James O’Shea, former editor at the Chicago Tribune and the Los Angeles Times, was close to the center of the successive storms at the Tribune company, from its ill-fated 2000 merger with newspaper chain Times Mirror—then owner of the LA Times and Baltimore Sun—to the disastrous 2007 takeover by a group of investors led by Sam Zell, leading to the company’s eventual bankruptcy. O’Shea gives his account of the company’s decline in The Deal from Hell , published in 2011.

After leaving Tribune, O’Shea founded and managed the Chicago News Cooperative, which folded last year. Now, Tribune has reentered the limelight—the company has emerged from bankruptcy, and its newspapers may be purchased by the Koch brothers. In an interview with CJR, O’Shea spoke on a range of topics, from the bankruptcy and the Kochs, to the company’s newspaper spinoff, and the Sun-Times photographer layoffs.

The Tribune company emerged from bankruptcy at the end of 2012. Is it truly in better financial shape, and to what extent were more serious decisions about the company’s financial assets kicked down the road?

Well, I think splitting the company into two [the newly expanded television arm of Tribune is being split from the newspaper arm] is basically a strategy of creating one company with the assets that the existing owners consider to be good, and one company with the assets the existing owners consider bad. The broadcasting company is clearly the one they think has the good assets, because they put the digital assets there, and by doing that they diminish the value of the newspapers. They probably couldn’t sell the papers as a group without the digital, but they could still sell them individually.

In The Deal from Hell, you seem to say that tensions after the Times Mirror-Tribune merger between the most powerful papers in each former company—the LAT and the Chicago Tribune, respectively, made the union a risky proposition. Do you think it was doomed from the start? If so, why?

Well, I don’t think it was doomed from the start, but I think Tribune made a mistake by not appointing someone from Chicago, who knew the lay of the land and knew the personalities involved, to a high position in the editorial ranks at the LA Times. The distance between LA and Chicago surfaced almost immediately, when the Tribune guys went out there and got critical of how the Times Mirror people ran LA, but tensions really accelerated was when you get into 2004, 2005, when the LA Times began seeing declines in its revenue, especially when the movie industry started pulling back on their advertising. This loss of revenue meant Chicago started pressuring LA to come up with cuts,and LA’s looking at Chicago and they’re not seeing the same kind of thing happening at Chicago. Meanwhile, Chicago’s looking at LA and saying, their editorial staff is 50-percent bigger than ours—they should be cutting.

One of the critiques of the Times Mirror and later Tribune—articulated most prominently by David Simon in the final season of The Wire, is that the newspapers badly served their cities by focusing too much on working issues into prize-mongering “five-part series.” Do you feel his critique is justified?

It’s an interesting question. I happen to believe very strongly that a newspaper should be a public-service institution, and everything that’s in the paper doesn’t have to be read by everyone. But there has to be a value to it, so I disagree with him. Those series, though they won prizes and, in cases, probably were conceived with prizes in mind, had a valid public-service purpose, and they gave the paper credibility.

A large part of The Deal From Hell is an indictment of Sam Zell and his acolytes, and the culture he brought to Tribune. Are the people that Zell installed still in decision-making roles at the company?

It depends on what you call the ‘Zell acolytes.’ If you are talking about Randy Michaels, he’s clearly gone, and Nills Larsen, who was running the broadcast side, he’s gone, but he did a fairly decent job there. Some of the existing Tribune people who were put into positions by Zell, like Gerould Kern, the editor of the Tribune, are still there, but they aren’t really his acolytes.

Do you feel that Tribune overall has changed course for the better since you left the company?

Abraham Moussako is a former CJR intern. Follow him on Twitter at @AMoussako.