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

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In 2000, after the Tribune Company acquired Times Mirror Corporation, it comprised the most powerful collection of newspapers in the world. How then did Tribune nosedive into bankruptcy and public scandal? In The Deal From Hell , veteran Tribune and Los Angeles Times editor James O'Shea takes us behind the scenes of the decisions that led to disaster in boardrooms and newsrooms from coast to coast, based on access to key players, court testimony, and sworn depositions.

The Deal From Hell is a riveting narrative that chronicles how news industry executives and editors--convinced they were acting in the best interests of their publications--made a series of flawed decisions that endangered journalistic credibility and drove the newspapers, already confronting a perfect storm of political, technological, economic, and social turmoil, to the brink of extinction.

416 pages, Hardcover

First published June 28, 2011

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James O'Shea

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Displaying 1 - 21 of 21 reviews
Profile Image for Ethan Grove.
22 reviews
February 2, 2021
"The Deal from Hell" is a little bit of historical perspective and lived-history, an exploration of two once-great institutions' past and the people who made them, and a reminder of some characters who and moments that unmade them. It reopens past traumas and anxieties, and exposes the avarice and greed that inspired terrible decision-making by a lot of people. It's very good, but infuriating because -- as we see so often -- it didn't need to be like this, or this bad.
Profile Image for Pete Nickeas.
22 reviews2 followers
January 14, 2013
Fascinating. Interesting account of how things happened mixed with some general news media observations.
Profile Image for David.
208 reviews638 followers
October 16, 2013
Before I dive into this completely irrelevant and fictional review of Shea's The Deal From Hell, let me briefly discuss some maybe unknown information which is relevant to this book, and to the goodreads community:

1. In 2000, the enormous merger of two of the country's largest newspapers was put in motion. Those companies were the Tribune Company, most notably the publisher of the Chicago Tribune, and the Times Mirror Company, notable publisher of the LA Times.
2. The two companies were incompatible culturally, though financially it seemed (on paper) that the merger would be an excellent success.
3. The merger was effected by large personalities at Tribune, which won over the blasé insouciance of the reigning Chandler family heirs who owned Times Mirror. Some large-ego investment bankers brought the deal together and Shea's opinion is basically that they are evil. The Tribune's newly anointed CEO, a Wall-Street pedigree, Mr. Madigan, cut costs and pursued acquisitions with blind Macbethian ambition. Which is to say: scrambling and self-defeating.
4. The largest merger in newspaper history was a complete failure due to the different objectives and cultures between the rigid and cost-oriented Tribune, and the West-Coast content-oriented LA Times. The combined Tribune Co. went bankrupt, was bought out by method of a leveraged buyout, and subsequently went bankrupt again. It is still in bankruptcy proceedings half a decade later.

An interesting fact: among the living heirs, who sold out the LA Times in 2000 to Madigan and his Wall Street cavalcade: none other than Otis Chandler, the co-founder of GoodReads. Now you know.

That said, now proceeds a totally unrelated fable about the life and times of an online book community called GoodBooks, and the tragic merger with the larger bully-company, an online retailer famous for crowding out small businesses and brick-mortar bookstores, Yangtze Co.
****
CAVEAT LECTOR: the following is in violation of the GoodReads terms of service, since it is not directly related to the aforediscussed book, A Deal From Hell by James O'Shea, but is rather a illustrative parable derived from the lessons learned therefrom.

GoodBooks: A Deal From Hell: a fable

In a land not so far, and a time not so long-ago, there was a small bookish community, which found pleasant pastures in the electronic Elysium of the internet. This community, which grew and grew, grew near and far and up and down, and more people and more books were always showing up: this community was called GoodBooks. And it should be noted that this GoodBooks, this is a fictional community and not at all related to a similarly named entity.

Who started GoodBooks? That's not at all hard to say! His name was Otis Chumpler, and he co-founded this place with his lovely wife, Elisabeth. Mr. Chumpler was a good-looking, bookish man, smart as a whip, with a thick chevalure like an Iowan field of wheat, a strong angular jaw, and a brazen complexion from the seductive sun of lush Los Angeles beaches and jaunty jogs in the San Francisco parks. He was a young man, still, though he and his wife had found wonderful success in their GoodBooks endeavor, and despite its minor mars and mistakes, it was a good place and it had good people who read good (and sometimes not-good) books. They were happy.

Otis Chumpler had a secret. Well it wasn't so much a secret as it was a maybe unknown trivium. He was the son and heir to the Chumpler fortune! You see, the Chumplers had long owned the Los Angeles Gazette and their many subsidiaries - really, it had been a veritable empire of thin grey Gazettes and flimsy faded Chronicles and Times, and even a west-coast Globe, or two! Otis, with his brothers and sisters had sold that huge paper fortune for a fortune of a different paper. Looking on the Gazette Building, a big shiny mirror in Los Angeles, like the lovely Emerald City, but made rather of diamonds! Looking at this fortress, Otis saw his past reflecting like his future, though he didn't know it. The Gazette building was a tall structure! And the grande glass elevator had given Otis his name, for he had been conceived in that very Otis elevator thirty-some years before! Or maybe he wasn't, it's quite impossible to know the point and place of conception.

GoodBooks grew and grew, and kept growing, and anyway who knew there were so many bookish people! The staff at GoodBooks were passionate and mostly handsoff, though responsive and kind, interested and warm, always adding content to appeal to the wide interests and nooks and crannies of the many shelves of the many patrons and patronesses of GoodBooks. And still as it grew and grew, everyone was happy.

All this growing! The Chumplers of course were happy. And readers were happy, happy to see more faces and reviews and more books being ever and ever added. And the whole places was a small internet haven for those bookish folks.

Meanwhile, in another nook, a much larger nook, in fact not a nook at all but rather a continent or a vast ocean or an enormous crater, of the internet there lurked a sort of e-commerce beast, Yangtze Co! It wasn't an evil beast, there are no evil companies, just big ones and small ones and medium sized ones, but this was a big one. Yangtze had been buying up these small nooks and crannies of the internet, little pockets, really, for holding money, and anyway they brought off these little pockets with enormous success, and anyway they had lots of pockets and big pants with plenty of room for more. Well anyway, all these little things that grow and grow and start to become less-little things and even sometimes big things, attract attention from big beasts like Yangtze! Once your a big beast it is hard to grow, your bones and you skin and your clothes just don't allow for it! And so big beasts are always looking to add pockets.

Yangtze eyed GoodBooks, counted off some cash to Chumplers and soon enough like the sun down behind the mountains, GoodBooks was a big bookish pocket on the vast-waisted pants of that Yangtze beast.

At first there was some rebellion. Who knows why? Some people are always afraid of big beasts, and always will be, and they flee big beasts and live quietly with small beasts. Others waited, and frankly others didn't notice at all! These last were much too absorbed with their Sixty Shades of Sex and Hunger Dames shipments, fresh from the cardboard Yangtze-logoed boxes! The miracles of e-commerce! But the few watchful remained vigilant. And for a while nothing seemed to happen. GoodBooks was quiet. Some left, though, and they were missed.

But then, all of a sudden, something happened. Reviews began to disappear! Where did they go? Perhaps somewhere deep in that pocket, or perhaps an even deeper darker abyss, but anyway they were gone now: irretrievably gone. And when the reviews began to disappear, so too did the reviewers! What an exodus! It would seem that Yangtze Co. took some umbrage with the way things were run at GoodBooks. It wasn't a well oiled machine, maybe it wasn't a machine really at all, but Yangtze was a well-oiled machine, and if fingers are lost in well-oiled machines then fingers are lost, but the machine continues. And so fingers were lost, but they were only fingers. And the Chumplers were happy: they had more paper than ever before! and also, anyway, they had all of their fingers. Yangtze was happy, and they were rubbing together their greedy fingers. Or rather not Yangtze, but the people at Yangtze, because after all even big beasts don't have fingers to rub! But the readers, the readers were not happy, and many were missing fingers! It can be very hard to read when one is missing too many fingers.

And the exodus continued. Reviewers left or put up feeble rebellions. Big beasts are so hard to beat! How ever did they overthrow that fat old beastly Louis of France? and his wife with the big fat hair? and then the really very fat Robespierre? Such big beasts! But not ever so big as this Yangtze beast, for you could never get hold of it, you couldn't beat it or shackle it or throw its big beastly head in a guillotine or even get on the phone with a beastly person, it was everywhere but no where! A big ghost of electric data, dropping from its many posteriors little packages stamped with a smile, but no face! just a Cheshire smile. And it took in its many mouths the paper from many people and this was what the big old beast ate, and it always had things to eat, living on a healthy diet of paper and of fingers.

And the beast went on eating, and the best, the best went away, or stayed and fought. But it's no fun fighting a beast, even if you're one of the best. But maybe one day the beast will get sick of fingers? The best can only hope!
Profile Image for Marguerite Hargreaves.
1,424 reviews29 followers
December 22, 2020
The Deal From Hell does a thorough job of analyzing the demise of newspapers, particularly those owned by the Chicago Tribune, one of which was my employer for the better part of three decades.

James O'Shea worked as a reporter and editor at the Tribune and had a front-row seat and a role in the debacle that unfolded after the Tribune bought the Times Mirror Co. and the Los Angeles Times. My newspaper, the Daily Press, which O'Shea incorrectly identifies as the Newport News (Doh! Newport News is the city where it's located), was bought by Tribune in 1986. The dynamics that played out were similar, however. The newspapers began their lives with local owners, who for the most part did a decent job as stewards of the businesses and journalists' mission to serve the public with information and community leadership.

Tribune had become a public company in 1983. As such, it brought an obsession with profits to local institutions where profit had been a goal, but one that never was a focus in the newsroom. Tribune sold off assets (cable television companies, real estate and other holdings.) All of the Tribune newspapers were given profit percentages that felt like shakedowns to those of us who had to meet or exceed them.

We closed bureaus and stopped covering communities and regions. (We told the communities and residents they didn't matter.) We reorganized the newsroom in an effort to become a more flexible and adaptive news-gathering organization. We put ads on the front page and charged a king's ransom for obituaries. We made the newspaper smaller and less relevant and dumbed things down. (I believe that's helped fake news, conspiracy theories, racism, sexism and other isms to find new life and flourish in recent years.) And we began a series of layoffs and buyouts that continue. We told a generation or two of journalists that their hard-won experience was irrelevant and worth nothing.

O'Shea synthesizes a lot of information here. He also takes some cheap shots and settles a few old scores. Because of the necessary focus on institutions, the reader loses sight of the thousands of principled, skilled people cast aside by greedy and crass overlords. I'd love to learn how their stories continue.
Profile Image for Dan Seitz.
449 reviews4 followers
November 20, 2020
The next time somebody blames Facebook or Google for the current situation of journalism, make them read this book. Well before Zuckerberg came along and before Google became a force in our lives, well before the internet in fact, O'Shea uncovers the dirty dealing, lies, and rotten decisions that exposed the newspaper and broader publishing industry to vastly more risk from the internet than was necessary. And, once that fell apart, in came venture capitalists with more money than sense.

It's not a cheerful read, but if you want to understand how a seemingly mighty industry could fall apart with such a painful swiftness, it's a must read.
Profile Image for Brad.
91 reviews9 followers
December 11, 2011
O'Shea may think he's written a book about how profit-driven, ego-centric people ruined some of the nation's largest papers, but that's because his own biases are at work here.

Actually what this book does is paint a picture of why it's hard to run a newspaper as a for-profit business with the goal of constantly increasing revenue.

He belittles the bosses that want to print the stories "people want" involving celebraties and gossip rather than important news of conflict, politics, and holding government accountable. But he side steps the question of paying for that coverage.

In a perfect world, readers that want to support different types of news would pay for the publications where it exists. Or advertisers would pay to reach those readers. But one problem that people consistently ignore is that advertisers have long been throwing money away on traditional media because there's simply no way to gauge how readers are reacting.

Online ad rates aren't lower because they're less effective, but because they're more effective... but they don't pay enough to support the kind of journalism great papers have produced over the years.

Whether intentionally or not though, he makes a pretty strong case for a public broadcasting style form of member-supported public interest journalism.

Update: OK, I got to the end of the book, and it turns out O'Shea *does* realize that the problem is that journalism emerged as a profession with a non-profit ethos and a for-profit business model. He's now heading up the non-profit Chicago News Cooperative, which I hadn't realized when I started reading. It may very well be a model for the future of news.

That said, it still bugged me how much he belittled local news coverage and praised national and international reporting as a matter of course -- he also tended to paint all online news with the same brush as second class citizens, even though he's now heading up an online news outfit.

He also largely paints a problem without offering a solution... and misses some of the problems in the process. Yes, newspapers have always been delivered to consumers at ridiculously cheap prices considering the costs of printing and distributing them, not to mention reporting the news.

But even if ad revenue wasn't declining, people that have gotten used to getting news for free or cheap online and through broadcast media would probably be drifting away from paying for the print editions.

This book is definitely worth reading if you're interested in the current state of the news industry, but it shines brightest when O'Shea is recounting his own personal experiences in the center of the storm. It's kind of dry reading when he slogs through the financial management of the papers he's talking about and the finer points of the deals that were made.

Like any good news story, it's the people that make this book interesting, not the numbers.
Profile Image for Dawn.
767 reviews38 followers
October 18, 2011
The Deal From Hell by James O’Shea is about the changes of journalism. The truth is that news media is changing and it is in trouble. People rely on honest journalism not a quick by-line but actual journalism where someone has researched a story and found evidence and support then that journalist will retell the tale so everyone can understand and be informed. Instead our world is becoming increasingly full of sound bites and quick articles from the wire.

James O’Shea attempts to paint a picture on how the media has been transformed due to big business. I think he gives a face to what most of us already know. Personally I still recall how the white house leaked a story to a journalist.. then the journalist wrote the story …then the white house said the story was credible due to the news article – yep that type of circle represents what we seem to be losing, oh and if you are looking for that tale it is not in this book.

I found the book to have a good flow and it was well done. There were parts where I wished he went into more detail, like after the initial press room cuts what happened to reporters do they go somewhere else change careers? Are those that are left forced to write more? The tale Mr. O’Shea tells about how the Tribune Company started to fall in part due to the loss of advertising revenue and in part to the mismanagement of the paper itself. The book leaves one to wonder in times like these where we so desperately need unbiased news media if not papers who will fill that role?
Author 6 books9 followers
November 16, 2011
Boy, this stuff sounds familiar. Not because I was following the trials and Tribuneilations of the newspaper business over the last few years -- I wasn't paying that much attention -- but because so much of it sounds like what has gone around me for the last year or so. This is a great example of what happens when metrics fail to meet vision.

O'Shea tries to make a case that the "moguls and Wall Street" destroyed the newspaper business over the last decade. I'm not sure he succeeds, though he does prove that the financiers and budget-cutters made things worse, not better. But communications have undergone a structural change over the last fifteen years, and newspapers have severe competitive disadvantages. It costs a lot to put words on paper and deliver them to a doorstep, and there's no reliable feedback mechanism to learn which stories and ads reached their audience. That's an industry killer. Journalism has a bright future in the new media, but the 20th century newspaper is probably as dead as vinyl.

This takes nothing away from the book, which is the kind of thoughtful eyewitness reporting that you'd expect from an old school newspaperman. It is also a powerful cautionary tale -- not so much about how bad choices can ruin the newspaper business -- but about the impossibility of doing anything innovative or creative if all you pay attention to is focus groups and the quick buck.
Profile Image for Tim Jin.
843 reviews4 followers
December 6, 2013
When I think about the newspaper, I always assume as old media, but most of the population in the world get their news on print. I am writing this a few days after the bombing in Boston. Ironically, the next day after the tragedy, I saw more people reading this headline on print, instead of viewing it on a glowing tiny screens.

Maybe the newspaper should only print the paper when something major happens in our society. Most day to day news are just fluff pieces that is just taking up space. Do we have to know last night's sports scores, outdated stock quotes, the weather, or Lindsay Lohan. How is this news worthy?

I can't remember when I bought the newspaper. You actually have to go out of your way to buy the paper and pay for a subscription and having to deal with the physical paper is just dumb. It's not worth my time to recycle the paper.

"The Deal from Hell" is a good read. I actually learned a lot for listening to James O'Shea's experience at running the newspaper. The newspaper is an old boys club, where ink on paper is becoming a dinosaur.

I just hope that a Postmaster will write a book on the Post Office and see how they have no business and where 100% of the mail that they deliver is just SPAM.
Profile Image for Carol.
386 reviews19 followers
November 2, 2011
Two deals, actually, are described in O'Shea's book. One is the Tribune Company's purchase of the Times Mirror company, which made the Los Angeles Times the Chicago Tribune troubled siblings, and the other was the purchase of the Tribune by uberfinancier Sam Zell. O'Shea does a magnificent job of detailing both deals and their aftereffects. O'Shea shifts his narrative pace for each deal. The LA Times fiasco takes on a jack-rabbity stop-and-go feel as O'Shea talks of the caprices of the Chandler family and their need to see massive dividends from their Times-Mirror-Tribune shares. When he gets to the Zell era, the book becomes a suspenseful page-turner as the deals roller-coaster through banks and investment teams. And O'Shea has a bit of a horror writer in him too -- at least, that's the emotion I felt as I realized that no one who makes these multi-billion dollar deals really knows what they're doing.

Through his well-honed reporting skills and his experience in crafting interesting stories out of what could be dull and complex information, O'Shea proves that there is still a very pressing need for journalists who know what they are doing to keep doing their jobs.
Profile Image for Brian .
976 reviews3 followers
April 24, 2015
The Deal from Hell chronicles James O’Shea (former editor of the LA Times) experiences working for the Chicago Tribune and LA Times as the company transitioned from Wall Street firm to privately owned enterprise. In fairness to the author he admits at the beginning he will have his own biases regarding the role of journalists and newspapers. The spoiler is that he believes newspapers should focus on big issues of the day and not local issues or celebrity type stories. He also resents the internet a great deal and the changing ethos that emerged leading to a decline in ad revenues. That being said when you can get past some of the long winded rants and the righteous indignation of anything that is not the far left this book does offer some interesting insights into the newspaper industry and its decline. You will find yourself being engrossed in the story and wanting to see what happens next. Ultimately if you have an interest in the newspaper industry or want to understand its decline there are valuable insights here and it will make for a fun read.
Profile Image for Marnie.
128 reviews14 followers
April 29, 2012
Have you ever read a really scary book before bedtime and then been unable to sleep with the lights off? As an employee of the LA Times, this fits the bill for me. I'm not going to say it's an accurate book. I honestly couldn't say. I find it easier to do my job if I don't get emotionally embroiled in things I have no power to change, but it was certainly compelling.

The author is open about the fact that the book has a bias to it and it sometimes reads like a bit of a humble-brag, but he does a good job of weaving together the pieces of a situation that would be far too absurdist to pass muster in fiction, making it all the more engrossing as non-fiction.
Profile Image for Bill.
218 reviews5 followers
November 19, 2012
If you lived within the orbit of Tribune Co. or the L.A. Times within the last decade, this book will be interesting to you. It's a quick read with a number of fine anecdotes. That means it's mostly inside baseball, so if you're looking for great insights into the fate of journalism in the (sadly likely) post-newspaper age, you'll want to look elsewhere. O'Shea throws in a handful of mea culpas but little reflection on how the narrow hard-news definition of journalism he espouses might be a contributor to its decline right along with the Internet and the corporate barbarians who are on the receiving end of his hand-wringing.
945 reviews3 followers
March 5, 2013
Compelling story about the purchase of Times Mirror (LA Times) by the Tribute Company (Chicago Tribune) and then the purchase of the new entity by Sam Zell.

It is also a story of print journalism and the challenges facing the newspaper industry.

This book was part memoir, part history, part reporting, a mix that worked quite well. It paints a really depressing and concerning picture, a completely appropriate for me to have read at this moment.
Profile Image for Kevin.
Author 11 books4 followers
January 1, 2015
I enjoyed reading the story of the downfall of the Tribune (my hometown paper) and the LA Times. Many business stories are dull, but this one was not. It also touched on a couple of issues that I feel are very important: 1) If there is no journalism how will we know when the powerful (business or government) misbehave and 2) the prevalence of MBA / Finance leadership in our private sector has been, and will be, a primary cause of the decline of our country.
Profile Image for David Becker.
302 reviews4 followers
April 25, 2016
I suppose there's a good story here, about how the newspaper industry destroyed itself with a toxic stew of greed, short-sighted thinking, etc. But O'Shea most certainly isn't the one to tell it. He gets bogged down in details and buries any narrative drive in dull, workmanlike prose. Having worked in the newspaper business for many years, he did dome the service, I suppose, of reminding me of what preening, self-important gasbags high-level editors can be.
Profile Image for Garrio H..
8 reviews24 followers
August 22, 2016
I'm a little skeptical of some of the cause and effect lines drawn in the book but that's to be expected. James made it clear in the beginning of the book it would be written from a journalist's perspective. It was still a pretty fascinating look at the inner-workings of the newspaper business. I highly recommend checking it out if your into "sausage making" type books.
104 reviews1 follower
May 18, 2013
Powerful, almost heartbreaking, chronicle of the decline of a once-great urban newspaper at the hands of profiteers with little or no journalistic experience or appreciation for time-honored journalistic ideals.
6 reviews
June 30, 2011
Well-reported albeit biased insider look at the current state of print journalism and how it got here. Very easy to read. Recommended for journalism buffs.
6 reviews
August 16, 2012


Kinda wish there was more there about the deal itself, and about how Tribune was brought to bankruptcy under the weight of its own debt. But then he wasn't really there for that either.
Profile Image for g.
106 reviews19 followers
September 20, 2011
Journalism is dying. This guy is kind of self-obsessed.
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