But, with his contract up for renewal in June for the first time since 28-year-old real estate scion Jared Kushner bought the paper in 2006, he decided to step down. Now, the paper belongs to Kushner. (Kaplan said he has agreed to consult on the search for his replacement.)
He told his own paper that he made the decision to quit because "I wanted to take care of my family." But talking with us, he didn't sound like a man who was on the verge of retiring. "New York and the media and me are the most fun combination I can think of besides my kids," he said. "I would like to be able to see whatever cultural foundations that made up New York Observer hop ahead into the new world."
But as the proving ground for an entire generation of reporters and editors (full disclosure: Kaplan gave me my first job out of college), the Observer has been one of New York City's cultural foundations, introducing both a cast of characters (the "power elite," as he often put it) and a mode of covering their squabbles, mores and foibles that has been duplicated everywhere from prestigious newspapers to lowly gossip blogs.
It always seemed to be an awkward match when Kushner became Kaplan's boss — like a fox buying the henhouse. His dad, Charles, and his conviction on corruption charges had been richly covered in the Observer, and the editorial changes he made after the purchase — bulking up coverage of real estate business and local politics — only seemed to further entwine the paper more heavily in the spheres of influence his family most cared about.
After work, Kaplan was more likely to catch the train back to Westchester than join the city's social conga line. Last night, as his prized editor was closing his last paper before quitting, Kushner was attending a Tribeca Film Festival party with his fiancee Ivanka Trump. (That's him in the pic on the right.)
The biggest task on Kushner's plate when he became publisher — figuring out how to bring the paper into the Internet era — has also been his biggest failing. The paper has been crowing about its recent award nomination — on its site, the motto "Nothing sacred but the truth" has been replaced with the stirring "2009 Webby Nominee Best Newspaper Web Site" — but its recent redesign has made it virtually unnavigable. It's frustratingly difficult to find anything that isn't featured on the front page. After last week's amazing Hipster Grifter feature caught traction, its writer Doree Shafrir established a dedicated page for her mid-week web-only follow ups. I saw it once, but I can't find it now. (Ah, here it is.) As the New York Times' David Carr noted, that opened the door for us to run wild with follow-ups as the meme spread.
The perpetually khaki suit-clad Kaplan has always prided his salmon-hued paper's reporting above all. He is no fan of the commentary-heavy Internet. (One of the maxims I remember him repeating is, "attitude is cheap, reporting is expensive.") But whatever he does next, it sounds like it will be digital. "I want to think about some stuff in the media that is interesting to me in terms of the new world," he said. "We're at this incredible moment and I would like to be part of the inculcation of what happens next."