Looking Back, Moving Forward

observer guy

Illustration by Kyle T. Webster

I’ve been a fan of this newspaper for more than 20 years and its editor for less than three months. One of the things that people keep asking from me—demanding, actually—is that most noxious of modern conventions, “the elevator pitch.” Any idea that requires more than 30 seconds to explain is anathema in our 140-character culture, but what I love best about The New York Observer is how ferociously it declines to be reduced.

The New York Observer takes longer to explain, and it’s worth it. Nevertheless, here’s my best effort at a mission statement: identifying and chronicling the city’s most influential people in the world’s most influential city.

These days, a newspaper celebrating an anniversary is like a grandparent celebrating a birthday—one year closer to the grave. The Observer is bucking the trend. Our 25th year is on pace to be our best revenue year yet. While the paper remains our most visible face, our digital and ancillary businesses continue to thrive. As a paper that made its mark chronicling the media industry, The Observer has confronted the realities of our industry. The result: we are here, and we are growing, ensuring that this important voice will continue to be heard.

The New York Observer could not exist in any other city in America. New York is our country’s one world-class city. There are great cities all across America, of course. But there’s only one whose output is a daily concern to every other American. Or at least we New York City types think it is. And we think it’s adorable that we think it is. That self-assured conviction that the rest of the world is not only concerned but obsessed with what we think has provided the cornerstone of this paper for 25 years. And that’s why it’s growing beyond the city, as our websites evolve and links on Drudge and BuzzFeed and elsewhere direct people our way from around the world.

The New York Observer has always punched above its weight. No one will ever mistake our circulation for that of USA Today, nor our writing. Our goal, as the campus newspaper for the city’s powerful and influential, is to tell the story of the city’s actors. Not all of their stories—we don’t list every real estate transaction or catalog every media moment or cover every gallery opening. You don’t come to us for comprehensive news. You come for something that’s even more important: the meaning of the one transaction or moment or opening that everyone is talking about (or should be). These are the stories, large and small, that define the moment.

We’ve documented the shift in authority in the power class as it migrated from the Upper East Side throughout the whole city, first downtown and then to Brooklyn. We’ve been there, watching it and calling it, from the lows of September 11 to the highs of the first dot-com boom, from the days of open-air crack dealing in Bryant Park to the days of Cristal popping at Bungalow 8, from three great mayors and one who tried his best, to a Governor Cuomo to Client 9 to another Governor Cuomo.

Even our misses have been grand—if we were going to fail to notice the game-changing perfection of The Bonfire of the Vanities, at least it would be Francine du Plessix Gray who would be calling the characters “thin.” As Wall Street unraveled—Ivan Boesky wore a wire, an ambitious junk bond innovator named Michael Milken ran into the buzz saw of an even more ambitious prosecutor named Rudy Giuliani, and the stock market suffered its greatest-ever one-day dive in October 1987—Michael Thomas chronicled the recovery of the city’s most important industry in his beautifully titled Midas Watch.

Even 25 years ago, no one started a newspaper to get rich. By 1987, after the Hearsts and the Pulitzers and the Newhouses, it had already become clear that the only way to end up with a little money in the newspaper business was to start with a lot of money. Tilting against windmills, even our founding myth is totally Observer-y.

The Observer was born as Arthur Carter’s vision for a paper for people like himself—a guy who had made a pile of dough on Wall Street but was also a knowledgeable patron (and as an excellent sculptor, a practitioner) of the arts. To edit it, he soon recruited a young Graydon Carter, whose sensibilities had formed and been formed by the legendary Spy magazine. Soon after, Peter Kaplan grew The Observer into an incredibly fertile nurturing ground for talent of every variety, on every topic. As The Observer found its way, the paper fostered some of the greatest writers in the city. To name a handful is to omit a bucketful; just know that when you read any magazine or newspaper of consequence (or watch a bunch of TV shows and movies), it’s been touched by someone with pink-stained hands.

But all the while, operating out of Mr. Carter’s townhouse, where the staff literally wrestled over supplies, The Observer never really had a business plan. All the other media companies started to struggle, and we contended with what this is and what it should be. And now it’s getting there. Five years ago, in his intro to The Kingdom of New York, a compendium of The Observer’s first 20 years, Peter Kaplan wrote about the changes he and Jared Kushner began to enact on The Observer “to publish it as a paper for the new digital present, not the remote fading past.”

The New York Observer has been owned by two gentlemen who would be perfectly at home being covered in these pages. That means they are frequently the target of angry phone calls from people, sometimes close friends, who aren’t thrilled with the way they’ve been treated in our pages. We are lucky—and so are our readers—that both owners have resisted those calls and understand that our product relies on our readers knowing that we mean it when we say nothing is sacred but the truth.

Today the Observer Media Group is stronger than ever. Our highly opinionated writers help shape the national perception of New York. Our influence in the city continues to expand. We’re hosting the mayoral debates, we continue to be a force on all the local elections, we drive thinking about culture and art, and if our local sphere of influence is tight, it is also very real.

Even as The New York Observer consistently breaks national news, our goal is to continue to own the microcommunities of power that exist within the most powerful city in the world. Our paper is a reflection of NYC. The reason why this small, colorful enterprise is so beloved by so many is because we’re looking into the pond of the city and seeing the city’s reflection. Ultimately, that’s really our elevator pitch. Our pages reflect the city for everything it is: brilliant, beautiful, bad-assed, vain, impossible and sometimes cruel, yet absolutely intoxicating. The best character alive.


Looking Back, Moving Forward