A few months after buying the Observer, Jared began dating Ivanka Trump. Behind the “Page Six” fodder, the pair are a genuine match. “Jared and I are very similar in that we’re very ambitious,” Ivanka tells me one morning in her office on the 25th floor of the Trump Tower. “That’s what makes it so amazing to be in a relationship with someone who is supportive of that. I’m happy for him when he is in the office working late. I know how good that feels when you sit down and return e-mails.”
Dating Ivanka was fraught with family peril. Though she is converting to Judaism, studying with Rabbi Haskel Lookstein at Congregation Kehilath Jeshurun on East 85th Street, it has not always been easy. Jared’s mother, in particular, has struggled with their relationship. Last summer, Seryl told Jared to cool it. They broke up for a time but soon got back together.
Ivanka told me she and Jared plan to marry, but they aren’t officially engaged. “I am studying,” she said of her conversion, “and it’s been an amazing and fulfilling experience for me … One of the jokes I first started making when Jared and I first started dating is, I’m a New Yorker, I’m in real estate. I’m as close to Jewish, with an ‘i-s-h’ naturally as anyone can start off.”
When Jared bought the Observer, he and Peter Kaplan positioned themselves as partners. “I had no vision for what it should be,” Jared says. Kaplan would teach Jared how to be a publisher. Kaplan was a storyteller, a protégé of New York founder Clay Felker’s, and a lover of old Hollywood whose mordant wit, Yiddish-inflected headlines, and casual regard for deadlines made the Observer a literary playground for young talent, a kind of postcollegiate newspaper. He liked to tell his writers to imagine the paper as a kind of Victorian novel.
In truth, Jared and Kaplan’s relationship swerved between grudging respect and conflict. Though they grew up in the same part of New Jersey and both went to Harvard, in other ways they were the oddest of couples. Jared found a lot of the paper incomprehensible and fuddy-duddyish, while Kaplan couldn’t quite get over the fact that Jared was the same age as many of his reporters. Kaplan at first tried to mentor Jared like one of his writers. But that only worked for a while. Six months into owning the paper, Jared hired Bob Sommer, a former publicist whose New Jersey communications firm represented the Kushners, to be president. “When I first hired Bob, I said, ‘I’m so happy you’re here,’ ” remembers Jared. “He said, ‘Why? Because I’m helping you?’ And I said, ‘No, because no one would believe what was going on here if I tried to explain it.’ We called it Weekend at Bernie’s, because it was like dead people walking around.”
In April 2007, after the New York Post reported the Observer had missed newsstands, Jared was furious. He told Sommer to force Kaplan to get the paper to press no matter what, leading to a shouting match between Kaplan and Sommer.
Jared pushed through a redesign that essentially created two front pages, and added a real-estate section. He also insisted on shorter stories and drove Kaplan to shovel stuff onto the web, which Kaplan thought was the wrong strategy. “We had benchmarks,” Sommer says. “And Peter hated it.”
Last fall, Jared told Kaplan he needed to cut the Observer’s budget. A 2007 plan to launch a national network of political websites had failed, and now he needed to pull back amid the recession. He wanted layoffs. Kaplan resisted, asking writers and editors to take a 5 percent pay cut and leaving positions unfilled. Jared insisted on even more cuts. Finally, in late March, Kaplan told Jared he was going to resign when his contract was up on June 1.
It is deeply frustrating to Jared that the Observer continues to lose money, partly because the media business is a way for him to make a name as a businessman independent of his father. Content-sharing deals with the Huffington Post and Politico stalled. The New Jersey website Politicker NJ, while small, is a success he takes pride in—he say it makes a small profit. “It dictates the political agenda in the state of New Jersey,” he says. In mid-June, he bought Very Short List, the highbrow e-mail newsletter backed by Barry Diller, and claims it’s already profitable.
For the Observer job, Jared reviewed twenty résumés and ultimately gave deputy editor Tom McGeveran the interim position and a bare-bones budget. McGeveran is said to have believed that if he didn’t accept the budget, Jared would give the job to former Village Voice and New York Press editor David Blum, who had been lobbying heavily for it, saying he could run the Observer for a rock-bottom $900,000. “I didn’t expect the public side of this,” Jared says. “And I didn’t expect to be walking into this at the worst time to be buying newspapers.”