Longreads Member Pick: Jason Zengerle's First Assignment for Might Magazine

This week, we’re thrilled to feature Jason Zengerle, a contributing editor for New York magazine and GQ who has been featured on Longreads many times. Our Member Pick is Jason’s 1997 story on Michael Moore for Might magazine: “Is This Man the Last, Best Hope for Popular Liberalism in America? And, More Importantly, Does He Have a Sense of Humor?”

Jason explains:

This was the first story I wrote that could qualify as a long read—and it certainly wasn’t by choice. I’d just graduated from college and was doing an internship at The American Prospect, but I spent most of my time daydreaming about being an intern at The New Republic, which hadn’t seen fit to hire me. Hoping to change their mind, I’d routinely pitch TNR freelance stories, and one day I got the idea to write a takedown of Michael Moore: I sent in at a tightly-argued, perfect-for-TNR 1,000 words; TNR sent back its customary 20-word rejection. That would have been the end of it, but I showed the piece to my friend Todd Pruzan, who offered to show it to his friend Dave Eggers, who was then editing a little magazine called Might.
It turned out that Eggers didn’t share my dim opinion of Moore, but he did see the potential for a fun stunt. He said Might would be willing to take my 1,000 words arguing that Moore was a hack, if I’d be willing to embed them in a much longer shaggy-dog story of trying to track down and meet with Moore himself. By now, of course, the idea of pulling a Roger & Me on Michael Moore is pretty played-out, but at the time, I don’t think anyone had thought of it yet. And so on MLK Day weekend of 1997, I took a Peter Pan bus from Boston to New York, rented a gorilla suit for my unemployed actor friend Morgan Phillips, and set off on our little adventure.
The rest is history. By the end of that year, Might was out of business. Eggers was writing A Heartbreaking Work of Staggering Genius and on his way to becoming the voice of a generation. And I was an intern at TNR.