Aug 10, 2015 · 14 minutes

Editor's note: This article originally appeared in NSFWCORP, which is now part of Pando. 

When I learned that Matt Drudge had linked to Matt Taibbi’s article, “The 52 Funniest Things About the Upcoming Death of the Pope,” I was on my way to volunteer at a children’s literacy center. 

During my two-plus years as editor-in-chief of the legendary, now-defunct alt-weekly New York Press, this was my indulgence. I didn’t fuck the interns. I didn’t take freebies from publicists. My kingly privilege was tutoring poor kids once a week.

I’m no do-gooder. In fact, I’m one of the worst lefties you’ll ever meet. I hate mouthy, earnest liberals and I generally despise The Nation. But helping poor brown children with their homework was a pleasant break from the never-ending grind of producing a weekly newspaper, particularly at a time when the industry was falling apart.

Looking back at the media landscape a decade ago, it’s nigh on unrecognizable from today’s. For starters, alt-weeklies still mattered. (Sort of, and not for long.) Copy editors and fact- checkers still had jobs. The words “professional” and “blogger” had barely met. But the world was changing, and we knew it. Craigslist was killing classified sections, specialized email blasts were making all-purpose event listings obsolete and web ads were eating away at their print counterparts.

Mom-and-pop print publishing was doomed. Accordingly, the age of the firebrand owner-editor-publisher was drawing to a close. Among the alt-weeklies, equity groups and consortiums were swooping in, eager to apply scale economies to film reviews and massage parlor ads. The founding editors and owners—once so perky when railing against Republicans, meat and minority injustice—were exhausted. They were being put out to pasture, voluntarily and otherwise.

The next generation, my generation, was eager to take the reins, to usher analog alt-weeklies into the daring digital age, to continue their forebearers’ tradition of fucking shit up. In 2003, I got my chance. And I blew it. 


Ten years ago, I was living in Prague, co-editing The Prague Pill, a biweekly newspaper founded by American expats Alexander Zaitchik and Micah Jayne. Stinging from a bad breakup, I was enjoying an enviable lifestyle in a literate, loose European city. In December 2002, my previous employer, New York Press, was sold by its founding owner and editor-in-chief, Russ Smith.

When I got word that longtime editor John Strausbaugh had left his post with the sale, I called Russ and asked for an introduction to the new owners. He kindly obliged, and a meeting was confirmed for the next day. I dug deep into my triple-digit bank account to invest in an early morning flight from PRG to JFK.

My interviewer was an affable old-media vet named Chuck who said New York Press needed to rebuild its reputation for being “the bad boys in town.” I couldn’t agree more. Little more than one year out from September 11, New York City still wallowed in somber, serious reflection. Irony had famously been declared dead by an old man lounging in a penthouse office (and good riddance). Irreverence, I knew, was primed for comeback. I convinced Chuck of my qualifications and landed the job with the provision that Zaitchik join me on the masthead. Our first issue hit the streets on February 25, 2003.

To meet Chuck’s bad-boy mandate, I threw down with my opening editorial. I described how a lovely, adventurous Australian woman once shoved a finger up my ass while blowing me on New Year’s Day in a hotel room just outside of Oxford. “Just relax,” she’d said, upgrading from pinkie to forefinger. “Just relax.” At the helm of New York Press, I would shove my finger up everyone’s ass. First the pinkie, then the forefinger. Just relax, I wrote, everything will be fine.

Apparently, bad boys didn’t accept fingers in their backside while getting head, even from Aussie bisexuals. Barely one week into the job, Chuck told me to tone it down. A few covers later, Joshua Cohen’s feature on the business of Jewish pornography prompted a second warning when the associate publisher, a flip-cup type named Doug, took offense with our cover headline, “Dirty Jews!” (In fact, he was too daft to take offense; his wife feared blowback from their dinner party pals.) Gritting my teeth, we changed the headline to “The Chosen Peephole.” Not bad, but not the same.

Doug was fired a few months later, and I’ve always regretted watering down that hed.

New York Press’ new owner was Avalon Equity Partners, an investment group headed by David Unger, an obese gay man who’d made his money in cable television. He’d bought the paper at a bargain price, which made his inept stewardship even more heartbreaking.

Working with Unger and his cronies was my first experience with hardcore business bastards. Don’t mistake me for a prissy purist. I don’t begrudge anyone for trying to make money. Profit drives industry, and quality editorial requires nothing if not industriousness. 

The fabled separation of church and state should indeed be sacrosanct. For me, it certainly was. But as editors climb higher on the masthead, they must at least occasionally join business meetings. They must hear their precious editorial endeavors discussed in frank fiscal terms. They must understand that, for most publishers, editors are nothing more than a necessary evil for delivering readers.

Meetings with Avalon were an extraordinary education.

Once, in an attempt to save a job in the neighboring production department, I trimmed my own budget to match that position’s salary and benefits. I tightened word counts; I suspended those few editorial perks that remained; I asked some contributors to voluntarily cut their rates. (One casualty: I dared to ask cartoonist Tony Millionaire to accept $50 less for his syndicated comic Maakies, which then commanded an outrageous $200 per week. Insulted, he pulled the strip and we never spoke again.) My efforts were rebuked. The overlords didn’t want to save actual dollars; they needed fewer heads to satisfy whatever metric suggested a more valuable business.

I was a fool. Finance guys live and die by ratios, not balances.

Again, I’m not immune to the realities of industry. At a certain level, all editors must become business-minded. For this reason, my corporate bosses actually liked me. I wanted a high ad-to-edit ratio: With every third ad page, I’d get one of my own. I rarely bitched when my pages were cut for last-minute ad buys, and I even launched or expanded sections to help salespeople attract new clients.

Things changed when we described the cast of “Queer Eye for the Straight Guy” as “annoying faggots” in print. To call David Unger mad would be an insult to his anger. I did my best to explain the need for aggressive expression in this pussy-ass world. I explained that “faggot” wasn’t such a bad word anymore, precisely because of this sort of casual, benevolent use. It was like trying to explain Schrödinger’s Cat to a retarded walrus.

“You can’t use that word!” he bellowed. “You’re not one of us!”

“Just to be clear,” I asked, “if I were gay, my job wouldn’t be on the line?”

“That’s right. You’re not one of us.”

Looking back, that’s a little bit illegal.

The fact is, I’m not homophobic. Nor am I particularly anti-Catholic. I was never the former, and I’ve grown out of the latter. But I’m also not concerned with the line between good and bad taste, as long as the result is funny or poignant. Point being: By the time Matt Taibbi filed his Pope column, we’d committed far worse sins.

To wit:

  • On the cover of our debut issue, we called Al Sharpton a negro.
  • To illustrate Douglas Rushkoff’s feature on the decline of institutional Judaism, we dressed my friend Jon as a Hasid and wrapped him in explosives. Headline: “Suicide Jews!” 
  • To accompany Paul Krassner’s commentary on “The Reagans” miniseries, we depicted a near-death Ronald Reagan, drool dripping from his chin; in the background, Nancy sucks off his doctor. 

Pando’s own Mark Ames wrote a ruthless, cruel (and deserved) takeout of Chuck Klosterman, describing his mouth as “a sphincter twisting to a pained close 40 seconds after taking a brutal pounding from Peter North.” 

Except for some internal protests—usually lodged by interns and other earnest youngsters—no one strenuously objected to my work. Controversy brings readers, and my job was to deliver readers. Salespeople, in turn, deliver those readers to advertisers. On those rare times he was forced to scold me, Chuck the publisher always picked up the bar tab. 

The real problems began when Chuck himself was put out to pasture, replaced by an alt-weekly twat from Las Vegas named Chris. In publishing, few executives are more dangerous than the carpetbagger with something to prove. One way or another, this rube needed to make his bones in the big city. 

Before we left Prague, I told Zaitchik to expect a clear runway for two years. The first 12 months would be amazing, I promised: The new owners would be too preoccupied with balance sheets to pay attention to the editorial wing. In year two, I said, they’ll cast glances our way, not entirely comfortable calling Al Sharpton a negro on the cover. In year three, the business will still be a fucking mess (because the industry itself was simply fucked), and they’ll start looking for a scapegoat. Editorial is always the scapegoat.

Sure enough.

Contrary to popular opinion at the time, we weren’t courting publicity with Taibbi’s Pope column. He’d actually written “The 52 Funniest Things About the Upcoming Death of the Pope” 
as a throwaway during a creatively fallow week. This was 2005. There was no Twitter, and essentially no Facebook, Reddit or Digg. When you published something in a newspaper, you also published it on your website and hoped they would come.

Here's how an article caught fire in 2005:

  • On Tuesday, March 1, NewYorkPress issue no. 9, 18th edition, hit the streets and went live at 
  • The editorial department immediately forgot about issue no. 9 and began working on issue no. 10. Just another week at the office 
  • At 9am GMT on Thursday, March 3, Drudge slapped the Pope story on his front page with the all-caps headline “OUTRAGE: NEWSPAPER LISTS ‘52 FUNNIEST THINGS ABOUT THE UPCOMING DEATH OF THE POPE’...” 
  • Zaitchik called me on my cellular flip-phone and told me the good news. 
  • Our servers crashed. 
  • Never one to miss an opportunity to suckup to bold-faced names, the Daily News’ Lloyd Grove sought comment from local politicians. 
  • Hillary Clinton said she was disgusted. 
  • The mayor’s office was horrified. 
  • Congressman Anthony Weiner (yeah) urged area Catholics to throw out as many copies of New York Press as possible. This is a federal crime. 
  • Senator Chuck Schumer called the article “the most disgusting thing I’ve seen in 30 years of public life.” Thirty years, incidentally, included the Joel Steinberg case, the dismembering of Rashawn Brazell, the Central Park jogger rape, Amadou Diallo, Joel Rifkin, Son of Sam and a certain Tuesday morning when two jumbo jets fell out of the sky. 

That night, I appeared on NY1 to answer for my crimes; I took the free-speech route. The next day, I made a few radio and TV appearances, further defending my constitutional right to be a dick. On Friday night, I was interviewed on “Scarborough Country” alongside a reprehensible fetus-obsessed Papal apologist named Bill Donohue, from the Catholic League. Another spittle-flinging walrus, Donohue called me a “little brat” and described my paper’s upstanding advertisers as “male and female perverts, ACDC, switch-hitting, pineapple upside- down cake, fruity-tooty people.”

Which is hilarious.

The high point of my week was calling Bill Donohue “a rabid, homophobic Catholic nutcase” on national television. To celebrate, I went on a two-day speed binge. Such are the peak moments of one’s life.

During my first stint at the New York Press, as production editor in the 90s, I jumped at every chance to learn from the paper’s then-editors: Russ Smith, John Strausbaugh and Sam Sifton. This was the Press’ Golden Age, when the week’s bylines regularly included William Monahan, Mike Doughty, Dave Eggers and Jonathan Ames, to name just a few. Watching the oft-stressed relationship between editorial and advertising, I learned that publishers reliably freak the fuck out when blowback threatens ad sales. It’s the editor’s job to convince them that bold brand reinforcements (not to mention truth, integrity, uncompromising journalism, etc) are actually good for business.

Under Smith, spearing a blowhard like Bill Donohue on a national platform would have been cause for applause. But the Golden Age was over: Smith had moved to Baltimore; Strausbaugh was writing books; Sifton was a rising star at the New York Times. My new bosses were not men, but algorithms made flesh—floppy, pale flesh—and built to interpret spreadsheets. First thing Monday morning, clearly collapsing under the pressure of controversy, the carpetbagger publisher called me into his office.

He tried to suspend me for two weeks, without pay, and insisted that I publicly apologize for Taibbi’s article.

If you’re a pussy, there’s a reasonable argument for taking the pussy’s path. Here was a career salesman with kids, car payments and a suburban mortgage conspiring to strip away what little dignity he may have brought to the job. For better or worse, I had no such burdens. When told to apologize, I refused and resigned on the spot. I sent an exit letter to Gawker, setting off another shit storm. That night, I was back on MSNBC—this time, listed as a “top newsmaker” on “Countdown with Keith Olbermann.”

Surely I could’ve found another editorship—as an energizing right-hand to a wistful ex-firebrand now muffled by his corporate paycheck, for example. If there’s one thing that editors admire, it’s a fellow editor risking his job for their integrity. But I wasn’t in the mood. I was sick of working behind a desk, sick of fighting with salespeople and spineless publishers. Instead, I sold everything in a whirlwind, crank-fueled apartment sale, lined up some freelance work and hit the road.

 Second only to investing in that flight from Prague, refusing to apologize was the best career decision I ever made. For a year and change, I backpacked around the world, filing with the New York Times, Maxim UK,, Radar and other legit outlets. I lived low, wrote a lot and enjoyed the typical expat indulgences. Soon enough, I fell in love and found myself back in New York City, serving as deputy editor of Forbes Traveler.

When that went belly-up, I worked again as a full-time travel writer, struggling to file meaningful assignments without succumbing to the easy path of press trips, junkets and PR suckjobs. I did a few months at Travel + Leisure. I got married. We got a dog.

New York Press was shuttered by its next owners, Manhattan Media LLC, in August 2011. In September 2012, the Village Voice’s editor of five years, Tony Ortega, resigned. He cited a time-consuming book project, but I suspect he’d endured enough meetings with ratio-obsessed corporate overseers. He’d fired enough staffers and suffered his share of page cuts. To be sure, the Village Voice is a loathsome product, but... I emailed Village Voice Media’s executive editor and applied for the job. Yes, I wrote, I could pilot this legendary title into a new era of relevance and recognition. No, I assured her, I wasn’t afraid to make difficult decisions. Funny thing is, I actually meant it.

I never heard back. Which is probably a good thing for all involved.