The Hater With A Heart of Gold
Writer and Critic Jay Caspian Kang Has Some Questions About Your Questions
- Text: Haley Mlotek

Jay Caspian Kang will be the first to tell you what he doesn’t like. As a writer, his essays refuse easy categorization; as an editor, his work rejects easy compromise. As a person on Twitter, he is quick to press send. Like the minutes on an endless clock, those tweets might auto-delete and disappear, but their impressions remain. In September he became the subject of a contentious Twitter discussion about how profiles should or shouldn’t be. Lines were drawn, group chats lit up, and surreptitious subtweets multiplied as day turned to night. Meanwhile, the long-neglected item on my to-do list reminding me I still had to email Kang to set up this interview was mocking me. Yikes, I thought, this is going to be awkward.
“The irony did occur to me,” Kang admitted when we spoke over Zoom a few weeks later, about him agreeing to a profile so soon after publicly criticizing the form. “I guess you grow up thinking about what type of writer you’re going to be, and for me, that was people who could make their subjects very uncomfortable.”
Well, clearly neither of us are very concerned with comfort, or we wouldn’t have become freelance writers. We work in a strange industry. Our words are trapped behind liquid crystal, bought and sold for pennies. It sounds like a fairy tale, except that the reality remains so ordinary. For example: the first time Kang and I talked, it was about helping freelancers find better healthcare options.
Just over ten years ago, Kang published “The High Is Always The Pain And The Pain Is Always The High,” an essay about his gambling addiction. “I couldn’t get it published for five years,” he told me. “And then it got published by The Morning News for $50. When I read it today, I’m like, this is better than what I can write now.”
Kang’s style of observation is often like this: high standards and blunt assessments. I’ve read Kang’s writing for many years and would respectfully disagree that his best writing is behind him. At the same time, I must admit that even a backwards glance shows an incredible collection: The author of The Dead Do Not Improve, an almost-noir novel, he was a frequent contributor to much-loved and now-defunct sites like The Awl and Grantland, an editor for The New Yorker, a producer for Vice News, and briefly—because he might be principled but he’s no stoic—making branded content for Wieden+Kennedy. He’s written about the complex infrastructure and chaotic fandoms of sites like Barstool, the collective bargaining agreements at the NBA, the heavily weighted significance of Jeremy Lin’s career, the protests at Standing Rock and, this past summer, all over the country. He’s bracketed the greatest divas of our time, and was one of the first people to bravely say that the musical Hamilton is bad, actually.
At his current position as a contributing writer for The New York Times Magazine, his work sacrifices nothing for the sake of simplicity. In 2015, he profiled Johnetta Elzie and DeRay McKesson as core organizers within the complex collective effort that was the Black Lives Matter protests in Ferguson; his 2017 essay about Michael Deng, the college freshman killed during a hazing ritual at an Asian-American fraternity, was a reckoning with the brutal cycle of alienation and violence among young men. His upcoming book, The Loneliest Americans, will continue to explore these themes of identity and community, race and class, reporting and recounting what it means to tell the story as it happened.
Kang’s writing has a sense of his own presence: how his perspective ultimately shapes our reading of the topic. It has, as well, a feeling for the present: the time and labor is as important to him as the finished product. At one point, I asked him when he knows it’s time to stop researching and start writing. He told me that he begins as soon as he can—that he enjoys the work of writing so much he can’t wait to start. As readers, we can tell.
Haley Mlotek
Jay Caspian Kang
Do you think you’re going to like this interview?
Probably not. My general rule is: you shouldn’t talk to reporters ever. And I try to live by that rule myself, but, I don’t know…I think I’ve lived through some things in my career that could be helpful. Even if I do like it, I’ll have to pretend to hate it.
Whatever you have to do on Twitter, I’ll understand. I do think of you as someone in search of a fair fight. Does that seem accurate?
I think there’s definitely a place for profiles that are more of a mutual celebration between writer and subject, and there are people who do that well. I just wouldn’t want to write like that. I have a much more adversarial relationship with pop culture in general.
We should care about celebrities. We shouldn’t deify them. If they’re great people, then perhaps we should say so, but when people are great that’s boring. There should be some sort of examination of their work or of them; you should say something that they wouldn’t say themselves.
What does it mean to have an adversarial relationship to pop culture?
I’m a huge hypocrite on this. I don’t really watch television or movies—part of this is being the parent of a young child—but I watch a lot of sports, which has the same problems—we deify athletes, and turn them into political figures when perhaps they’re not.
I do think, right now, we try to have conversations about race and gender and power, and we use celebrity and pop culture as a lens. There’s too much putting critical theory onto pop culture. Parts of the media glom onto stories that create mirages. I don’t want to sound like some sort of boring Marxist, but it doesn’t address the material conditions that created this problem.
There’s too much putting critical theory onto pop culture. Parts of the media glom onto stories that create mirages.
You can be as Marxist as you like. You’ve written about this contradiction before—in a New York Review of Books essay, you wrote that when LeBron James wears a “I Can’t Breathe” t-shirt, it creates a meta-conversation about an athlete’s responsibility to a political ethos, rather than the idea itself. You said it doesn’t push the idea forward. Is there ever a time when pop culture can push an idea forward?
I don’t think trying to examine the role of the artist or the athlete or the pop star matters. What swung people’s opinions about the protests in Minneapolis? It wasn’t Lebron James or the NFL. It wasn’t the fact that every corporation did a tweet. It was the videos of people getting brutalized by the police.
I think these athletes care deeply. I also think they’re very young, and they’re being asked to lead a movement. They have influence, and some of them seem to understand that: they’re going to protests, they seem willing to stop playing. I don’t think the older guys understand it—they’re used to making thirty million dollars a year. They’re much richer and more powerful.
Well, there’s the Marxist part again. That’s class solidarity. I do agree with you, and I share a lot of these opinions about the way we fixate on celebrities, but at the same time…I think about what it felt like on the night of the NBA work stoppage. This was after years of people organizing, protesting, and then here was a group with enormous amounts of power flexing it for the same cause. There was an emotional aspect to that action that made me reconsider the intellectual approach. A feeling that more was possible piercing the strange, surreal bubble of this basketball season.
Oh, for sure. I was moved that night. They did something that professional athletes have never done before. There have been other work stoppages in the league before, but that was like, a pre-season game, or Kareem Abdul-Jabbar at the Olympics. It’s probably the most significant thing they’ve done, and it was the act of abandoning what they had been told about their “platforms,” why pairing Nikes with slogans could somehow be meaningful to kids. And they said no. Or at least some of them did.
I think what mattered was that what they were asking for was not tied to being wealthy and famous. That night, they had the power to reject that. That was the distinction, at least in my head.
In your own work, do you see a distinction between forms and styles? Much of your writing could be considered personal essays, and I was wondering if you thought of yourself as a memoirist.
I don’t have much self-awareness about my own writing, and so I don’t have a theory about it. But I do tend to write about myself. I put in my opinions, and I try to think of anecdotes that might be relevant. Part of that is because the journalists I like reading did that. Obviously everyone likes Joan Didion, but I really love Joan Didion. For me, it’s her profile on John Wayne, how she would sit in his hut in Colorado and listen to the wind whipping through the grass.
For young people who are trying to become journalists, maybe reading Joan Didion is not the best idea. It takes up so much space in your head. I wasn’t trained as a journalist, and I always thought I’d be a fiction writer. All of my references for that type of work was like, maybe I’ll read Denis Johnson’s journalism, and it’s just him getting fucked up somewhere.
I find that some of the ways in which journalists avoid inserting themselves is a little unnatural. I didn’t want to construct sentences in a way where I was consciously taking myself out. I want to read somebody with a real point of view, so I try to write that way too. I tend to write about the thing I find myself having an emotional reaction to, a personal resonance. It makes it so I have to be more objective, because I would be embarrassed to write something that was effusive.
Obviously everyone likes Joan Didion, but I really love Joan Didion
In the same way that your writing could be called personal, do you think you would ever call yourself a political writer?
No, I think I write more about race than politics. To me, the two are the same, but when I hear the term “political writer” I think of people who cover campaigns. But I guess if you mean: do I try to make some sort of larger political argument in the work that I do? Yeah, I try. I would like the reader to come away with something where they’re thinking about more than just the actual subject. I think everyone tries to do that; I don’t think I’m alone there.
You mentioned that you’ve learned some things that could be useful for younger generations.
I think there’s a little bit too much of people who think of writing as a career. And they don’t think of it as something that you do as an art, or whatever you want to call it, in a cheesy way. It is inherently cheesy to think about it like that, because you’re like, well, I’m not painting some masterpiece. But for me it was important to enjoy what I was writing and to enjoy the process of writing.
Let me start over. I do think young people should have a day job. If you’re young and you don’t quite know what to do yet, and there’s no real money or any sort of clout, you’ll find the things you actually like. But you shouldn’t pigeonhole yourself into taking writing jobs that you hate, because you’ll end up hating writing.
“The High Is Always The Pain And The Pain Is Always The High” was unencumbered. It was cathartic. I think if you have none of that feeling in your writing, nothing precious at all, it’s very hard to keep doing it. You grow to hate it. I don’t think writers should hate the process of writing.
I often say that writers should find a way to take care of their material needs so that they can protect their real work. My own experience was very influenced by a specific moment—part of a certain era of women’s digital media—in which writers were pushed to share some of their very worst experiences for $50 and a byline. I have two competing impulses here: I worry about writers being exploited. I also know it’s true that sometimes the worst thing that happened to you is what you need to write about most.
It’s a fine line. Once every two or three years or something people have the same conversation about personal essays, and I just get a little frustrated, because it’s like, well, those are by bad writers. If the question is whether there are too many bad personal essays out there, I don’t even think that’s true. I think there’s much more bad journalism.
Again, perhaps this is me being a little precious, but I like reading them, even if they’re poorly written. I used to read LiveJournal a lot, and I loved that whole meta-conversation of: I know this is so boring, but…
The second part of it that bothers is me is that it seems like having lived some sort of interesting life is attached to having some sort of status. I don’t understand why we debase one form of writing when it’s produced so much of the best work. “Notes of a Native Son” by James Baldwin is probably the best essay in the history of America, and that’s a personal essay about his father, about the Harlem riots, about feeling so angry. It’s strange to think that the works that people feel the most passionate about are often personal essays and yet, for some reason, they are also derided.
I do find that when people come to the defense of essayists, I hear a sort of reification of the same hierarchies: this matters because it’s actually good, this deserves respect because the form itself is good. And then what’s not considered classically or traditionally good becomes a debate about whether it should even exist.
Yes. I think it’s very easy to gatekeep when the work itself is an expression of self. And the response is well, we don’t want people like you in here talking about yourself.
You’ve written, too, about being in newsrooms where it’s painfully obvious that they don’t have the writers or editors they need to cover the moment. You’re technically a freelancer now, so not part of a newsroom in the same way, but have you observed any changes since then?
I do think there have been changes. I think some of those prestige institutions have made a real effort to bring people of color into their newsrooms. And I don’t think we should be so cynical to think that that doesn’t matter, because it matters to the people who are doing those jobs.
I felt very isolated at The New Yorker. I don’t think it really affected me in a deep way, but it wasn’t pleasant. It sucked. And it matters to the people who work there to see other people like them, so they don’t feel so isolated.
If you bring somebody who hasn’t spent their entire lives around elite white people, then there’s other challenges. I think they should diversify these places both by race and class.
But at the same time, I don’t know if I truly believe that having a diverse set of people write for elite institutions will change much in terms of the way the public thinks.
I think these institutions should change, and I hope that people find ways to get fairly paid in those institutions, but I’m not sure if the diversification of media is the most important cause. I guess it’s inspiring when people withhold their labor, but I don’t feel particularly moved by the media doing it. That doesn’t mean that they shouldn’t, just that it’s not on the same scale. Sometimes I feel like the same eight people are talking about the same eight jobs, and the same eight people have been up for those same eight jobs for twenty years, and that we derive great political meaning out of small shufflings. Does that make sense?
If you bring somebody who hasn’t spent their entire lives around elite white people, then there’s other challenges. I think they should diversify these places both by race and class.
Yes, definitely. It’s true that it’s proportional. At the same time, I do think a lot of the work of media is supposed to be in service to a much better world than itself. I wonder what a sustainable industry could look like, let alone an equitable one.
Oh yeah, I have no idea. It’s one of those questions—what would the newsroom look like?—and I don’t think anyone has a good answer to that. We just know it’s not this one.
Yes. We’re very sure about that. So are you a Marxist?
I don’t know. I would say that what happened for me was that I always had these ideas before, and it’s relatively recent for me to identify myself as being on the left. I’m trying to figure out what the actual solutions are. I would say that what happened was that I always had these ideas, and I think that I’ve had a reawakening.
And what do you think is the most important cause?
A way to get the energy of the millions of people who came out for the protests, and to sustain it in a way that will lead to solidarity. You have these moments where people just wake up, and they realize that their struggles are the same—I think working towards that is the most important thing.
Haley Mlotek is a senior editor at SSENSE and an organizer for The Freelance Solidarity Project, a distinct division of digital media workers within the National Writers Union. She is currently working on a book about romance and divorce.
- Text: Haley Mlotek
- Date: December 23rd, 2020