Jesse Singal and the Woes of Unchecked Hubris

He's singing his yesmen a powerful tune they can't resist, and his curiosity loses out in the process.

To have a mediation layer between a writer and their audience does have its advantages, but it’s one that early proponents of the blogosphere didn’t think was enough to warrant giving away what little power they had to media organizations–Jesse Singal was one such figure, and his writing well-after seven years at New York Magazine still comprises the hallmarks of a tentative, but mutually-beneficial relationship with an industry coming under increasingly-heavier fire for coddling his kind. It’s clear over the years that Singal places less faith in any semblance of viability at the very institutions he was once defiant of, and so it is on his Substack and a Patreon podcast he co-hosts that bets of future discursive relevance are currently being hedged.

Singal’s career is so wide-spanning that it’s impossible to glean a consistent theme across it, but one thing that remains constant is his penchant for ruffling the feathers of those he perceives as lesser-than actors in the media–in Singal’s imaginative, he is the Corey Robin of every opinion piece and everyone to his contrary is but a mere intern with no idea on how to work the cogs of journalism, be it investigative or opinion-based. Recent Vox defector Matthew Yglesias expressed a similar sentiment, though he chalked it up more to generational differences and the not-so-subtle insinuation that those who write with conviction are doing activism rather than journalism (as if though the two are somehow mutually exclusive).

The problem with both perceptions however is they posit an innate superiority to one’s craft that exudes a hubris so pronounced, it almost calls for doubt on their ability to self-reflect–it is true that many have been into journalism for shorter than senior bloggers and journalists can realistically fathom, but sheer experience doesn’t signify much given that bloggers themselves forewent the price of admission to media outlets because of arbitrary—often poorly-qualifiable—requirements of writing history. The goal with blogging in the first place was to start fresh with a page, let the pen do its thing, then put forth the result before outside judgement in the hopes of spurring improvement and growth–if Singal continues to fancy himself an innovator while refusing to entertain any challenges made by others on his claims… then he’s lost all impetus to self-improve, suggesting he considers his craft already free-of-flaw.

It’s a trap a lot of bloggers fall into once they’re a few years into their trade–they became complacent, or worse yet, they’re compelled to see any criticism as an attempt to exert outer editorial influence rather than enrich and add to what are often complex and nuanced conversations. With an editor behind, there’s the added pressure to meet a certain standard and not disappoint–but as readers become the primary audience you’re catering to, the addiction to a positive response loop starts to triumph above all. It’s something I—as a blogger for four years, and even longer if defunct attempts count—have to take conscious stock of, but Singal doesn’t seem so bothered by it.

This leads into what has become a primary contention with his writing from progressive intelligentsia–the almost-obsessive degree to which Singal’s public identity seems to be synonymous with anti-trans concern-trolling. It first rose to the forefront of media discourse when Singal wrote the cover story for the Atlantic’s July/August 2018 issue, regurgitating what has become a regular slant of attacks on trans people’s right to healthcare under the pretense of caring for children–though Singal would like to portray himself firmly as a liberal, his views are not dissimilar from what a conservative blogger like Andrew Sullivan would write on these issues. “Singal’s lamentations elicit a very particular weariness among trans readers. His logic is circular, and obsessive. In returning to the subject repeatedly, Singal seems intent on cracking some truth about the trans experience that is not accessible to him, as if provoked by that very inaccessibility. And this is the epistemological challenge that trans culture lays at cis culture’s doorstep: You must trust me to know my own identity. To extend full humanity to trans citizens means marking the limits of cis knowledge,” writes Jo Livingstone for the New Republic. “One of the reasons that trans skeptics get so riled by this demand is that it implies that their empathy and their intellect have borders. It also denies the universality of human experience, and undermines the notion of a pure discourse where only reason prevails. Ironically, nothing makes those borders starker than the Singals of this world patrolling the edges of a culture war, demanding that their opponents meet them at the fence for a healthy conversation.”

Those in the blogging class unfortunately lay cover to their worst offenders under the guise of professional courtesy, but Singal isn’t going to get that from me–he’s intentionally using his position as a prolific writer to alter public perception of trans people—perhaps even consequently public policy—and that shouldn’t stand no matter where you fall on the political spectrum. To even espouse being liberal while policing what trans people do with their bodies should be a first-rate violation of liberalism’s very own principles–from my own perspective though, as a socialist, trans issues cannot be holistically addressed unless there is true equality—material and otherwise—between them and their cis counterparts, and tamping down on their ability to access services crucial to their well-being and happiness runs counter to that principle, which makes it all-the-easier to make a solid case for.

It’s hard to tell whether Singal would ever entertain reading this story–after all, his reactions to past critiques seemed predictably-tepid. But it’s an important reminder nonetheless that with inking stories—on our own pages or those of the media—comes also great responsibility on top. For most, this means unconditional surrender to the whims of regular readers, not daring to break outside of familiar surroundings–for myself however, much about growing as a writer cannot be severed from my ability to look at the facts without some weird ideological hang-ups standing in the way of the fundamental work of critical inquiry.

Sure, the camaraderie I’ve oft-displayed towards my trans brethren bears its weight on the implied comparison, but at least its ideal outcomes aren’t informed by contempt–they’re collaborative in nature like the very project of liberal democracy is, and it’s why Singal would be remiss to deny his approach to trans issues is less conducive to good outcomes than he’d like to otherwise believe. If he wants his words to command more heed, he has to first listen before he speaks–it’s a rare quality for a blogger, but it’s one he ultimately needs to learn if he wishes for his reputation to no longer be synonymous with utmost intellectual dishonesty.