If the nation’s top newspaper publishers could have played nice back in the early 1990s, the Tribune Company would not be bankrupt, newspapers would not be dying, and Google would, at least, look very different today. This is according to James O’Shea, who has written a new book about the disastrous merger of Tribune and Times Mirror Corporation, called The Deal From Hell (Public Affairs, hardcover).

O’Shea joined the staff of the Chicago Tribune in 1979 and rose to become its managing editor in 2001, shortly after the Tribune bought out the much larger Times Mirror. The merger was trouble from the start, and the company sold itself to real estate investor Sam Zell in 2007 for about $13 billion, almost all of it borrowed. To make those heavy debt payments, Zell and his people demanded even larger cuts to the company’s staff, particularly to the reporters at its newspapers, including the Los Angeles Times, Orlando Sentinel, Hartford Courant, and our own Baltimore Sun. Those cuts decimated the news-gathering abilities of the papers and sapped morale. To manage the sprawling company, Zell employed a veritable morning zoo of former radio-station managers who, when not penning unintelligible memos, allegedly spent their working hours sexually harassing female staffers. This failed to improve the company’s business prospects, and Tribune filed for bankruptcy protection in 2009.

O’Shea’s book chronicles the events of the past decade and places them within both companies’ storied and proud histories. Short-sighted, Wall-Street-oriented management killed the newspaper business, he argues—but it started at least a decade before the ugly denouement.

In 2006, O’Shea was named editor of the Los Angeles Times, one of a succession of editors who came and went during the grueling years of the last decade; he lasted about 14 months. O’Shea took a Harvard fellowship after leaving the Times, then, in 2009, started the Chicago News Cooperative, which currently supplies full pages of Chicago news to The New York Times each week. O’Shea will speak at Johns Hopkins University on Nov. 10. City Paper spoke to him by phone on Nov. 3, and what follows is a slightly condensed and edited account of that conversation.

CITY PAPER : What is the Chicago News Cooperative?

JAMES O’sHEA: The idea was to create a nonprofit . . . membership cooperative, so we’re not asking people to pay for content, we’re asking people to join a cooperative, one of the benefits of which will be a web site with what we call news interest networks—using social networking to organize around an interest in the news. So if you’re interested in, say, education in Chicago . . . we would provide you with detailed education coverage that you can’t get anywhere else because newspapers have been cutting back.

CP : And you have like 25 reporters or something?

JO: No, we have about 20 people writing for us, about 15 to 18 of them are reporters or editors, but the bulk of them are freelance.

CP: So, how’s that plan working?

JO: We’ve been in existence for just two years. We kind of had to change our plans a little bit. We entered into this agreement with The New York Times, which was looking for a local partner to supply copy for the paper that circulates in the Midwest. So we said OK, we’ll have money from content sales, and we’ll get some money from memberships, we’ll get some money from sponsorships, and donations. So, we are just now kind of at the point. The Times wanted to get up and running fast, because they were worried that Rupert Murdoch was going to put local content in The Wall Street Journal [in Chicago], like he did in New York. So we had to move quickly, and we didn’t raise the kind of [seed] money we had planned. . . .

CP : So you’re saying you would have liked to have gone around shaking the can for a year or two before you started posting stories, just to build up some cash?

JO: Yeah. It’s probably wise to get about three years’ operating funds in the tank before you start. We just basically have less than a year. So we’re kind of gambling that we’ll be able to raise the money. So right now we’re kind of at a critical phase.

Cp : What are the lessons for everybody in the Tribune Company bankruptcy?

JO: One of the lessons that I would have learned out of it was don’t put all your eggs in one basket. [Newspapers generally] became so reliant on advertising revenue . . . so when your big source of revenue goes out the door and you tell people, “Well, now you’ve got to pay for [web] content,” but you’ve already conditioned them to not pay for content. . .

Secondly, I kind of viewed a lot of these guys as they kind of lost their soul. You really exist to serve the public. That’s not just something you happen to do to make money. Your whole idea is, I’m going to go out and produce good journalism, and if I produce good journalism I’ll have readers, and if I have readers I’ll have advertisers . . . and income.

CP : By “these guys,” you mean . . . ?

JO: I’m talking about the people on the business side of the paper. The financial guys. They were kind of performing for Wall Street.

CP : What was your opinion of Ben Bagdikian’s [1983] book The Media Monopoly?

JO: When I first joined the Tribune [in 1979], it was still a private company. And I got to the point where I thought, if you can run a paper and still make a lot of money that’s fine, just so long as you’re producing good journalism. We [journalists] didn’t pay enough attention to the kind of arguments that Bagdikian was making. In the newsroom you hear [about], and I talk about it in this book, the wall between business and editorial, and we were pretty comfortable with that. It shielded us from having to think about making it go as a business. So our voices were not really heard that much, because we weren’t in the room, because we chose to stay out of the room, or somebody chose to keep us out. And I think that was damaging, because the business [side] needed to hear from journalists, and journalists needed to weigh in on business decisions, and [journalists] should have become aware of the threats to the business model that developed. We didn’t take them seriously enough until it was too late.