We talked by phone this week with Jay Caspian Kang, author of The Morning News essay “The High Is Always the Pain, and the Pain Is Always the High,” our latest Notable Narrative. Kang, who has written for deadspin and theAtlantic.com, has also created the Kang Diva System, a mathematical method of ranking female singers within specific genres (a system whose conclusions we do not necessarily support). Here are excerpts from our conversation, in which Kang talks about his commitment to a loser’s narrative, the daily writing drill his mother made him do for nearly a decade, and his conviction that there’s “no worse way to make several thousand dollars than playing poker all the time.”

Had you written about your gambling addiction before you did this piece?

The piece was written a couple of years ago, and I think it was the first time that I really wrote about gambling. I moved back to New York, and I had enough time to reflect on what had happened, because while I was doing it, I didn’t really process it. It took a little while for me to be able to figure out what had happened.

How long have you been gambling, and how long have you been writing?

I’ve been writing since I was a kid, I guess. My mom used to make me write a page about what had happened in my day from when I was 5 years old until I was about 14. She really was a taskmaster. But for some reason, even having to do that, I didn’t hate it. I did it all through high school and college, and then I went to get an MFA.

As far as the gambling question: I started when I was in New York around 2003. I played poker pretty consistently for about five years. And then it really tapered off, and I don’t play at all anymore.

What made you realize you wanted to write about your gambling life?

It was sort of cathartic more than anything. I needed to process it in a way.

There are two things, really. The first is that people don’t write about the ugly side of gambling. Playing some of these bigger games, I would occasionally see some of the people who were on TV, especially in Vegas. I would sit down at a table, and I would recognize people who are cast as these genius MIT grads who had come to Las Vegas and were now millionaires. And there’s no distinguishing them from anyone else, except that they had been on television. They’re just as miserable as everyone else. I thought somebody should write something other than just success stories.

There’s this idea of the redefinition of Vegas that started maybe in 1998, where it went from being this seedy, depressing place to being this land of opportunity. I had sat around enough poker tables to realize that none of the people you play with are really happy about it, especially these guys who have been playing for a long period of time. There are all these younger kids or people who just started where the thrill is still there, and they play very disciplined, and it’s not a degenerate activity. But you watch those guys – as happened with me – you see them slowly deteriorate into bad habits, and they start to look a little bit different. By year two or three or four, you can see that if they somehow could stop, they probably would.

There’s no worse way to make several thousand dollars than playing poker all the time. The money stops meaning anything after a while. At the beginning, I remember, it was about the money, because I had no money. I was a graduate student. I ate rice and beans every day from the Dominican place across the street, and I couldn’t even afford the chicken to go with it.

And then I scraped together enough money, and I won like the first 15 times I played. I made a ton of money. I bought an iPod, and I went out to dinner. I could go out for drinks with my friends. At the beginning it was nice to have that money, but very quickly it became about winning and losing – and mostly losing, because even when I was winning consistently, I didn’t remember winning.

All you remember, really, is losing – especially if you are a disciplined player and you’re playing the odds correctly – when the odds just don’t work out. Even if you have a 68 percent chance of winning a hand, 32 percent of the time you’re going to lose. Those are the things that everybody talks about and remembers. That’s all people ever talk about around the poker table, the time they were a 5-1 favorite and some idiot pushed all in, and they lost everything. The conversations are all about losing.

If you wrote this two years ago, how did it find its way to where people could actually read it?

I wasn’t really aware of The Morning News, and then a friend sent me an essay by Anthony Doerr. He knew about him because he went to Bowdoin many, many years before my friend and I did. I started reading the content on their site, and I always liked it. I have this essay that I wrote, and it was just sitting on my hard drive. I thought they might be interested, and so I submitted it.

When we think of narrative nonfiction, there’s the idea that real-life stories can be crafted to be like fiction. But at one point in your essay, you’re looking at the framework of story, this narrative of loss and losing coming down around you, as a sort of prison. I thought it was an interesting interweaving of this idea of storytelling and an individual life.

I think that’s actually very accurate. What I wanted to get across was that the reason why so many people become problem gamblers is because the idea that you can make a fortune and lose a fortune in a single day – or the idea that you can have such disastrously bad luck, or fortune-building good luck, and it all just happens one hand after the other. You can win enough money that somebody would work a whole year to earn in a period of 8 seconds, or you can lose everything that you have so quickly.

There’s nothing that really compares to that in terms of swings of fortune and ruin, and that takes over your life. There’s no other story that’s as good or as high-stakes as when you win or lose everything that you have at a card game. You start to become numb to everything else that’s happening in your life. I had a job – I was teaching history at a school. The amount of money I was making teaching history at school was nothing compared to the amount I was winning and losing at playing cards. My job became meaningless. Ultimately, the relationship I was in that time became kind of meaningless, too, because it didn’t compare to the fast life that playing cards seemed to offer, which I never really accessed so much, but I saw it.

There’s a sense of your writing self – this earnest guy writing a book about an earnest protagonist – and your gambling self being slowly squeezed together across the span of the essay, until they merge. Have you written more on gambling since?

If I were going to do anything longer, it would have to be along the same theme of losing. That was what I wanted to talk about – how losing creates a narrative and how you follow that very faithfully, even when you don’t think you are. You are trying to lose, so that you sort of feel the spike of whatever horrible emotion you feel when you lose.

Everybody says the same thing. If you talk to somebody and they’re playing a pretty small game, and all they’d win is $100, the joke is always that it’s better to lose $500 than win $100. What did you spend all your time there for if all you’re doing to do is win $100? That’s not explained in any gambling book, and that was my main objective.

I didn’t win or lose enough money to have a really compelling story. I just read one that was really good by this guy named Josh Axelrad, who lost $700,000 playing online poker in a very small amount of time. I don’t have stories about playing poker with NBA stars or anything like that. My poker life was pretty seedy and not so great, but at the same time, it wasn’t so seedy that it would make its own interesting narrative. Yes, I played in underground clubs in New York City, but the guys I played with were kids from Westchester or Columbia philosophy Ph.D. students. It wasn’t like the movie “Rounders,” where everybody was some sort of great archetype of New York underground society that might or might not really exist.

What are you doing now?

I just finished a novel, and I live in San Francisco. I spend most of my time writing, and I go surfing a lot. That’s sort of replaced a lot of what gambling offered, because I’m not particularly good at surfing. Most of the time when you go surfing, especially up here around San Francisco, it’s pretty brutal, so you spend a lot of time either trying to paddle in place or getting beaten up by waves. It’s kind of constant punishment, which is something I might need in my life, and surfing is a much healthier and nice way to have that happen. I don’t want to make some grand metaphor about it, though.

Anything you want to say about the structure? You seem to have divided it into pretty discrete sections.

I wanted the sections where I’m actually discussing professional poker players to be distinct, because I wanted the idea that these people have the same issues as every other problem gambler, but they exist on a higher stage and play for higher stakes. And so I wanted that narrative to be a little bit separate, because I wanted readers to draw their own conclusions about those people. I did want the whole structure of the story itself, of my story, to be circular but also embedded in the stories of the higher stakes players.

The guy who edited it at The Morning News, Rosecrans Baldwin, did a good job. The original version was something like 7,500 words, and we ended up chopping off a good 1,800 words, which were mostly about a Dostoevsky novel called “The Gambler,” which he wrote to pay off his gambling debts. It was more of an erudite discussion of gambling book history, which in the end, I don’t think was necessary.

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For more on this Notable Narrative, see our commentary on Jay Kang’s essay.

Image of Jay Kang by Eric Wolfinger.

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