The Deal from Hell

Gayle Reaves-King

The Deal from Hell: How Moguls and Wall Street Plundered Great American Newspapers

James O’Shea

Oct. 21, 2012


It’s considered a bit déclassé these days to make comparisons to the Nazis: It’s a cheap, sensational way to criticize anyone and anything.  Nonetheless, that is the comparison that occurred to me repeatedly as I read The Deal from Hell: How Moguls and Wall Street Plundered Great American Newspapers, James O’Shea’s indictment of the bankers, owners, and executives who brought some of the finest and most powerful news organizations in this country to their knees. 1

The comparison that formed in my mind was not about fascism or racist ideology, however. It was about power and how putting too much of it, unfettered, in the hands of too few people leads to many horrific ends. Those ends always –– if not from the first then unerringly somewhere along the way –– include personal greed that can grow to justify killing people, newspapers, river systems, democratic systems of government, and, of course, ethics.

 The Nazis weren’t just about ideology and territory. At most levels, they personally enriched themselves, exchanging much of their humanity for the ability to take whatever they wanted.  As Lord Action put it much more succinctly, power corrupts. And that’s what seems to have happened at many points along the way of this tawdry newspaper tale.

O’Shea was an award-winning reporter before taking over management of the Chicago Tribune’s national and foreign news operation. He went on to become managing editor of the Trib during a period when the paper won six Pulitzer prizes. After the merger of the Tribune Company with The Times-Mirror Company in 2000 –– and after the Los Angeles Times became a revolving door of editors and publishers –– he was brought in as editor.

A year later, real estate tycoon Sam Zell bought the company with ill-conceived debt financing, plunging it into a financial and journalistic tailspin from which it has yet to recover.  As the author told The New York Times’ David Carr, he was stunned to find that powerful bankers “were basically doing billion-dollar loans with a wink and a nod.”2

His position gave the author great insights and insider information, but it also resulted in a myopia that weakens the book. “The investigative reporter O’Shea would surely have asked the editor O’Shea –– were they not one and the same –– how he could have been taken aback” that his Tribune Company bosses would start pressuring him for staff cuts as soon as he landed on the West Coast, Geneva Overholser wrote in her review for the Los Angeles Times.3

The book is a detailed, deeply researched indictment of how corporate greed and mismanagement led to massive debacles for the Times, the Chicago Tribune –– and, the author believes, for many other newspapers. What is killing American newspapers, he wrote, isn’t just the Internet and declining circulation, but “the lack of investment, the greed, incompetence, corruption hypocrisy, and downright arrogance of people who put their interests ahead of the public’s.”4

True, many American newspapers are going through terribly hard times for reasons other than high-level financial malfeasance on the scale of that perpetrated by the Tribune and Times-Mirror dealmakers.  Even if the merger and sale to Zell hadn’t happened, suggested Jack Shafer in The Washington Post, “Wouldn’t the Tribune and Times-Mirror newspapers still have had to cut employee perks, staff, bureaus, circulation, and quality to prevail? The answer is obvious.”5

 O’Shea acknowledges the other factors that have led the press into such deep trouble. As he wrote in a paper for the Joan Shorenstein Center on the Press, Politics and Public Policy that was a precursor to the book, “Journalists across America were in denial  about the problems newspapers faced, but nowhere was the disavowal more glaring and public  than at the Los Angeles Times.”6

That, however, doesn’t let these particular villains off the hook. How do you not bear responsibility for a decision, for instance, that systematically removed veteran newspaper managers from the company hierarchy and replaced them with people like Randy Michaels, a radio manager with a long list of sexual harassment complaints in his file who wrote a nine-page plan for the Tribune Company that never once mentioned the word journalism?7

Then there’s the email that O’Shea unearthed from bankruptcy court files, in which an analyst with JPMorgan Chase & Company described JPM’s strategy in the Tribune deal as hit-and-run: “We’ll s_uck the sponsor’s a$$ as long as we can suck $$$ out of the (dying or dead?) client’s pocket, and we really don’t care as long as our a$$ is well-covered.” 8

            The analyst may have been a lower-level person, but a thousand other factoids in the book and in the public record these days show how morally bankrupt much of American corporate culture has become, especially at the very top . And, not surprisingly, how the ownership of newspaper companies has been such a disastrously poor fit. As Michael Milner wrote in Chicago Reader, “The larger point O’Shea is making feels right: Nonjournalists rarely get the business of journalism.” 9

O’Shea’s style is conversational, and his facts are so fascinating that they keep the book moving along.  Even great quotes and revelations don’t save weak writing, however. The book is larded with clichés, including several that Shafer pointed out“When he writes that somebody’s eyes ‘twinkle,’ I found myself wanting to poke mine out,” the reviewer said, and I had to agree. The failings would have been less wearisome in a newspaper article; at book length, it is wince-inducing.

In the end, his bill of particulars against corporate ownership of the news business goes far beyond the corruption and greed documented in The Deal From Hell.  The fundamental change has been that of owners and managers reducing their companies’ mission to that of any widget-maker looking out for the next quarter’s profit and their own pocketbooks, rather than as operators of an industry that is a key to the health of democracy.


References (Chicago Style)


1. James O’Shea, The Deal from Hell: How Moguls and Wall Street Plundered Great American Newspapers (Public Affairs, 2011).

2. David Carr, “Ugly Details in Selling Newspapers,” The New York Times, June 19, 2011, accessed Oct. 19, 2012, from

3. Geneva Overholser, “Book Review: The Deal from Hell by James O’Shea,” Los Angeles Times, June 28, 2011, accessed Oct. 19, 2012 from

4. O’Shea, Deal From Hell, 12.

5. Jack Shafer, “Jack Shafer reviews James O’Shea’s ‘The Deal from Hell,’ ” The Washington Post, June 24, 2011, retrieved Oct. 20, 2012, from

6. O’Shea, “Up Against a Saint and a Dead Man,” Joan Shorenstein Center on the Press, Politics and Public Policy, Discussion Paper Series, 2011.

7. O’Shea, Deal From Hell, 323.

8. Ibid, 265.

9. Michael Miner, “James O’Shea narrates the Tribune Company’s epic collapse,” Chicago Reader, June 30, 2011, accessed Oct. 20, 2012, from



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