WHEN PEOPLE ROMANTICIZE literary New York, the conversation inevitability turns to famous writers and the places where they drank: Dylan Thomas at the White Horse, Faulkner and Hemingway at the now defunct Chumley’s in West Village, the elegant drunks at George Plimpton’s apartment. Nowadays many literary functions in New York consist of some hummus and maybe a glass or two of white wine and everyone’s home in time to catch The Daily Show. Multiple factors have contributed to this taming of New York letters. Many working writers are sequestered to academia, maybe due to the fact that New York has become prohibitively costly for artists to live as artists. New York Tyrant and Tyrant Books, a literary magazine and small press, is the exception to the rule. When I sat down with Giancarlo DiTrapano, the editor of Tyrant Books, in the little studio apartment which doubles as the Tyrant’s offices for this interview, he offered me Xanax, whiskey, and cocaine (not kidding) on a silver platter.

Founded by Giancarlo in 2006, New York Tyrant’s roll call of published authors reads like a who’s who of the 21st century’s best writers: Brian Evenson, Noy Holland, Michael Kimball, Gary Lutz, Rachel B. Glaser, Scott McClanahan, Sam Lipsyte, Padgett Powell, Breece D’J Pancake and Gordon Lish, to name a few. Tyrant consistently publishes writers that large houses refuse to touch — and it’s growing.

Giancarlo, Tyrant’s editor, publisher and publicity director, lives in Hell’s Kitchen, not far from the big publisher’s corporate offices. When you come up from the subway on 42nd Street you’re bombarded by grinning idiots enjoying Giuliani’s Disneyfied New York. But walk a few blocks to Giancarlo’s apartment and the neon fades a bit.

He lives in a ground floor studio with little back patio, an upright piano, a poster from the cult film “Over the Edge,” a farting, loveable bulldog named Rufus and, of course, books. Everywhere. Giancarlo himself could pass easily as a visiting Italian. Always well dressed, he’s a bit rough around the edges, cigarette constant in his mouth. He tells me he’s just talked to Gordon Lish, the infamous Knopf editor who edited Raymond Carver, Barry Hannah, Joy Williams and Amy Hempel, to name a few. Lish’s last book with Knopf was published in 1990s but his influence has garnered a cult-like worship from young writers.

“Lish couldn’t talk,” Giancarlo says. “He was on the other line with Don DeLillo.” Giancarlo has often been looked upon as Lish’s heir apparent, the Lish of the internet age. “He calls me Darling.” Lish has a cell phone? I ask. “No. House phone. He says my name comes up as Diazepam [the pharmaceutical name for Valium] on his caller ID.” Gordon Lish has caller ID? I ask. And two-way calling? “Yes,” says Giancarlo, “but he has no tolerance for computers. He calls it The Machine. I think he would be great on Twitter, though. Just one sentence. That’s his whole thing. He’s really missing out.”

Giancarlo is no stranger to the internet. Small presses like Tyrant couldn’t exist without it. Where Lish failed to reach a large enough audience, Giancarlo has leveraged social media to attain a worldwide audience at little-to-no cost. In the early 2000s, big presses raced to catch up with the internet, drawn by promises of free word-of-mouth advertising, only to find the small presses were already there.

I ask about Tyrant’s latest book, Marie Calloway’s what purpose did i serve in your life. The book ran into controversy reminiscent of the days of Joyce and Nabokov: the printer refused it due to the frank nature of the book’s sexual subject matter and lascivious photos of its author. It’s the kind of great “bad” publicity that every publisher dreams of. The book is polarizing; Publishers Weekly put it this way: “[Calloway is either] a sex-kitten, a feminist using her own body as a laboratory; or she’s a vapid internet-age narcissist.” Love it or hate it, the book is a hit — an anomaly for small publishers.

An unlikely candidate to become the face of the New York literary vanguard, Giancarlo DiTrapano was born in West Virginia. “My grandfather came from Italy when he was 14 to work in the coal mines. He saved enough money to go back to Italy and find a wife. He discovered a 17th century castelletto that the Americans had bombed during the war and the Nazis occupied. The gambler who owned it lost all his money and sold it to my grandfather for cheap.” Giancarlo’s family owns the castle to this day. His grandfather came back to the states and settled in Charleston, West Virginia’s largest city.

I ask about Giancarlo’s childhood. “My middle brother died in a car crash when I was nine,” he says. “My family went nuts for a while. He was the teen idol one.” Giancarlo, the youngest, looked up to his older brother and his death had a profound impact on him. I ask if he’s still close to his family. He says he just celebrated his father’s 85’s birthday in West Virginia. “My dad’s been through everything,” Giancarlo says “He lost a kid. He’s been hit by lightning twice, was hit by a train, been shot in the chest, and he once drowned and was revived by a priest.”

It’s not strange that Giancarlo seeks writing that involves life or death matters. But it also seems fitting that he engages the subject of sexuality, as in publishing Marie Calloway’s book. He is easily the straightest gay guy I’ve ever met. “Growing up, I thought about girls,” he says. “I was in love with girls. I beat off to girls.” But when he was 21 he began to find a certain kind of man interesting. “Bigger guys. Almost like Renaissance statues.” When I press about his emerging homosexuality he admits that he had sexual experiences with a counselor when he was nine years old. The counselor was a bigger guy. I ask if this might’ve had something to do with his later attraction. “I didn’t remember what happened ’til much later,” he says. “I started to remember images of his dick in my face. I don’t think it had that much of an effect on me. I just wish I could’ve been present, I might have enjoyed it more.”

Giancarlo went to New Orleans for college. Why New Orleans? I ask. “I didn’t want to go to school, but my dad said you have to go somewhere to college. So I took a boat out on the river. I got stoned and I hung my head over the side of the boat backward and looked at the river thinking about where I should go to school. A tugboat came by that said New Orleans on the top of it. So that was it. I had to go there.” He fell in love with the city. A philosophy major at Loyola, he was based out of New Orleans for the next five or six years, going back and forth to Italy. At the time he was still dating a girl he knew from West Virginia. They dated for 10 years in all before he came out of the closet. But they still have a close relationship to this day. “I just had dinner with her the other night,” he says. “She married a friend of mine. This is the best way. Now I’ll always have her in my life.”

After New Orleans, he headed to New York. I ask where his love of contemporary literature came from. “I’ve always been a reader,” he says. “Classics mostly. Then in college I discovered Sam Lipsyte. I found all these other writers through him. Just when the internet was starting and I could find all these people. Michael Kimball, Noy Holland. All these Lish dudes. I didn’t know who Lish was or make the connection until much later.” After New Orleans, Giancarlo headed to New York for an internship at FSG, but he became frustrated by the pace of it. “It would have taken forever for me to do anything I wanted to do,” he says. “But I had a little money, so I started a press.”

I ask about what’s next for Tyrant. “I’d love to put out Hob Broun. Sam Lipsyte and Lish have been suggesting I do this for years. Sam has an unpublished manuscript of Hob’s.” Hob Broun was edited by Gordon Lish in the 1980s. After Broun’s first book he became paralyzed from the neck down, following a botched surgery to remove a tumor from his spine. He wrote his next two books by expelling air from a tube that activated a keyboard. His books were cult favorites but are now out of print. This all seems somehow fitting. An underappreciated writer who, despite all, wrote through the suffering to reach some hard-won joy. I can’t help but see a parallel in New York Tyrant.

I wake up the morning after our interview in my girlfriend’s bed with no memory of how I got there. I text Giancarlo: “How did I get home last night?” He texts back, “I got you a cab.” I put my pants on to go downstairs and find a full pack of cigarettes in my pocket. My brand. Unopened. He must’ve bought them for me cause last time I checked I was out.

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Michael Bible is the author of Cowboy Maloney’s Electric City.