James O'Shea
James O'Shea

Days before my review copy of James O’Shea’s The Deal From Hell came in the mail, a friend who’d read an excerpt of O’Shea’s account of the Tribune Company-Times Mirror merger and its calamitous aftermath e-mailed me to rip the author.

At issue: O’Shea’s failure to be up-front about the friendship between his ex-boss Ann Marie Lipinski, the Tribune‘s editor at the time of the merger, and Bill Pate, a lawyer who helped orchestrate the deal in which Sam Zell took over Tribune Company in 2007.

“Odd, isn’t it, that while writing more fully about Zell’s ‘golden boy’ Bill Pate . . . than anyone has to date, he never mentions that Pate and his wife and Ann-Marie and [her husband] Steve K. are BFFs and have/had summer property/houses together in Michigan,” my friend complained. “The cliques in that place sure do last forever, huh?”

O’Shea was Lipinski’s managing editor and has “incredible respect” for her. My friend has less. Pate is a secondary figure in O’Shea’s book, and only once, in my view, does its failure to acknowledge the lawyer’s close friendship with Lipinski taint the narrative. This comes when Zell has just taken over and O’Shea is about to be fired as editor of the Los Angeles Times (the job he’d been promoted to in 2006 from the Trib). Lipinski and Pate were “in regular contact,” O’Shea tells us, and after a trip out of the country Pate writes her asking for an update. “When she replied that everything was OK in Chicago but there were ‘storm clouds out West,’ Pate never responded.”

This makes Pate and Lipinski sound less chummy than they were, and if you suspect O’Shea of shielding her from just criticism, here’s the evidence. What’s wrong is not much more than a nuance, but when insiders like O’Shea write about billion-dollar business deals gone bad, in-the-know readers cut them no slack on nuances.

Reading O’Shea’s book, which I enjoyed and admire (but then, he used to sit on the board of the company that runs the Reader), I began to think about the thankless assignment he’d given himself. An insider’s book is supposed to be authoritative; yet an insider was a player himself, so how can we trust his account? Every detail that doesn’t make the final draft will be held up by somebody as evidence of the author’s self-serving manipulations.

Many an insider is silenced by the nondisparagement contract he signs in exchange for a sweet exit package. Because O’Shea refused to sign his, we have The Deal From Hell, his personal experiences fleshed out, he says, by “a hell of a lot of reporting.” He tells me friends read it beforehand to circle the places where he sounded too much like a guy grinding axes. They got rid of those, but here and there they’ve let him sound impossibly noble:

“At all costs, I had to protect the integrity of the institution I ran and, by extension, the news and pass on to my successor a better paper than the one I had inherited. If the credibility of the newspaper and the respect with which it was held in the community diminished on my watch, I failed my community, my craft, my staff, my newspaper, and its owner, even if the owner [Zell] failed to appreciate the distinction.”

O’Shea’s occasional gusts of high-mindedness would have benefited from some sort of reality check. I’d like to have seen Tribune Company, whose bosses didn’t get it about journalism, measured against some more successful media behemoth whose bosses did. But newspapers everywhere have foundered, so how much better would it actually have gone for Tribune Company if, say, Jack Fuller, a former Tribune editor, had become CEO in 2003 instead of Dennis FitzSimons, a product of broadcast sales? A lot better, O’Shea thinks—but cannot show. In time, perhaps he’ll be able to: O’Shea believes some papers, such as the New York Times and Britain’s Guardian, will survive the wilderness years because they’ve kept the faith—neither has “really given up on the fact it’s a journalistic organization.” As for Fuller, who ran the company’s newspapers but lost out to FitzSimons for the CEO job and resigned in 2004, O’Shea can simply say he “was a journalist at heart and we were better off when he was there.”

Some readers will reject O’Shea’s idea of Fuller as any kind of paragon. A number of Tribune staffers hold Fuller responsible for mishandling the 2000 Tribune-Times Mirror merger, which he played a central role in negotiating. O’Shea does not; and he reminds readers that for its first few years the merged company thrived. Yet his book notes that due diligence lasted two days, the price paid was “far too high,” Tribune Company didn’t take seriously a billion dollars in potential Times Mirror tax liability until the government demanded its money, and the Chandler family, which controlled Times Mirror, was left so empowered by the deal that when the stock started to slide a few years later and the Chandlers wanted their money out, they were able to force a sale. Enter Sam Zell.

The larger point O’Shea is making feels right. Nonjournalists rarely get the business of journalism. It looks like any other kind of industry where a product is made and sold and tailored to its market—but it isn’t. O’Shea mentions readership surveys FitzSimons conducted in LA. “The average reader in Southern California ranked his or her top news interests in order of relevance as local, Southern California, national, and news about the economy. But if you overlaid onto the charts the interests of the Times’ most dedicated readers, they reflected a different set of priorities: national, international, national government, politics, and arts and entertainment.”

Neighborhood papers delivered local news, says O’Shea; Times readers really wanted a paper they could think of as “the voice of the west and America’s eyeballs on Asia.” He says, “I felt people in LA cared much more about their paper than people in Chicago did. They really cared, and they were worried about it.” When the Times started running ads on page one, the head of the county board of supervisors wrote the Times asking it to stop. “That’s extraordinary,” says O’Shea. “I came away saying this paper should be owned by people in the community. Not by huge chains. Every newspaper should be owned by people in the community. They can make of it what they want of it.”

The orders from Chicago were to focus on local coverage and slash budgets and staffs, first to ramp up profits and later to salvage them. When FitzSimons did this O’Shea considered it folly, and he hoped Zell, whom he judged a far shrewder man, would know better. O’Shea said in his departing words to the Times staff, “I believe that when Sam Zell understands how asinine the current budgetary system is, he will change it for the better because he is a smart businessman and understands the value of wise investment. A dollar’s worth of investment is worth far more than a barrel of budget cuts.”

But Zell turned out to be thin-skinned, crude, and profane, and soon “revealed his fundamental misunderstanding of the business he now controlled.” George de Lama, the Tribune‘s managing editor after O’Shea, found Zell so disparaging of Latinos that he resigned. Randy Michaels, a creature from Clear Channel Television who ran the Tower for Zell, wrote a nine-page battle plan full of blather like “Empower opinion leaders who buy into the new vision” while not using the word “journalism” once.

O’Shea writes that Michaels ruled through “cronies” and underlings who “swore allegiance” out of fear. One of the stories that eventually helped chase Michaels off the premises had a security guard discovering him on a terrace of Tribune Tower enjoying a blow job performed by a woman who worked there. It’s a story that went around the Tribune before O’Shea put it between covers, and someone in the Tower who talked to the woman (O’Shea doesn’t name her) has told me she denies it. But O’Shea is sure enough. “I had three sources on it,” he says. “I had a letter about it. I had the person in charge of the Tower. And the person in charge of the security guards. The [guard] went out there [onto the terrace] and came back and reported it to his superiors. I know that’s true.”

Michaels and the people he brought in were such hooligans that Gerould Kern, the opportunist (in O’Shea’s telling) who held the title of editorial director of Tribune Publishing, “called Lipinski and said he was sick of the foul language and compared them to Brownshirts, using words like ‘evil’ and ‘stupid.'” But Lipinski quit and Kern got her job, at which point, O’Shea writes, allowing himself one of his book’s few snickers, “those Brownshirts seemed more like khaki.” De Lama was replaced by someone from RedEye.

Tribune Company entered bankruptcy in 2008 and hasn’t emerged yet. Michaels and his boys were run off last year after a New York Times article recited their antics. O’Shea heads the Chicago News Cooperative, which he launched in 2009. And Kern just refashioned the Tribune along the lines O’Shea thinks should never have been abandoned—adding typographical elegance, content, and intellectual heft.

E-mail Michael Miner at mminer@chicagoreader.com.