Who

Kaplan is editor-in-chief of the New York Observer, the Jared Kushner-owned salmon-colored weekly that serves media obsessives and residents of the 10021.

Backstory

The New Jersey native's ties to the rich and powerful go back to his undergraduate days at Harvard, where one of his roommates was Robert Kennedy Jr. Kaplan started his media career in the mid-'70s at ABC Radio; he later switched to print and spent a decade writing for the New Times, Esquire, the Washington Post, and the New York Times, where he covered the TV industry. He left the Times to serve as executive editor of Manhattan Inc., a business title edited by Jane Amsterdam and Clay Felker (who also founded New York). When the economy settled into a recession following the stock market crash of '87, Manhattan Inc. folded and Kaplan launched a new publication called Smart for Men.

By the early 1990s, he had taken a job at Condé Nast Traveler (despite, he says, knowing little about travel), but left after a year to sign on as executive producer of Charlie Rose's new talk show on PBS. When the editorship of the Observer opened up a year later following the departure of Graydon Carter, Kaplan skipped out on Charlie and took the job. He's been there ever since, weathering financial difficulties and, in 2006, a dramatic change of ownership.

Of note

For more than a decade, Kaplan worked under Arthur Carter, the former investment banker who founded the Observer in 1987. Targeted to the city's most affluent demo, the paper has long enjoyed a good deal of influence with the media and political elite. But it's never been much of a moneymaker and steady losses over the years forced Kaplan to make do with a relatively skimpy budget and rely on a staff of junior (cheap) writers and editors. The mounting losses—and his mounting age—led Carter to the negotiating table several times over the years. But despite numerous discussions with potential buyers (he came close to selling it to now-disgraced press baron Conrad Black in 1999), the paper continued to linger on the market as well as hemorrhage money, as much as $2 million annually in recent years.

Carter finally worked out a deal to sell the Observer in 2006. After his first plan fell though—he was in discussions with Tribeca Enterprises' Craig Hatkoff, Jane Rosenthal and Robert De Niro—in July of 2006 he sold the paper for $10 million to Jared Kushner, the son of disgraced real estate developer Charles Kushner. Kaplan stayed on as editor—and reportedly received a small equity stake as part of the transaction—and now reports to the youthful real estate scion, who is nearly 30 years his junior.

In 2007 the paper underwent a tabloid makeover and the website was re-launched. The editorial has shifted as well: The articles are shorter, the real estate coverage has been beefed up, and the stinging wit has been toned down a bit. These days you'll find the last few pages filled with puff pieces about Jared's colleagues in the real estate industry.

For the record

The Observer has long had a reputation as a launching pad for writers and editors. Most notably, Candace Bushnell wrote her column at the Observer before she went on to fame and fortune. (It was Kaplan, in fact, who coined the column's name, "Sex in the City.") Other alums include Nick Paumgarten, Alex Kuczynski, Warren St. John, Jim Ruttenberg, and Charles Bagli.

True story

In 1998, Kaplan was in the running to take over as editor of the New Yorker following Tina Brown's departure, and reportedly met with Condé Nast chief Si Newhouse about the job. David Remnick got it instead.

Personal

Kaplan is divorced from his first wife, Audrey. He's now dating Elle editor Lisa Chase and living in Larchmont.