Dirty Harry Siegel takes over the New York Press

When New York Sun writer Tim Marchman and his wife moved to Chicago in 2003, he mentioned that they would have to move back to New York if he and his friend Harry were ever in a position to take over the New York Press.

Tim and Harry had been friends since Harry’s first year at Long Island University. They would often talk about their journalistic ambitions, fantasizing about seizing control of various publications. Their most realistic scheme concerned the New York Press. Long fans of the free weekly’s mix of contrarian politics and downtown culture, they considered it ripe for invasion. But for years their plan came to little more than a drunken, early-morning incident involving verbal assault on a receptionist at the offices of the Village Voice (close enough).

Marchman went on with life, becoming a sports writer for the New York Sun, marrying, moving, and starting a family. Harry, too, worked at the Sun and freelanced around. But this spring, Harry began talking to New York Press founder Russ Smith, who had a very low opinion of the newspaper’s quality of late. Preparation meet opportunity. Soon enough, Siegel was sending out the bat signal to Chicago, calling the Marchman family back east.

Smith had sold the Press shortly after 9/11. But the two interim editors–first Jeff Koyen, then Alex Zaitchik–had quickly flamed out. Siegel and Marchman’s failed siege of the Voice impressed Smith. A fan of and occasional contributor to Siegel’s website New Partisan, Smith met Siegel this summer at a meeting with the Press‘s current ownership. He found his successor to be “an intense guy, bursting with ideas, and I was glad to give him my unqualified recommendation.”

Siegel cut his teeth at the New York Sun. Hired as a news assistant, he was given 25 minutes for his first writing assignment. He went on to write local editorials for the Sun for the better part of a year. He soon burned out and quit, then went through a dance of returning, quitting, and being fired for another few months before finally leaving the Sun in early 2004. Siegel went on to freelance, work on a book, and launch the New Partisan–a tribute to the late Partisan Review–before getting in touch with management at the Press this spring. Siegel’s former (and my current) editor Seth Lipsky refers to him as “a cross between a genius and an ency-clopedia and a natural born newspaperman.” Siegel’s nickname at the Sun was “Dirty Harry”–due to both his reporting style and the state of his desk. Lipsky’s one complaint regarding Siegel’s tenure at the Sun was that “he couldn’t get to work on time, which was frustrating because he worked only a twenty hour day.”

Siegel has translated that work ethic to his new position at the Press, where he sucks through cigarettes as though he’s subsidized by Philip Morris. Yet, working out of their garment district offices seven days a week has civilized Siegel after being a full-time freelancer: “Getting dressed passed my underwear is a new thing for me.”
Smith started the Press in 1988 as a pugnacious alternative to the Village Voice. Siegel, who says he’s a Democrat, is still more right of center than the Press‘s interim editors. He is inclined toward social liberalism and economic conservatism. Above all, he says, he is averse to like-mindedness.

In any case, Siegel doesn’t want to brand every page of the paper with his own politics: “I learned from Lipsky that a paper has a voice of its own, and you have to respect that.” He feels the interim editors produced a paper that was “monotonously left-wing, excluding Russ Smith, [whose “Mugger” column] they pretty much had to run. It was . . . like The Voice.”

Siegel thinks the Voice is a disaster. He hopes to have slots for at least one conservative and one liberal writer in the front of the paper and a wide variety of opinions throughout.

Another problem, Siegel says, was the insularity under Koyen and Zaitchik: “It felt like a buddy paper–and mine does too, but hopefully that will change.” Siegel has brought in his own set of friends like Marchman, playwright/journalist Jonathan Leaf, and Azi Paybarah onto the staff, but there’s no shortage of writers in New York looking for outlets.

Displeased with the current shift in the media toward shorter pieces–“writing for subliterates” Siegel calls it–Siegel wants to run longer pieces, pieces judged on their merit, not the writer’s proximity to the editor.

He also wants to run certain kinds of writing no more than a few mainstream publications are even willing to consider anymore–fiction and poetry. Along with jazz writing and cartoons, the paper will also feature a cantankerous letters page.

While the Press under Siegel will cater to what he calls “the tin-foil hat people and schizoids” who have always embraced the paper’s anarcho-libertarian qualities, he wants to draw in the three percent of local readers who really might be considered swing voters. The people “whose politics shifted after 9/11–whichever way–because they thought it out and realize this was a consequential event. I want to write for those people.” Siegel is not entirely unsympathetic to the plight of his predecessors Koyen and Zaitchik (whose tenure at the Press was short-lived after they published an infamous humor piece by Matt Taibbi on the death of the pope). While he disagrees with much of their politics and editorial decisions, Siegel acknowledges there were budget constraints and content decisions that were beyond their control.

Nevertheless, Siegel’s optimistic about his own ability to navigate these pitfalls: “If you put out something that’s smart and not concerned with the bulls–, I’m confident that there’s a big readership out there for that, and I’m now about eight months away from being confirmed wrong.” Siegel sees a huge market for longer, more interesting writing, and Smith, for his part, thinks Siegel uniquely qualified: “My hope is that Harry can restore order and dignity to New York Press, and he’s already on his way.”

Of course, this approach may not work. But Siegel seems ready for that, too. If his efforts should come to naught, he says, “F– the reader, f– the advertiser, and f– everyone else.”

This motto is actually in keeping with the punk ethos of alternative newspapers everywhere, and especially the New York Press.

Meghan Keane is deputy culture editor of the New York Sun.