Greg Osberg: Maybe Not Such a Savior of the Inquirer?

A writer ponders how he missed the signs of the exec’s implosion.

Well, I must admit: I didn’t see all this coming. From the trainwreck Greg Osberg has made of his administration at Philadelphia Media Network to the emergence of Jeffrey Perelman as a bidder, the last month at the Philadelphia Inquirer, Daily News and philly.com has run counter to expectation.

Back in the winter of 2011, I wrote a profile of Greg Osberg in which I assessed the chances of a business turnaround at this city’s newspapers as low but lauded Osberg as fitting the template of a possible savior: A longtime Newsweek business executive, who embraced the Internet way before the majority of his print publishing competitors; a guy who led a dot-com—CNET—to profitability, a rare feat on anyone’s resume; and a man with a real love for technology, as opposed to a fear of what it’s done to his industry.

Those things remain true, as far as they go. But they didn’t go far enough.

In the last month or so, soon after it was announced that the semi-regular sale of Philadelphia’s newspapers would recommence, we learned just how ill suited Osberg is to this work.

Instead of running the newspapers, he has engaged in a battle with its editorial staff. Reporters and editors at the Inquirer and Daily News believed coverage was being rigged from above to support the bid of a group led by Ed Rendell.

On February 6th, an Inquirer story about a possible bid from developer Bart Blatstein was spiked before it could run. The next day, Osberg’s spokesman, Mark Block, removed a post from the DN’s Philly Clout blog, which named potential bidders other than Rendell’s group.

From there, Osberg compounded his own problems. According to a February 15th New York Times article, Osberg told reporter David Carr, three times, that he had not convened a meeting with his top editors, informing them that he would be overseeing coverage of the sale. Carr and co-reporter Amy Chozick had already verified the meeting with multiple sources.

“I asked Amy afterwards,” Carr recalled later, in an interview with Jim Romenesko, “‘Do you think he choked? Why did he do that?’ We really couldn’t figure it out because word of that meeting was all over the building.”

Now, contrast this with this quote about Osberg, from longtime Newsweek editor Rick Smith, which ran in my feature: “Greg has a finger-tip understanding of what the needs and goals of editorial are,” he says, “which I, frankly, don’t understand how he got coming from the business side.”

More to the point, Osberg’s old colleagues like Smith and another former editor, Mark Whitaker, described a culture in which advertising and editorial mixed more than they might at most publications, exchanging ideas and respecting each other’s input. This is tricky business, crossing the boundary between advertising and editorial. But, I was assured, Newsweek was able to do it because the people involved, including Osberg, understood and valued the ethics of journalism and understood where the lines were drawn.

Imagine my surprise, horror even, when the events of the last month unfolded. I understood that it was highly possible that Smith, Whitaker, and a half dozen other sources might have felt the need to be politic about Osberg as he embarked on a new job. But the portrait they painted for me went way beyond the sort of platitudes people employ in that scenario. I got none of the empty “good guy,” “fine gentleman” stuff I’ve heard on other stories, about other subjects. So in recent days I called Smith, and Whitaker, among others, hoping to get some clarity—to find out if they were as surprised by recent events as I had been.

I’ve yet to hear back from Whitaker, but I did reach Smith. He was, understandably, almost speechless when I asked him about Osberg’s recent behavior. “I did see the Times piece, and I have no direct knowledge of what went on. But I have to say that as the story as reported, if it’s true, I found it … very, very … puzzling.”

Smith, now the president of a New York foundation aimed at preventing juvenile delinquency, hasn’t spoken to Osberg since he took over Philadelphia’s newspapers. Just because they’re both busy. But he worked with him for more than 10 years, and as he tried to enunciate his thoughts, lapsing into long, pained silences, it was clear that recent events just did not square with the Osberg he’d known. “I even had lunch with a fellow former colleague from Newsweek, and of course this came up and we had no explanation.”

So, what’s up with Greg Osberg? Well, at least a couple of his old colleagues have no idea. And in hindsight, there is one aspect of my reporting I wish I had communicated to readers in my initial profile. As I journeyed about the newspapers’ headquarters, every interview I conducted with the highest-ranking staffers at the Inquirer, Daily News and philly.com was attended by Block, Osberg’s spokesman.

This little maneuver is not unknown, and in corporate settings it’s common for some “handler” to sit in on interviews and take notes along with the reporter. The arrangement is awkward, at best, and though PR folks usually couch it all in friendly terms—“we just like to keep a record of what’s said”—the overall effect is chilling. The person being interviewed knows they better be careful that every word they say is company-approved. There is zero opportunity for sources to go off the record or impart important information on background. And the reporter is also now aware that, if the final story ever results in a lawsuit, there will be a competing set of notes.

As I said, this sort of thing is common in corporate cultures—where the truth is something to be managed and controlled. But at newspaper companies? The idea that any journalist would be accompanied by a corporate lackey while they give an interview is anathema to the transparency newspapers normally foster in their own operations and request from sources. But even after I suggested this much to Block, he kept turning up, pen and paper in hand, scribbling more furiously, frankly, than I did.

Looking back, this was the one thing I saw that suggested Osberg lacked real appreciation and understanding of the papers he had come to control. But the real key to Osberg’s recent unravelling was probably right there, all along, in his resume.

He never did ascend to the top post at Newsweek. He always did have a boss to whom he reported. And there is, at the end of the day, a big difference between being The Guy and being the person who sits next to The Guy. So, to re-appropriate the question David Carr asked, “Do you think he choked?”

Well, yes. As a matter of fact, yes, I do. I only wish I’d seen it coming.