It's incredibly difficult to keep a secret anymore, and in this adolescent media world, it's impossible. So: I assumed, because Greg hadn't been blowing cash and buying everybody drinks and hookers over the last three months, that he had lost on Jeopardy. We'd known about this for a while, and a bunch of us had even helped him study. I was even a little concerned; he was putting so much effort into winning that I feared what would happen if he lost. Every pseudo intellectual has dreamed of being on Jeopardy. Actually making it, and then getting crushed, could emotionally devastate even the most stable of us. So I worried Greg was doomed. Halfway through Double Jeopardy, my worry was not displaced. All of us had gathered at the Barrow Street Ale House, hoping to cheer Greg on, but he was so far behind that our priorities changed. No longer were we, "Way to go, Greg." It became, "Christ, how the hell do I deal with the crying dude when I just want to leave already?" And then he caught a break, and hit the second Daily Double, and then entered Final Jeopardy within distant striking distance. At this point, we were just happy he'd made it that far. He had nothing to be embarrassed about. I was trying to imagine a scenario where Greg would feel comfortable inviting people to come watch his show without him actually, you know, winning. This seemed about right. Within striking range during Final Jeopardy. Close enough. Good show, son. Everyone back in Illinois is surely proud. And then the crazy defending champion woman missed — honestly, Galileo was obvious; she totally choked — and, somehow, amazingly, Greg had won. I write about sports a lot, more than I'd like, actually, and I find that the more sports I watch, the more difficult it becomes to come across an outcome that's truly unexpected. The term "upset" has become trite. Even the scrappy underdogs make millions and, if you met them in real life, would not like you. But to actually watch a friend of mine come from nowhere — seriously, the man was defeated — and win, in front of everyone he knows and holds dear (and even a few he doesn't) ... well, not even this cynical Brooklynite could deny it. About 35 jaded, angry, jealous, winded media people, everyone sniping behind everyone's backs beforehand, apoplectic that THAT guy got THAT assignment, all in a room together ... suddenly screaming like we're 10 year olds, shocked, giddy, foolish. It was awesome. This is all giving Greg a bigger ego. But it's true. The place went nuts. We were all so happy. He's on again tonight, and maybe he'll win, and maybe he'll lose. Honestly, after the first unexpected victory, it turns strange, really, to cheer for your friend to make more money. This is New York, after all, and more money could mean a better apartment than I have, and That. Just. Won't. Do. But for one night, we were all Marshall. Update the Greg Lindsay Career Trajectory, folks. My friend is a Jeopardy champion. So, now that he's won on Jeopardy ... maybe he can finish his goddamned book.
Greg Lindsay comes across as an uptight guy. But that doesn't stop him from appearing on television again and again. Indeed, he's the poster boy for go-getters who try on every form of media until they find one that fits best. The former WWD gossip columnist and author of a book about sleeping in airports landed a "memorable" appearance on Martha Stewart's TV show earlier this year. And last night, he was a contestant on Jeopardy! The secret to his publicity, he advised a youngster long ago, is to remember "it's all about the brand called you." And how! Click to watch the clip of Lindsay's, um, uphill battle. And we'll let former Deadspinner Will Leitch finish the story of watching the show with Greg himself: