Utility Infielder

Jay Caspian Kang initially declined this interview. 

Anyone familiar with the 44-year-old’s oeuvre might be surprised by his reluctance to engage. Over a career that spans the last decade and a half, Kang’s survived (and thrived) in an ever-shifting media environment, carving out a wide purview with his ability and willingness to expound upon virtually everything under the sun.

As a writer and editor for the short-lived but influential publication Grantland, he and his cohorts pioneered a unique territory, treating nearly every subject—pop culture, internet trends, sports, really anything previously deemed superfluous by major publications—as not just worthy of spilled ink, but as a potential window through which to more clearly view the cultural zeitgeist. As a journalist, he’s written meaty long-form profiles and investigative pieces about a wide range of subjects, including affirmative action, online gambling, the bro-y media conglomerate Barstool Sports, and the emergence of the Black Lives Matter movement. He’s binge-watched North Korean television and embedded with anti-fascist groups for Vice TV. 

Even in an increasingly stratified editorial ecosystem, at his recent posts—first for the opinion section of the New York Times and now for the New Yorker—Kang’s added breadth, depth, and heft to two of the most influential desks in media. As a columnist, his range has yet to find the guardrails. He’s a polymath of the highest order. And his personal experiences—as, say, a poker addict, a backpack-rap connoisseur, and especially as an Asian-American millennial born to Korean immigrants—no doubt lend potent perspective to the mix of curiosity, observation, and analysis that earned Kang a Pulitzer nomination for commentary in 2024.  

Kang’s a surfer, too. His 2012 novel, The Dead Do Not Improve, is a madcap San Francisco–based noir filled with Easter eggs for the savvy surf-culture enthusiast. One of the book’s characters is a surfing detective named Sid Finch, who earns the nickname “Keanu,” scraps with naive interlopers in the Sloat Street parking lot, and delivers a polemic about the deleterious effects of surf cams. The novel also includes astute observations about surfing’s place in America’s cultural milieu. 

“Everyone here, they’re all fundamentally happy people who need this to temporarily displace their happiness, so they can discover it again,” another of the book’s characters, a pragmatic pornographer named Miles Hofspaur, tells detective Finch as they sit in a high-priced vegan café, before rattling off a list of things that rich people do: crossword puzzles and art galleries, volunteer work and “fucking opera,” John Updike and surfing. “It’s all the same,” Hofspaur says. “Bullshit engineered to make people bored and kinda miserable until they finish, at which point they can allow themselves to feel satisfied for walking the straight line.”

So it was surprising that, when I reached out to Kang, he told me he was hesitant to talk about surfing. Nevertheless, I persisted. And it turned out the reason for his initial reluctance lent itself to a discussion about whether ability or expertise in any subject is a prerequisite to writing about it.

Utility Infielder

MBS You’ve written a lot about cultural identity. Is there anything unique about surf culture that you’ve picked up on? 

JCK I think it’s interesting that there’s a division between the type of surf culture you’d see from, like, this Morning of the Earth, “let’s go camping” thing, or images of a dude shaping a board in the wilderness. And then there’s a different kind of culture that predominates down where my cousin lives in Huntington Beach. Why is there one kind of surf culture in San Francisco but a totally different thing happening down the road in Santa Cruz? The regional developments of it have always been interesting to me.

MBS You were ambivalent about doing this interview. Can you share why?

JCK I felt like I was not good enough at surfing to be featured in this [magazine]. I just got back from visiting my sister in Honolulu. And, you know, summertime, South Shore. Sometimes it’s great. Sometimes it’s 1 to 3 feet. And I was just struggling in 1 to 3 feet. I stepped on a sea urchin. I did everything that every kook does in Honolulu. I had this realization that maybe I’ve reached a certain point where I’m not going to get any better than this. I was never a good surfer. But I would call myself competent. I was just thinking, if someone sees this [interview] and then sees me in the lineup, I’m going to be embarrassed. 

MBS I get that. But you write about such a broad range of topics. And I think writing requires a certain amount of courage to think you can become or pretend to be a kind of expert in something. Elite skill at something, though, does not seem like a prerequisite for writing, analyzing, or talking about that something in an informed way. Why is surfing different?

JCK It’s because it’s so hard, and the people who are good at it are so good. Maybe I think they must have some special knowledge that I don’t. And so maybe I should just shut up about it, right? Every time I’ve written about it, I’ve been quite clear that I am not good at surfing, but that it bestows some sort of spiritual peace upon me. I do believe that the first time I caught a wave was one of the best moments of my life. I get very emotional thinking about it. And, yes, I do try to chase that. Why is this so appealing to somebody that is so bad at it? Why have I centered so much of my life around it? What is the value of chasing something that you know intellectually you can’t attain? Those are the sorts of things that have compelled me to write about surfing when I have.  

MBS You once wrote that you got into surfing when you were struggling with your first novel. Like it was a kind of avoidance. 

JCK This is almost 20 years ago. I went with my friend down to Linda Mar and rented a 10-foot soft top, as one does. At a certain point, I finally caught a wave that was not white water, and that was quite thrilling to me. I was a high school teacher, and my schedule at the time was not so intensive, and the school I taught at was quite close to the beach. I bought a 9-foot longboard and just took it everywhere I went. Before long, I was going almost every single day. I just got very addicted to it. I think, because I was struggling at the time with this book, and I didn’t have any kind of writing career to speak of, there was some way in which surfing was filling time but also giving me some sense of an alternate life outside of all this stuff I had put in my head about needing to become a successful writer. The disappointments of that were massive at the time. I couldn’t even get emails back. I was rejected by every agency in New York City. This is obviously the mythology of surfing, and maybe the most cliché thing ever, but I just thought, “What if my entire life could just be this?”

MBS In your review of William Finnegan’s Barbarian Days for the New York Times, you wrote, “I concluded that writing about surfing was impossible because surfing elicited happiness, and it is impossible to write about happiness.” Have you thought more about that in recent years?

JCK When people do it in an earnest way, I think they have to fully commit to it or it falls apart. I have a friend, Jaimal Yogis. He wrote the book Saltwater Buddha. Jaimal is a really earnest guy and a really good surfer. He can write about surfing in that “this is what surfing means to me” way and doesn’t try to hide behind any irony or anything. That’s not something that I feel comfortable doing. It’s not that I don’t feel that way. In fact, I feel that way maybe as intensely as Jaimal does. Part of it is that I’m just not as good of a surfer as him. The other part is that there’s just something in my brain that won’t allow me to access that. It’s not a positive trait. That’s kind of my own failure in writing, I think. 

MBS Recently, for the New Yorker, you used overcrowding and an increasingly concerning lack of etiquette at your home break as a way to point out that it’s impossible to overcome the onslaught of information and misinformation online. In your view, what’s happening with surfing content on, say, Instagram? 

JCK The central argument I was making, which I think you paraphrased quite well, was that the internet has changed everything. There’s two things. In terms of surfing, obviously Surfline has changed everything. There’s a color and a rating, and everybody just follows that. It has completely changed the way in which crowds operate. The other thing, because so much of Instagram—and surf content on Instagram—is engagement based, the stuff that does well, or gets the most engagement, is videos of people fighting or people arguing over whether somebody burned somebody or not. I think at places where there’s a lot of new people surfing and their introduction to surfing has been through Instagram, they mimic that kind of behavior. 

MBS In that piece, you reference Neil Postman’s famous book Amusing Ourselves to Death, which, as you noted, was a polemic against television. As someone who writes about tech and media, how do you see it? Social media: generally bad for us? Or bad, but so is TV?

JCK I think social media is much worse than television. I think television was generally bad for our generation’s erudite knowledge and ability to interact with the world. But it was not alienating, because we all watched the same shows, right? Social media is so optimized to the individual. At some point, if you spend enough time on it, you become what it is they think you are. That creates pretty intense alienation. The things you’re experiencing are so much different from the next person. 

MBS Earlier in your career, you were at Grantland, Bill Simmons’ short-lived sports and culture publication. Looking at the media landscape today, Grantland’s influence seems underrated. How do you view that publication’s prevailing influence? 

JCK I think—this is kind of boring—but, aside from a couple of us, the people who wrote for Grantland had never had a writing job before. Including me. Most of us were people that Bill found on the internet, writing blogs for our own entertainment. I think what Bill did was that he gave us all jobs and then professionalized that kind of writing. After that, a lot of those people started to think that maybe there’s some kind of career in doing this kind of writing. There are negatives to that, like the fact that maybe some of that kind of writing now can feel derivative. But the positives far outweigh the negatives. Writers deserve to have stable lives, you know? Secondly, the kind of stylistic part of it is not something that I thought much of at the time. When I was working as a writer and editor there, and we were part of ESPN, I don’t think I thought what we were doing was all that different than what ESPN was publishing. But something about Grantland made it feel like a home for readers that was different, and people got attached to it in a way they wouldn’t have with ESPN. It’s interesting because I’ve now worked at basically all the media companies. Maybe 75 percent of the people who come up to talk to me about writing want to talk about Grantland. 

MBS You’ve written fiction, worked on documentary projects, long-form magazine features. You’re a columnist. Where do you feel you shred hardest?  

JCK I like doing columns because they come out, some of them are bad, and then they’re over. Sometimes you write something and you’re like, “Man, I didn’t really come to any point in that one.” But it comes out and all you can do is say, “Okay, next one’s going to be better.” You hope that your total batting average is high. With fiction, it feels like your soul is on the line. If a sentence is bad, then you suck as a human. 

MBS How does surfing fit into your life nowadays?

JCK If I can go once a week, it’s great. I’ve got a buddy here in Berkeley. We’re about the same age and both busy. We leave at 9:30 a.m. and can generally get across the bridge without traffic. We surf and then we go get lunch at one of the same two spots. And then we drive back. It’s the best day of my week, always.