessness. A choice may have to be defended—certainly, one has to be prepared to defend one’s right to make a choice—while arguing that you were born this way appeals to people’s sympathy or at least a sense of decency. It also serves to quell one’s own doubts and to foreclose future options.”

This provocation was not original. Attacking the (correct) idea that gays are “born this way” had become trendy several years prior.

It’s unclear from the speech whether Gessen is actually attracted to women, men, or both. She claimed in 2023 that she’s always been attracted to both. At the time of this writing, she has two ex-wives and a female fiance. 

As she’s describing her return to the US in 2013, Gessen applies the same condescension to trans people:

“[S]ome of the women I had known had become men. That’s not the way most transgender people phrase it; the default language is one of choicelessness: people say they have always been men or women and now their authentic selves are emerging. This is the same ‘born this way’ approach that the gay and lesbian movement had put to such good political use …”

She brings it back to herself:

“I found myself feeling resentful at hearing these stories [of friends’ transitions]. I too had always felt like a boy! It had taken some work for me to enjoy being a woman (whatever that means)—I’d succeeded, I had learned how to be one. But still: here I was, faced with the possibility that in the parallel life that my left-behind self was leading in the United States while I was in Russia, I would have transitioned. True gender (whatever that means) didn’t have much to do with it, but choice did.”

Sounds like an open-and-shut case of social contagion. Underneath the severe-intellectual persona she’s a trend-chaser who feels “resentful” when her friends get attention.

But Gessen views her transition story as one of “the choicefulness of life.”

Gessen had been taking (female) hormones ever since having her ovaries removed. In describing her decision to switch to a “low dose” of testosterone (steroids), she observes:

“I had some trouble with the evidence part of the science, because, as I have found, all published papers on the use of testosterone in people who start out as women fall into one of two categories: articles that aim to show that people taking testosterone will experience all of the masculinizing changes that they wish for, and ones that aim to show that women will have none of the masculinizing changes that they fear.”

If she noticed that the scientific literature was fishy, why did she risk taking testosterone?

After some Trump-bashing (he “appears to be obsessed with people who embody choice”), Gessen wraps:

“[M]aking choices and, more important, imagining other, better choices, will give us the best chance possible of coming out of the darkness better than we were when we went in. It’s a bit like emigrating that way: the choice to leave rarely feels free, but choices we make about inhabiting new landscapes (or changed bodies) demand an imagination.”

Lesbians Are Never Too Old for Peer Pressure

I can’t give you any stats on “grown up lesbians who say they’re not women.” The topic is un-researchable because there’s no such thing as lesbians who say they’re not women — only nonbinary queers whose identity must not be analyzed. So to suss out this phenomenon I’ll have to resort to anecdotes and celebrity gossip.

Friends keep telling me about lesbians in their peer group (not young) who’ve transed. Apparently the only person who doesn’t have a nonbinary lesbian friend is me, which makes sense — but I did have a middle-aged nonbinary lesbian opposing counsel. Some of these women medicalize, some don’t.

Elliot Page medicalized when she was well into her thirties, in 2020. Then her new girlfriend Mae Martin came out as NB and got a mastectomy. In Page’s 2023 memoir, she didn’t call herself a man but rather a boy or guy.

Beyond the lesbians who trans, there are many more who simply grandstand as trans allies. Gender-critical straights like to fantasize that lesbians are on their side because we shriek at the sight of male paraphiliacs on our dating apps. In reality, lesbian dating profiles are brimming with trans flags. It’s easy to swipe left on the gross guys and tell yourself “he’s just pretending to be trans.”

(BTW: the term “lesbian” is often used loosely to include women who identify as bi, as long as they’re not currently in a straight relationship. That’s how I apply it.)

Lesbians with a platform tend to go hard for trans foolery: Megan Rapinoe, Wanda Sykes, Hannah Gadsby, Judith Butler, Kara Swisher, Kristen Stewart, Randi Weingarten (head of the American Federation of Teachers), Cynthia Nixon, the governors Maura Healey (Mass.) and Tina Kotek (Ore.), Tegan and Sara (sob) …

In December 2023, NYT columnist Lydia Polgreen drew on her identity as a black lesbian to build a confusing defense of pediatric gender medicine. “I have never had much use for binaries. I was born to a Black African mother and a white American father …” 

Polgreen interviewed Gessen in 2023, at one point paraphrasing a gender philosopher. Transcript:

Polgreen: We all depend on the generosity of strangers to give us our gender every single day.

Gessen: That’s beautiful.

The queen bee of trans lesbians is Chase Strangio of the ACLU. Gessen wrote a tender profile of Strangio in the New Yorker in 2020.

Boihood

Gessen kept calling Trump names for the duration of his term. For example, in 2020 she explained to Irish media why “the word fascist is perfectly accurate when applied to Trump.” 

She continued:

“I have a lot of concerns about November, not least of which is that I'm not 100% certain that the election is going to happen on time.”

That year Gessen published a book of essays on Trump called Surviving Autocracy. They had titles like “A White Male Supremacist Presidency,” “Waiting for the Reichstag Fire,” and “Words Have Meaning, or They Ought To.”

The NYT’s Jennifer Szalai reviewed the book:

“As a gay parent, Gessen had confronted a Russian regime that threatened to remove children from same-sex families. When Gessen speaks about autocracy, you listen.”

In her New Yorker columns, Gessen covered her fellow resistance heroes Wesley Lowery, Ilhan Omar, and Greta Thunberg — twice (she also delivered a lecture about Thunberg at the Aspen Ideas Festival in 2019). She taught a class at Amherst and Bard called “Fact, Fiction and the Truth,” then landed on the faculty of CUNY's journalism school, which had awarded her an honorary doctorate. She scored press coverage for resigning from the board of PEN America on principle.

And she wrote about transgender rights.

“The Pull that Human Reproduction Has”

In 2020 the British High Court ruled that kids couldn’t consent to puberty blockers, in response to a petition brought by the female detransitioner Keira Bell. (The decision was later overturned.) Gessen covered it for the New Yorker.

In the piece, Gessen does not acknowledge that cross-sex synthetic hormones have side effects. She claims “the line between reversible and irreversible effects of hormone treatments isn’t as clear as their opponents seem to think[.]” She acknowledges the health risks of using puberty blockers for over a year – and suggests that kids therefore skip them and go straight to synthetic hormones. 

As for infertility:

“That one person’s testimony convinced the [British High Court] to make a decision that will affect untold thousands tells us more about the pull that human reproduction has on the imagination than it does about gender transition.”

Gessen has three kids, one of whom she carried and breastfed. From a 2023 interview transcript:

“We normalize regret in other areas of life. We do things and then we regret them. We have children and regret it. All the time. It’s perfectly normal. [Laughs.]”

Back to the Keira Bell essay. Here’s Gessen on whether blockers should be banned because they cause loss of sexual function:

“[T]his argument rests not only on a narrow definition of sexual pleasure but on an impossible ideal of comprehension: we can never fully imagine loss, especially the loss of something we’ve never had.”

How young is too young?

“None of us has ever been as innocent and ignorant as the children of our imagination, and none of us will ever be as wise and competent as the adults we make ourselves out to be. What if we saw ourselves as always changing, always uncertain, but always capable of making choices?”

The word “liberation” comes up. It seems likely Andrea Long Chu took inspiration from this 2021 piece for his 2024 New York Magazine cover story.

“I am unrecognizable, unintelligible”

Gessen has by now written several pieces on trans-identified kids. I think you’ve suffered enough. Let me just show you this from her 2023 interview:

“I remember getting on my bike in Manhattan, maybe four or five years ago, and suddenly realizing that this sense that I am unrecognizable, unintelligible to the world in which I live, was gone [because people understood trans-ness now]. I would bike down the Hudson River Greenway, and people would see a transgender, or gender-nonconforming, person, riding down the Hudson River Greenway. And maybe there would still be children tugging their parents’ sleeves and saying, Is that a man or a woman? But fewer. And the parent would probably be able to say, ‘Well, that’s probably a transgender person.’”

There are two types of people who enjoy living in New York City. The first type thinks, “it’s so exciting having 8 million neighbors I haven’t met yet.”

The second type thinks, “it’s so exciting having 8 million neighbors asking each other questions about my gender.” 

Watch Your Mouth

In 2019 Gessen covered a Supreme Court oral argument about trans employment discrimination. Justice Sonia Sotomayor, a liberal, asked one of the lawyers about women feeling uncomfortable sharing a bathroom with an MTF coworker. 

Gessen:

“I have no doubt that Sotomayor said this without malice—and without thinking that actual trans people were hearing her. But there was Chase Strangio, an A.C.L.U. attorney and transgender man … . There was Laverne Cox, a star of ‘Orange Is the New Black.’”

Sotomayor had caused harm.

In the 2023 interview, Gessen called out the liberal journalist Emily Bazelon. Her reporting nine months earlier on pediatric gender medicine had been “excellent,” Gessen said, except:

“[T]here’s a quote from Andrew Sullivan, the conservative gay journalist, who says, Well, maybe these people would’ve been gay—implying they’re really gay and not really transgender. That really clearly veers into the territory of saying ‘These people don’t exist. They’re not who they say they are.’ So that’s why it’s so painful. … I wouldn’t have [included it]. I think that piece would’ve been even better without that.”

Sotomayor and Bazelon almost certainly read the New Yorker, as do many other liberal journalists and judges. Gessen is trying to emotionally blackmail this class of people into self-censoring legitimate questions about trans. 

(A nuance Gessen missed: it’s likely Sotomayor disagreed with the bathroom-anxiety viewpoint, and was strategically lobbing it out there to let the lawyer shoot it down.)

In the 2023 interview, Gessen mocks people who disagree with her:

“Gender ideology is the specter of a totalitarian regime that will enforce gender fluidity.”

It’s a funny bit of projection since she’s the one who made a career out of calling people totalitarians. But now I can’t help but wonder: if Masha Gessen held hard power, what would she do to enforce gender fluidity?

Update 11/23/2024: Gessen has now compared Vice President-elect JD Vance to Vladimir Putin. “For more than a decade, Putin has made procreation a focus of his political rhetoric — much as JD Vance has in the last few years.”

This post was lightly edited after publication.